Home Vacation Rentals By Owner In Cape Charles, VA

Showing 100 Of 309 Vacation Rentals
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$538.02

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Private Vacation Home

Steps away from Beach - Modern Coastal Retreat

Cape Charles, Virginia, United States

Summary:brbrAlways Sunny—a beautifully renovated three-story coastal retreat where classic charm meets modern beachside luxury. Every detail has been thoughtfully designed to create a stay that feels both elevated and effortless.brbrbrbrPlease SEE: Other Things to NotebrbrFor Area Details, Please SEE: The Neighborhood & Getting Aroundbrbr*This is a no pet/animal home.brbrbrbrThe Space:brbrAlways Sunny, Home Features:brbr• 4 Bedroom, 3 Bath - Available for up to 8 Guests!brbr• Free WiFi & Smart TVbrbr• A fully equipped, open-concept kitchen and dining area designed for hosting family dinners and coastal feasts.brbrbrbrSleeping Arrangements: brbr- Multi-Level Homebrbr• Bedroom 1 - Queen Bed located on the main level for easy access. Private ensuite.brbr• Bedroom 2 - King Bed located on the 2nd level, Twin daybed w/ trundle, direct access to balcony.brbr• Bedroom 3 - Two Twin Beds located on the 2nd level, perfect for children or friends.brbr• Bedroom 4 - Queen Bed on the 3rd level with private ensuite.brbrbrbrWelcome to Always Sunny, a coastal masterpiece in the heart of the Cape Charles historic district. This stunning multi-level residence, noted on the National Register of Historic Places, offers a perfect marriage of Americana nostalgia and modern coastal luxury on Virginia’s Eastern Shore.brbrbrbrFrom the moment you arrive, you will be swept away by the serene, small-town atmosphere and the proximity to the Chesapeake Bay. The water here is famously calm, the sunsets are legendary, and the beach is just steps away from your front door.brbrbrbrDesigned for those who appreciate refined living, Always Sunny features expansive indoor and outdoor spaces that invite relaxation. The home radiates a bright, airy energy, whether you are sipping morning coffee on the private balcony or hosting a family dinner in the open-concept living area. The gourmet-ready kitchen is perfect for preparing coastal feasts, while high-speed Wi-Fi and Smart TVs ensure you stay connected and entertained.brbrbrbrThe home comfortably accommodates up to 8 guests across three distinct levels with four elegantly appointed bedrooms and three modern bathrooms:brbrbrbrOn the main level, you will find a sophisticated Queen suite with a private ensuite bathroom, offering easy access and ultimate privacy. The second level features the primary retreat—a grand King Bed suite with a twin daybed and trundle, plus direct access to the balcony to catch the salt air breeze. Also on the second level is a bedroom with two cozy twin beds, ideal for children or friends traveling together. The third level serves as a secluded sanctuary, offering a Queen bed and its own private ensuite for maximum peace.brbrbrbrGuest Access:brbrChesapeake Properties by Portoro offers convenient self check-in, details provided 2 weeks (or less) prior to arrival by email and text message.brbrbrbr• Early check-ins or late check-outs: If the property happens to be ready earlier than the standard 4 pm check-in time on the day of your arrival, in most cases an early arrival option may be available when confirmed with the main office. Late check-outs must be confirmed with main office staff prior to the date of departure.brbrbrbrThe Neighborhood:brbrNoted on the National Register of Historic Places, Northampton County's Cape Charles offers one of the largest concentrations of turn-of-the-century buildings on the East Coast. The historic district and small-town atmosphere create a serene and inviting community. Enjoy the history and experience galleries, boutiques, bookshops, and beautiful beach! Cape Charles Town Beach is the only free public beach on the Easter Shore of Virginia.brbrbrbrThings to See:brbr• Local Experiences: Take a Boat Tour, Kiteboarding, Kayaking, Paddleboarding, Explore the Beach, Fishing, Golf, Hiking, Biking, Birding & More!brbr• Local Restaurants & Shoppingbrbr- Restaurants: The Shanty, Oyster Farm Seafood Eatery, E&O Pub, Pane e Vino, Ambrogia Caffe & Enoteca, Cravings, AJ's Grillbrbr- Shops: The Boardwalk, Table and Tonic Cape Charles, Cape Charles Candy Company, Love Letters, Gull Hummock Gourmet Market, Chessie's Toys and Games & more!brbrbrbrAnnual Festivals & Events:brbr• Crabby Blues Festivalbrbr• Annual Crab Slambrbr• LOVEFestbrbr• Sounds of the Shorebrbr• Festive Fridays, Cape Charles Winter Wonderland (Nov-Dec)brbr• Free Concert in the Park (Summer Season, very Saturday evening)brbr• Grand Illumination (Dec)brbrbrbrWe provide a full list of Things to Do & See and local Restaurants & Shops to experience for our guests including in a personalized Guest Manual in your check-in details provided prior to your stay!brbrbrbrNorthampton County Short-Term Rental Registration No. # A-000282brbrbrbrGetting Around:brbrCape Charles is located near the southern tip of Virginia’s Eastern Shore right on the Chesapeake Bay. Cape Charles is a small town (the historic area is roughly a six block by six block square) that sits on the peninsula’s western coast… meaning you can sit on the beach in Cape Charles and watch the sunset right over the water. On the Chesapeake Bay, not the Atlantic Ocean, the water is calm and shallow. The picturesque town of Cape Charles is filled with Americana, all about family and beautiful surroundings, voted one of the Happiest Seaside Towns by Coastal Living. Let the beach be your playground! Check out the walkable retail district, schedule a tee time at one of Bay Creek's award-winning golf courses, or take a water adventure for fishing and cruising. brbrbrbrTraveling to/around Cape Charles, Virginia: brbr• Golf Carts [i.e., Eastern Shore Custom Carts, CC Ryder Rentals]brbr• Taxi Cabs [i.e., Cape Charles Cab Cart and Carriage, Champion Cab, Rudy's Taxicab Services]brbr• STAR Transit, local fixed route and bus servicebrbr• Uber, Lyft brbr• Bike/Cycling [Rentals: Poseidon Watersports, Trek Bicycle Virginia Beach, Rent Beach Buggies]brbrbrbrAirports:brbr• Norfolk International Airport (about 45 min by vehicle)brbr• Newport News Williamsburg International Airport (PHF)brbr• Accomack County Airport (MFV)brbr• Norfolk Ns (Chambers Fld) Airport (NGU)brbr• Langley Air Force Base (LFI)brbrbrbrPopular Landmarks:brbr• Cape Charles Museum and Welcome Centerbrbr• Kiptopeke State Parkbrbr• Cape Charles Natural Area Preservebrbr• Cape Charles Lighthousebrbr• Cape Charles Town Beachbrbr• Cape Charles Brewing CompanybrbrbrbrInteraction with Guests:brbrOur goal is to make sure your stay exceeds expectations from start to finish. Portoro Homes communicates by email and phone, and once your booking is confirmed, we’ll email your rental agreement for e-signature. Check-in instructions are sent by email and text message prior to arrival, and we offer convenient self check-in. During your stay, we’ll typically check in by text once or twice to ensure a 5-star experience, and we’re available 24/7 if any questions come up. After checkout, we’ll follow up—we’re excited to hear about your stay and welcome any feedback.brbrbrbr• Early check-ins or late check-outs: Standard check-in time is 4:00 p.m. and standard check-out time is 11:00 a.m.. If the home is ready earlier on the day of arrival, an early check-in may be available with approval from our main office. Late check-outs must be requested and confirmed by the main office prior to departure.
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$405.22

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Private Vacation Home

Woody's Place on Plum - A brand new 106 year old historic property

Cape Charles, Virginia, United States

Woody's Place features high-speed internet throughout, a 70” smart tv in the living room, as well as 50 tvs in the main bedroom, and on the back porch.brbrLocated on a quiet, corner lot in the historic district, we are a short walk to everything in town. The corner lot provides for plenty of street parking (in addition to the driveway, extra space, and privacy. The front porch has two swivel chairs, while the back deck includes a large outdoor couch, 50 tv, and a large outdoor shower.brbrThe downstairs is wide open with the living room's large couch and 70 smart tv. With a comfortable half bath. The dining room has two swivel chairs, perfect for reading, a six person table, and an NBA Jam Arcade game. There is also a stackable, full size washer/dryer in the closet.brbrThe brand-new kitchen features extensive counter space, a dishwasher, and new appliances, cooking utensils, wine glasses, spices, and more. The kitchen door leads to the side entrance and the back patio, a large outdoor couch, 50 tv, outdoor shower, and barbecue grill.brbrUpstairs there are three bedrooms and another full bath with a tub. The master bedroom features a king bed and smart tv, the second bedroom has a queen, and the last bedroom has a queen bed. Each with full, walk-in closets.brbrThe house has two separate HVAC zones, with central heat and air upstairs and two mini-split units downstairs.brbrFresh linens and bath towels are provided as well.
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Exceptional(2)

$251.1

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Private Vacation Home

Beach Days & Dtwn Charm! Cape Charles Cottage

Cape Charles, Virginia, United States

Pets Welcome w/ Fee | Beach Chairs & Towels | 4 Mi to Historic DistrictbrbrSoak up the sunshine and savor vibrant small-town energy from this vacation rental in Cape Charles. The 2-bed + loft, 2-bath cottage is perfectly placed in a quiet neighborhood, inviting low-key backyard barbecues and fun-filled game nights inside. Meanwhile, you can explore the best of the Eastern Shore, from Victorian architecture in town to scenic shores at Kiptopeke State Park. Your perfect family escape starts here!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 king bedbr- Loft: 1 twin bunk bed w/ twin trundlebr- Additional Sleeping: 1 portable cribbrbrOUTDOOR LIVINGbr- Gravel patio, outdoor dining set w/ umbrellabr- Gas grill (propane provided), fire tablebr- Lounge seating, backyard (unfenced)br- Beach chairs & towelsbrbrINDOOR LIVINGbr- Smart TV, board games, children's booksbr- Dining tablebrbrKITCHENbr- Dishwasher, refrigerator, stove/oven, microwavebr- Keurig, toasterbr- Cooking basics, dishware & flatwarebr- High chair, trash bags & paper towelsbrbrGENERALbr- Central heating & A/Cbr- Towels & linens, complimentary toiletries, hair dryerbr- Washer & dryer, hangersbr- Free WiFibr- Keyless entrybrbrFAQbr- 1 exterior security camera (facing out)br- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- 2-story home, 4 steps to enterbr- Bedroom & bathroom on 1st floorbrbrPARKINGbr- Driveway (4 vehicles)br- Boat parkingbrbr-- THE LOCATION --brbr- 4 miles to downtown: fresh seafood, coffee shops, bakeries, boutiquesbr- 4 miles to Cape Charles Fishing Pier & 5 miles to Cherrystone Beach: Chesapeake Bay access br- 8 miles to Kiptopeke State Parkbr- 34 miles to First Landing State Park & Cape Henry Lighthousebr- 44 miles to Norfolk Int'l Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $50 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Must be at least 18 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story home requires 4 steps to enter, with a bedroom and full bathroom on the 1st floorbr- Your safety matters. This property features 1 exterior security camera on the front of the house facing the driveway. The camera is outward facing and does not look into interior spaces. The camera is not active while guests are in residence
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Exceptional(1)

$341.57

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Private Vacation Home

Hippie Hideaway - Tiny House w/ Fire Pit & BBQ

Cape Charles, Virginia, United States

Summary:brWelcome to Cape Charles Tiny Livin. Escape to a groovy tiny house retreat just a short drive from the beach in Cape Charles, Virginia. This unique Jimmy Hendrix themed home is filled with eccentric art and decor, making it the perfect spot for those seeking a one-of-a-kind vacation experience. brbrLounge by the fire pit, grill up a feast on the barbecue, and enjoy free WiFi and a flat-screen TV. Located just outside of town, you'll be away from the hustle and bustle but close enough to explore all that Cape Charles has to offer!brbr Bold and Beautiful: A Unique Cherry Red Tiny House brbrWelcome to our one-of-a-kind tiny house that is sure to catch your eye with its striking bright red exterior. As soon as you step inside, you'll be transported into a world of vibrant and bold design. brbrEvery inch of this tiny house has been meticulously crafted to create a unique and unforgettable experience. From the cozy seating area to the comfortable mattress, this tiny house has everything you need for a memorable stay. brbrThe interior of this charming tiny house is a vibrant and colorful space, perfectly complementing the bold red exterior. Every corner of the home is thoughtfully decorated with bright and cheerful accents, making it a truly unique and lively space. brbrFrom the playful throw pillows to the quirky wall art, this tiny house is sure to put a smile on your face. You won't find another tiny house like this one, so come and experience the bright and bold beauty for yourself.brbrbr Groove to the Beat of Our Hippie Hideaway - Jimmy Hendrix Themed Tiny House brbrLooking for a unique and eclectic vacation experience Look no further than our Jimmy Hendrix themed tiny house, the ultimate hippie hideaway! brbrFeaturing groovy decor and eccentric art, this tiny house will transport you back to the psychedelic 60s & 70s. From the bright colors to the trippy patterns, every inch of this tiny house is designed to help you unwind and let your hair down. brbrTake in the fresh air as you relax on the outdoor patio, complete with a fire pit and barbecue grills. Inside, you'll find all the amenities you need, including wifi and a flat screen TV, to stay connected while you unplug. brbrLocated just a short drive from the beach and away from the hustle and bustle of town, this tiny house is the perfect retreat for those seeking a truly unique and groovy experience. Book now and let the good vibes flow!brbrbr Gather Around the Fire & Enjoy BBQs at Our Cozy Retreat brbrImagine spending your evenings surrounded by friends and family, gathered around a crackling fire as the delicious scent of barbecue wafts through the air. brbrOur cozy retreat offers the perfect setting for you to connect with loved ones and make unforgettable memories. With a community BBQ and fire pit, you can savor delicious meals while sharing stories and creating cherished moments that will last a lifetime. The property even offers guests the chance to enjoy a fun game of cornhole with friends and family.brbrWhether you're roasting marshmallows or grilling up your favorite dishes, our outdoor space is the ideal place to unwind and enjoy the peaceful serenity of nature. Don't miss out on this unique opportunity to experience the ultimate in relaxation and rejuvenation.brbrbr Unbeatable Amenities for Your One-of-a-Kind Getaway brbr Pamper yourself with our complimentary hair dryer, shampoo, and Ginger Lilly body soap.br Enjoy a hot shower anytime with our reliable hot water and shower gel provided for your convenience.br Relax in comfort with our quality bedroom and laundry essentials, including towels, bed sheets, soap, and toilet paper.br Keep your clothes neat and organized with our hangers and bed linens, and enjoy a good night's sleep with our room-darkening shades.br Look your best with our iron provided in the unit.br Stay entertained with our TV featuring Roku for your favorite shows and movies.br Stay cool in the summer with our window AC unit, and cozy in the winter with our heating system.br Stay safe with our security cameras located outside the property, and our smoke alarm, carbon monoxide alarm, fire extinguisher, and first aid kit provided in the unit.br Stay connected with our high-speed Wifi, verified by speed test, and suitable for streaming 4K videos and joining video calls.br Satisfy your hunger and thirst with our microwave, mini fridge, coffee maker, wine glasses, and coffee provided in the unit.br Soak up the sun and fresh air in our private patio, backyard, and outdoor furniture.br Gather around our fire pit, and enjoy a meal with our outdoor dining area and BBQ grill.br Park your car for free on our premises, and enjoy the convenience of our single level home with no stairs.br Enjoy a hassle-free check-in with our self-check-in and smart lock system.brbrbr Coastal Tiny House Just Minutes from the Beach brbrEscape the crowds and unwind at our secluded coastal retreat in Cape Charles, Virginia. Located just a short drive from the beach, you can soak up the sun and feel the sand between your toes in no time. brbrAnd when you're ready to relax and recharge, our peaceful location just outside of town offers the perfect respite from the hustle and bustle of everyday life. Enjoy the best of both worlds - easy access to all the area has to offer, combined with the privacy and tranquility you crave. brbrBook your stay today and start making unforgettable memories at our hidden gem by the sea.brbrGuests will have full and private access to the entire tiny house and its outdoor amenities, including the fire pit, barbecue grills, and outdoor dining area. The house features a private entrance, and there are no shared spaces with other guests or hosts.brbrSelf check-in is available with a smart lock, so guests can arrive at their convenience without worrying about coordinating with a host. The lock uses a unique code for each guest, ensuring that only those with authorized access can enter the property.brbrThe house is equipped with high-speed Wi-Fi, and guests can enjoy streaming movies or working remotely from the comfort of their own space.brbrFor added convenience, we provide all essential amenities, including clean towels, bed sheets, soap, shampoo, and toilet paper. Additionally, we offer a mini fridge, coffee maker, and microwave for guests to prepare simple meals or snacks during their stay.brbrWith no stairs in the home, the single-level layout is easily accessible for all guests. And, for those traveling by car, free parking is available on the premises.brbrOur goal is to provide a comfortable and convenient home away from home for our guests, so they can relax and enjoy all that Cape Charles has to offer.
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Exceptional(7)

$635.4

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Private Vacation Home

The Great Escape | Downtown Cape Charles Walk to Shops & Dining, Restored 5BR Retreat

Cape Charles, Virginia, United States

Discover the charm of Cape Charles in this beautifully restored 5-bedroom, 3-bathroom house, available for your next vacation adventure. Nestled in the heart of downtown, The Great Escape places you just minutes away from a vibrant selection of shopping, dining, and entertainment options, including local ice cream shops and mini-golf. Whether you're enjoying the bustling town scene or relaxing at home, this property offers both convenience and comfort.brbrStep onto the inviting open front porch where you can sip your morning coffee while soaking in the town views. Alternatively, the screened porch provides a tranquil retreat to unwind in the evenings without the pesky insects. Inside, you'll find a clean and comfortable interior with ample living space that caters to both large and small families alike.brbrThe Great Escape is ideal for those seeking a blend of small-town charm and modern amenities, all within walking distance of Cape Charles' delightful attractions. Whether you're settling down with your family or looking for a scenic change of pace, this vacation home promises a lifestyle of ease and excitement. Don't miss out on making this house your new home away from home — book your getaway today!brbr- Linens and towels are included with your reservation. br- No smoking is permitted on the premises. br- No pets are permitted on the premises. br- Any reservations made for a future year (known as Advanced Reservations) are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.
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Exceptional(4)

$990.27

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Private Vacation Home

Sunset on the Rocks | 4BR Bayview Butler's Bluff Retreat w/ Game Room + Pet Friendly

Cape Charles, Virginia, United States

Experience coastal living at its finest in this stunning 4-bedroom, 3.5-bathroom abode nestled within the prestigious Butler's Bluff community of Cape Charles, VA. Boasting an impressive 4,900 sq ft of interior space, this home offers a perfect blend of luxury, fun and comfort.brbrThe heart of this home lies in its expansive windows that frame mesmerizing views of the Chesapeake Bay. The interiors are thoughtfully designed to maximize both comfort and elegance, featuring a dedicated game room and a serene lookout sitting area ideal for enjoying breathtaking sunsets or a quiet morning coffee.brbrOutdoors, the property exhibits meticulously maintained landscaping that harmonizes with its secluded setting. Entertain or simply unwind in the outdoor seating areas that provide a private beach feel without leaving your home. The charm of this residence is enhanced by its proximity to downtown Cape Charles, where you can indulge in local restaurants, eclectic shops, tasty ice cream parlors, and entertaining mini-golf options, all just minutes away.brbrPet owners will appreciate the pet-friendly environment, ensuring every family member is catered for in this idyllic locale.brbrThis home not only promises a peaceful and picturesque setting but also offers practicality with its generous room sizes and versatile living spaces. Whether it's hosting gatherings, family game nights, or simply enjoying the solace of the bay, this escape provides the perfect setting.brbr- Linens and towels are included with your reservationbr- No smoking is permitted on the premises. br- This home is pet friendly (with fee). Maximum of two dogs; no cats.br- Any reservations made for a future year (known as Advanced Reservations) are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.
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$365.91

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Shore Reflections | Restored Victorian Retreat Near Cape Charles, Spacious & Charming

Cape Charles, Virginia, United States

Now available and awaiting your next vacation adventure, this lovingly restored 4-bedroom Victorian home blends traditional charm with modern convenience. Nestled in a picturesque setting with beautiful landscaping and mature trees, you're just a 10-minute drive from the vibrant Cape Charles community. Explore and enjoy downtown Cape Charles, which features a pristine beach, delicious food offerings, eclectic shopping, ice cream treats, coffee shops and so much more!brbrSpanning 3,000 sq ft, this exquisite property features a layout with high ceilings and wood flooring throughout, enhancing the airy and expansive feel of each room. The main living spaces boast large windows that flood the home with natural light, creating a warm, welcoming atmosphere. Four generously sized bedrooms offer ample personal space for relaxation and rejuvenation. The home also includes 2.5 bathrooms, each maintaining the character of the house with tasteful touches.brbrGuests will enjoy a beautifully landscaped yard, ideal for leisurely days spent outdoors or entertaining guests in a serene environment. The kitchen, equipped with essential appliances, provides a comfortable space for culinary exploration and seamlessly caters to both casual dining and larger gatherings.brbrThis property is perfect for those who appreciate the beauty of historic homes but expect the functionality needed for a contemporary lifestyle. Make your home away from home in a place where tradition meets comfort in the heart of Eastville, VA. Experience the unique charm of this Victorian beauty and the inviting community that surrounds it.brbr- No smoking is permitted on the premises. br- Linens and towels are provided for your stay. br- No pets are permitted on the premises.br- Any reservations made for a future year (known as Advanced Reservations) are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.
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Exceptional(56)

$364.48

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Across from the park and 2 blocks from beach & restaurants- LEFT side of duplex

Cape Charles, Virginia, United States

Perfect for families with children; And for Two Families to Rent Side-by-side!brWe offer BOTH mirror image sides of our vacation rental duplex, 303 and 305 Strawberry Street. We recently purchased this duplex and plan to continue the history of making memories for families for years to come! This 1925 duplex has beautiful soft light from tall windows and a great dining room to gather. Couples, small groups of friends, and families who want to slow down, go to the beach and the park, and relax in this walk-able small town should feel right at home.brbrEach side has 3 bedrooms and 1.5 baths - they are similar bot not identical. The atmosphere is sunny coastal with style-conscious kitchen and baths. The property has a fenced-in small yard with deck with table and 4 chairs, upscale grill, outdoor shower, and some beach gear for your convenience.brbrOur property is conveniently located at the crossroads of Cape Charles - an easy walk to downtown, the beach, and across the street from Central Park. The duplex has a covered porch to enjoy your coffee in the morning overlooking the park and a back deck with table/chairs, umbrella and new gas grill, overlooking the fenced-in back yard with outdoor shower. The kitchen is newly equipped with upscale dishes and serving pieces if you like to entertain, Keurig coffee maker, electric and stovetop teapots. The kitchen also has a high chair, or youth chair if the tray is removed, plus children's dishes are provided.brbrWiFi internet is provided and a new 40 flat screen. We've added a few DVDs, games, and books in the dining room bookshelf, along with a few toys/puzzles. brbrBedrooms: 1 with a king size bed, 1 with a double bed and 1 with 2 twin-size beds. Linens provided by a linen service.brbrThere is an outdoor shower and small, fenced-in back yard. Beach gear that is provided to lighten the load of your travel here includes: 4 beach chairs and beach cart. Sometimes guests have left their purchases, e.g., fishing poles and crab nets, rather than take them home. There is a stacking washer-dryer in the kitchen. For dog(s) approved in advance, dog bed is provided. A pet cleaning fee is charged for approved dogs. An additional cost of cleaning any furniture and bed spreads will be retained from your security deposit if the fur is found on the furniture and beds.brbrCape Charles is embraced by water on three sides: commercial town harbor and yacht center (south), public beach (west), and marina (north). It's a wonderful setting if you love the water! Park Place is 3 blocks from the beach (Bay Ave.) and 2 blocks from the shops on main street (Mason Ave.). We are a mile from Bay Creek's two signature golf courses by Arnold Palmer and Jack Nicklaus, with top ratings by Golf Digest. The area promotes eco-tourism opportunities, including kayaking (even kayak/wine-tasting trips to a local winery), fishing off the town pier, hiking, and birding. You can rent jet skis at the harbor, bicycles, and golf carts. The town often has festivals, planned recreational activities for children and adults, and sometimes shows, movies, or live bands in the Park. The Eastern Shore Birding and Wildlife Festival in early October - fall weather is great here! Festive Fridays for shopping and Christmas treats are held the month of December on Mason Avenue. Year-round, Cape Charles has live theater performed by Arts Enter and others at the Palace Theater, art galleries, a Brown Dog ice cream shop, ladies upscale consignment, and beautiful spa to name a few of the attractions in town! We have good eateries and, if you like nostalgia, be sure to stop by the lunch counter at Rayfield's pharmacy at the corner of Mason Ave. and Fig. Street. Cape Charles Medical Center is located on Mason Ave. too. brbrbrbr
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Exceptional(55)

$827.75

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2 Blocks to beach, Dog Friendly, Fenced Yard, Firepit, Fireplace,Renovated

Cape Charles, Virginia, United States

Renovated, Historic home, located in downtown Cape Charles . Walk the 2 blocks to the Beach each morning, and evening to see the sun set over the horizon. This dog friendly home offers a great way to explore cape Charles and have fun each day at the beach. The fenced in back yard, offers privacy and a place for the dogs to play without worry. brThe home offers a propane fireplace in the living room, and a main level bedroom with a King bed and private bathroom. Fireplace is on Oct 1st to May 1st only. Do not use when a/c is on.brLots of parking out back -3 cars, so you aren't on the street. Entry thru backyard, with gate . You can park one or 2 cars out front , on the street. Enter thru back gate and backyard.brbrYou must plug in your golf cart out back also, cord/plug runs along the fence now, yet you still need a 20 foot cord, they do have them at the rental places. Please Do not drive on the front lawn at all, with golf carts or anything, this is very expensive to repair and is not fair to the next guest, to have yard crew digging it up to replace it. Please note NO EV charging , at this home, even with regular plug, due to fire hazards . There is an EV station on Mason that you can go to .brbrDesk, with printer/ copier / scanner and fast wifi. The new furniture, renovations and new kitchen/baths with fresh paint are a welcoming site. New windows and doors, 2023, when it is not so hot or cold and you desire to open. New furniture, mattresses and more , 2022 and each year upgrading. 2024, new water lines, so water quality here is better than other homes.. Painted each year to help with inside when baggage hits those wallsbrbrHave fun in the firepit or the deck in the backyard . One area of sand and another of grass compliment the yard, with both sun and shade. Propane grill and picnic table as well. Fig trees, please eat, before the birds do. Rosemary, mint , basil , lavender and more are grown for your use. Some herbs may not be available, but lavender and mint are year round, and help control flies/mosquitos. brbrPrivacy trees with lots of shade , for those pups and small ones.. Sun as well, but you have room to sit in the shade or the sun in the summer. brbrHome is located with the library behind it and Browns Ice Cream, ( this could be a great thing or a calamity, if your are trying to limit intake ) . You can walk to everything in the town from this home , even the Shanty Restaurant. Cape Charles offers music in the park or in town, each week with a different concert, in the summer ! Have fun with the locals and your family. Tennis courts in downtown Cape Charles in the park. December is beautiful with festivals each weekend in town. brbrFestive Fridays in December, starting Thanksgiving weekend- each Friday is a different theme. Come celebrate and shop with Mason Ave shut down , parades, music, Santa and more . Just walk out the back yard here and you will be in the middle of the festival ! brbrDogs allowed any size, and let us know quantity please. Fee per dog. Please note, dogs allowed before 9am on the beach from May to Labor Day. During the shoulder season, and winter , they can go all day, currently. Please pick up after your dog ,so we can remain dog friendly .brbrPlease note: no events allowed or parties. The home is licensed for 9 occupants as per local and county laws total, children 3 and under are not counted. brbrThis home has actually been dated back to 1800 to 1830, due to an old window, in the sunroom now, and the side windows near the front door. If that breaks-we discovered we have to order the glass out of Belgium currently. The glass dates to the Jeffersonian glass from his factory in Richmond that burned down in the 1830's .. and how do I know this As an architect with the AIA, I have had the historical chapters analyze the glass, trusses and more of the home . I work on the home slowly with experts. It is critical to preserve this home, it is one of the originals in town. The foundation was worked on 2023, so the floors are level now, the staircase yes is steep, however, no one can correct this without tearing down the home. As an architect and preservationist, this is one of those wonderful qualities of a home from 1800 to 1830. This home was built before the town was established. brIt is a great home, and I know the owner that grew up in this home , one of the original Cape Charles people left today. ( yes they grew up in the home in the 1940's on ). Their value added is wonderful, so we could take the home back correctly and understand the nuances.brbrPlease note, there are flies, fruit flies, mosquitos, and perhaps some other insects flying in the yards and they do get in the homes, due to weather, surrounding area, and beach. The fig trees attract alot of these. We do have Terminix to assist with this control of these flies, outside and inside. They also offer a natural product. There are no refunds for flies/ fruit flies or any flying insect, we cannot control nature . These come every year- just use the replacement filters for the plug ins that are in the home, to assist with any entries. br Best to cook all crab outside as well, since this also leaves an odor and attracts lots of flies.
Bed 4

Bed

Bath 3

Bath

Sleep 9

Sleeps

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Exceptional(12)

$669.78

/ Nightly
Private Vacation Home

Anchors Aweigh

Cape Charles, Virginia, United States

Anchors Aweigh was originally built in 1894 and has recently undergone extensive renovations to create a home of charm, history, and comfort. Located a block away from Mason Avenue, three blocks from beach, two blocks from Cape Charles's Central Park, Anchors Aweigh is in a prime location in Cape Charles.brbrAnchors Aweigh is a historic home in Cape Charles originally built in 1894 and consists of four bedrooms and two and a half baths. There are five beds and one futon with a pull-out bed to sleep up to nine guests total comfortably. On the third floor, there is a bedroom with a king-size bed and a full bath. On the second floor, there are three bedrooms with a full bathroom including a soaking tub. There are two queen beds and two twin beds. On the first floor, there is a media room next off of the hallway and has a pull-out futon bed to accommodate an additional guest. Each bedroom also has its own TV available for streaming and ample bedroom storage during your stay. Towels, shower essentials, and a hairdryer will be provided during your stay. brbrDownstairs there is a living room, dining room and kitchen. In the living room, there is a Smart TV to stream your favorite shows and movies as well as a built-in cabinet bar to enjoy a drink with friends and family. The bar will be equipped with a cocktail maker set, glasses, and an ice bucket. The kitchen is outfitted with brand-new stainless steel appliances, granite countertops, and a kitchen island with four barstools. The kitchen has all your essentials including a Keurig, hot water kettle, toaster, pots, pans, utensils, spices, plates, and drinkware. Off the kitchen, there is a mudroom that has a washer and dryer, and beach essentials including beach towels. brbrIn the backyard, there is a beautiful new patio, dining, firepit, and grill all under the outdoor cafe lights. The backyard also features a cornhole game for enjoyment. Please note the backyard is unfenced. Off the backyard, there is an outdoor shower to rinse off after visiting the beach and an outdoor bin with the beach chairs and umbrella. The front of the house has a front porch with ceiling fans to enjoy coffee or tea in the morning. brbrAnchors Aweigh is centrally-located and ready to host your next stay in the small beach town of Cape Charles, VA.brbrParking is available next to the home. The driveway fits 1 car and/or a golf cart rental. There is a plug on the side of the home next to the driveway to charge golf cart batteries. There is also free street parking in front of the home. Cape Charles is easily accessible via walking, driving, or renting a golf cart.brbrDuring the off-season (October-April), the Anchors Aweigh offers discounted stays when you book for 28 nights or more - perfect for remote workers, travel nurses, or anyone looking for an extended stay on the Eastern Shore!
Bed 5

Bed

Bath 2

Bath

Sleep 10

Sleeps

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Exceptional(6)

$387.72

/ Nightly
Private Vacation Home

Flip Flop Cottage - Chesapeake Properties

Cape Charles, Virginia, United States

Summary:brbrPet-Friendly 2-Bedroom Cottage in Cape Charles, VA, Offers Beachside Bliss!brbrbrbrPlease SEE: Other Things to NotebrbrFor Area Details, Please SEE: The Neighborhood & Getting Aroundbrbr*Pet Friendly, fee applies per pet.brbrbrbrThe Space:brbrFlip Flop Cottage, Home Features:brbr• 2 Bedroom, 1.5 Bath - Available for up to 6 Guests!brbr• Beachy Decor & Natural Lightingbrbr• Fully Equipped Kitchenbrbr• Open Front Porch with Seatingbrbr• Free WiFi & Smart TVsbrbrbrbrNestled in the charming beach town of Cape Charles, Virginia, this delightful 2-bedroom cottage offers the perfect retreat for those seeking sun, sand, and relaxation. Bring along your furry friends, as this pet-friendly rental welcomes them with open arms.brbrbrbrStep inside to discover a cozy living space adorned with beachy decor and plenty of natural light. The fully equipped kitchen invites you to whip up delicious meals, while the dining area provides a setting for enjoying them together.brbrbrbrWith two comfy bedrooms, and a sleeper sofa in the living room, this cottage accommodates up to six guests. After a day of beachcombing and exploration, unwind on the open front porch with a cool drink or gather around the outdoor side patio for cozy evenings under the stars.brbrbrbrLocated just a short stroll from the pristine shores of Cape Charles Beach, this cottage is ideally situated for endless days of bayside fun. Explore the charming shops and restaurants of downtown Cape Charles, or embark on a scenic nature hike at Kiptopeke State Park.brbrbrbrWhether you're seeking adventure or simply craving a peaceful escape, this pet-friendly cottage in Cape Charles promises an unforgettable vacation experience. Book your stay today and start counting down the days until beachside bliss!brbrbrbrGuest Access:brbrWe offer convenient door codes for self-check-in. Chesapeake Properties by Portoro uses convenient keyless entry for self check-in, details provided 2 weeks (or less) prior to arrival by email and text message.brbrbrbr• Early check-ins or late check-outs: If the property happens to be ready earlier than the standard 4 pm check-in time on the day of your arrival, in most cases an early arrival option may be available when confirmed with the main office. Late check-outs must be confirmed with main office staff prior to the date of departure.brbrbrbrThe Neighborhood:brbrNoted on the National Register of Historic Places, Northampton County's Cape Charles offers one of the largest concentrations of turn-of-the-century buildings on the East Coast. The historic district and small-town atmosphere create a serene and inviting community. Enjoy the history and experience galleries, boutiques, bookshops, and beautiful beach! Cape Charles Town Beach is the only free public beach on the Easter Shore of Virginia.brbrbrbrThings to See:brbr• Local Experiences: Take a Boat Tour, Kiteboarding, Kayaking, Paddleboarding, Explore the Beach, Fishing, Golf, Hiking, Biking, Birding & More!brbr• Local Restaurants & Shoppingbrbr- Restaurants: The Shanty, Oyster Farm Seafood Eatery, Kelly's Gingernut Pub, Pane e Vino, Ambrogia Caffe & Enoteca, Cravings, Beach Marketbrbr- Shops: The Boardwalk, Table and Tonic Cape Charles, Cape Charles Candy Company, Love Letters, Gull Hummock Gourmet Market, Chessie's Toys and Games & more!brbrbrbrAnnual Festivals & Events:brbr• Crabby Blues Festivalbrbr• Annual Crab Slambrbr• LOVEFestbrbr• Sounds of the Shorebrbr• Festive Fridays, Cape Charles Winter Wonderland (Nov-Dec)brbr• Free Concert in the Park (Summer Season)brbr• Grand Illumination (Dec)brbrbrbrWe provide a full list of Things to Do & See and local Restaurants & Shops to experience for our guests including in a personalized Guest Manual in your check-in details provided prior to your stay!brbrbrbrGetting Around:brbrCape Charles is located near the southern tip of Virginia’s Eastern Shore right on the Chesapeake Bay. Cape Charles is a small town (the historic area is roughly a six block by six block square) that sits on the peninsula’s western coast… meaning you can sit on the beach in Cape Charles and watch the sunset right over the water. On the Chesapeake Bay, not the Atlantic Ocean, the water is calm and shallow. The picturesque town of Cape Charles is filled with Americana, all about family and beautiful surroundings, voted one of the Happiest Seaside Towns by Coastal Living. Let the beach be your playground! Check out the walkable retail district, schedule a tee time at one of Bay Creek's award-winning golf courses, or take a water adventure for fishing and cruising.brbrbrbrTraveling to/around Cape Charles, Virginia:brbr• Taxi Cabs [i.e., Cape Charles Cab Cart and Carriage, Champion Cab, Rudy's Taxicab Services]brbr• STAR Transit, local fixed route and bus servicebrbr• Uber, Lyftbrbr• Bike/Cycling [Rentals: Poseidon Watersports, Trek Bicycle Virginia Beach, Rent Beach Buggies]brbrbrbrAirports:brbr• Norfolk International Airport (about 45 min by vehicle)brbr• Newport News Williamsburg International Airport (PHF)brbr• Accomack County Airport (MFV)brbr• Norfolk Ns (Chambers Fld) Airport (NGU)brbr• Langley Air Force Base (LFI)brbrbrbrPopular Landmarks:brbr• Cape Charles Museum and Welcome Centerbrbr• Kiptopeke State Parkbrbr• Cape Charles Natural Area Preservebrbr• Cape Charles Lighthousebrbr• Cape Charles Town Beachbrbr• Cape Charles Brewing CompanybrbrbrbrOther Things to Note:brbrPlease pay close attention to following the house rules. Non compliance could result in sizable fines.brbr- All guests staying at an Chesapeake Properties Vacation Rentals by Portoro (Portoro Homes) are required to sign (esignature) a rental agreement and complete identity registration.brbr- Age restrictions apply. Reservation holder must be 25 years of age.brbr- Upon arrival, we aim to ensure your safety, proper access to the home, and guest features. Should you have any questions, please don't hesitate to reach out to Chesapeake Properties by Portoro directly. brbr- Known damages incurred during your stay must be reported to the property manager immediately. brbr- Before check in, we will send you detailed directions to ensure a seamless arrival.brbr- Check-in time is 4:00 p.m. Check-out time is 10:00 a.m.brbr- We cannot guarantee early check ins or late checkouts. When it is possible to check in early or check out late, there will be a fee for anything outside of a one hour window within our standard times. If your need for an early check in or late check out is great, your best option is to book an additional night.brbr- Some homes have cameras for external monitoring only.brbr- HOTEL TAX COLLECTION: In the State of Virginia and in Northampton County, all hotel and vacation rental hosts are required to collect hotel tax. We collect these taxes within the booking transaction. brbr- Some homes offer pools/hot tubs, or access to communal pools. There is no guard around the water features when available. Use at your own risk.brbr- This is a No Smoking property. Penalty fees for violations will apply and you may be asked to vacate the premises with no refund at the discretion of the Host.brbrbrbr- Animals/Pets -- Dogs Only, Guidelines and Fee*brbrAnimals/pets must be disclosed prior to reservation arrival date. Only dogs are permitted in “Pet-Friendly” Property listings. Allowed number of dogs will be expressly stated in the listing and a $150.00 fee per animal/pet is required. Animals/pets are not permitted anywhere on the premises unless prior approval is obtained. Any unauthorized animals/pets at the property will result in a $150.00 per day / per animal/pet fee, and may result in your reservation being canceled, and you may be required to vacate from the Property. brbr-- The property allows for a maximum of 2 dogs at $150.00 per dog per stay.brbr- For the safety of guests and the home, there are noise monitoring devices. These devices only measure the decibel level and do NOT record any audio.brbrbrbrInteraction with Guests:brbrOur goal is that your vacation exceed your expectations. Chesapeake Properties by Portoro communicates via email and phone. After a booking is confirmed, rental agreement will be emailed to the guest for e-signature. Check-in instructions are sent by email and text message 14 days (or less) prior to arrival date. We offer convenient keyless entry for self-check in. We do typically check in with guests by text 1-2 times during their stays to ensure a 5-star experience and remain available for any questions. We are available to guests 24/7 for any inquiries.
Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps

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Exceptional(2)

$521.68

/ Nightly
Private Vacation Home

Nautical Miles - Chesapeake Properties

Cape Charles, Virginia, United States

Summary:brNewly Renovated: Unveiling Cape Charles, VA's Latest Vacation Rental Gem! New appliances, furniture and bedding! And the owner is continuously improving this new rental!! Adding new photos as we go along!brbrPlease SEE: Other Things to NotebrFor Area Details, Please SEE: Where You'll Be (Located under the map!)br*Pet Friendly, fee applies per pet.brbrThe Space:brNautical Miles, Home Features:br• 3 Bedroom, 2 Bath - Available for up to 9 Guests!br• Fully Equipped Kitchen, Stainless Steel Appliancesbr• TV Room with Board Gamesbr• Private Backyard Patio & Grillbr• Free WiFi & Smart TVsbrbrEscape to the tranquil shores of Cape Charles, VA, and indulge in a coastal getaway unlike any other! Nestled in this charming beach town, our newly renovated 3-bedroom, 2-bath ranch offers the perfect retreat for families, friends, and couples seeking relaxation and adventure.brbrStep inside to discover a beautifully appointed interior, blending modern comforts with beach-inspired décor. The spacious living area invites you to unwind with plush furnishings and abundant natural light streaming through the many windows. Kick back and catch up on your favorite shows on the flat-screen TV or gather and play board games with loved ones.brbrPrepare delicious meals in the fully equipped kitchen, featuring sleek countertops, stainless steel appliances, and ample cabinet space for all your culinary essentials. Enjoy meals together in the adjacent dining area, where sliding glass doors lead to a private outdoor patio.brbrWhen it's time to rest, retreat to one of three inviting bedrooms, each thoughtfully designed to ensure a peaceful night's sleep. The master suite boasts a luxurious king bed and en-suite bath, complete with a walk-in shower and elegant vanity. Two additional bedrooms offer comfortable accommodations for guests, with a queen beds & bunk room detailed with charming coastal accents.brbrOutside, you'll find your own private oasis awaiting. Relax on the spacious patio and soak up the sunshine, or fire up the grill for a delightful barbecue with friends and family. Afterward, gather around the picnic table and stargazing under the clear night sky.brbrWith the beach just moments away, endless adventures await! Spend your days swimming, sunbathing, and building sandcastles along the pristine shoreline, or explore the town's vibrant shops, restaurants, and attractions. Embark on a scenic bike ride along the nearby trails, or relax in the sun room addition with a good book.brbrWhether you're seeking relaxation or excitement, our charming ranch provides the perfect home base for your Cape Charles retreat. Book your stay today and start making memories that will last a lifetime!brbrGuest Access:brWe offer convenient door codes for self-check-in. Chesapeake Properties by Portoro uses convenient keyless entry for self check-in, details provided 2 weeks (or less) prior to arrival by email and text message.brbr• Early check-ins or late check-outs: If the property happens to be ready earlier than the standard 4 pm check-in time on the day of your arrival, in most cases an early arrival option may be available when confirmed with the main office. Late check-outs must be confirmed with main office staff prior to the date of departure.brbrThe Neighborhood:brMost who visit fall in love within a few minutes! Noted on the National Register of Historic Places, Northampton County's Cape Charles offers one of the largest concentrations of turn-of-the-century buildings on the East Coast. The historic district and small-town atmosphere create a serene and inviting community. Enjoy the history and experience galleries, boutiques, bookshops, and beautiful beach! Cape Charles Town Beach is the only free public beach on the Easter Shore of Virginia.brbrThings to See:br• Local Experiences: Take a Boat Tour, Kiteboarding, Kayaking, Paddleboarding, Explore the Beach, Fishing, Golf, Hiking, Biking, Birding & More!br• Local Restaurants & Shoppingbr- Restaurants: The Shanty, Oyster Farm Seafood Eatery, Kelly's Gingernut Pub, Pane e Vino, Ambrogia Caffe & Enoteca, Cravings, Beach Marketbr- Shops: The Boardwalk, Table and Tonic Cape Charles, Cape Charles Candy Company, Love Letters, Gull Hummock Gourmet Market, Chessie's Toys and Games & more!brbrAnnual Festivals & Events:br• Crabby Blues Festivalbr• Annual Crab Slambr• LOVEFestbr• Sounds of the Shorebr• Festive Fridays, Cape Charles Winter Wonderland (Nov-Dec)br• Free Concert in the Park (Summer Season)br• Grand Illumination (Dec)brbrWe provide a full list of Things to Do & See and local Restaurants & Shops to experience for our guests including in a personalized Guest Manual in your check-in details provided prior to your stay!brbrNorthampton County Short-Term Rental Registration No. #brbrGetting Around:brCape Charles is located near the southern tip of Virginia’s Eastern Shore right on the Chesapeake Bay. Cape Charles is a small town (the historic area is roughly a six block by six block square) that sits on the peninsula’s western coast… meaning you can sit on the beach in Cape Charles and watch the sunset right over the water. On the Chesapeake Bay, not the Atlantic Ocean, the water is calm and shallow. The picturesque town of Cape Charles is filled with Americana, all about family and beautiful surroundings, voted one of the Happiest Seaside Towns by Coastal Living. Let the beach be your playground! Check out the walkable retail district, schedule a tee time at one of Bay Creek's award-winning golf courses, or take a water adventure for fishing and cruising.brbrTraveling to/around Cape Charles, Virginia:br• Taxi Cabs [i.e., Cape Charles Cab Cart and Carriage, Champion Cab, Rudy's Taxicab Services]br• STAR Transit, local fixed route and bus servicebr• Uber, Lyftbr• Bike/Cycling [Rentals: Poseidon Watersports, Trek Bicycle Virginia Beach, Rent Beach Buggies]brbrAirports:br• Norfolk International Airport (about 45 min by vehicle)br• Newport News Williamsburg International Airport (PHF)br• Accomack County Airport (MFV)br• Norfolk Ns (Chambers Fld) Airport (NGU)br• Langley Air Force Base (LFI)brbrPopular Landmarks:br• Cape Charles Museum and Welcome Centerbr• Kiptopeke State Parkbr• Cape Charles Natural Area Preservebr• Cape Charles Lighthousebr• Cape Charles Town Beachbr• Cape Charles Brewing CompanybrbrOther Things to Note:brPlease pay close attention to following the house rules. Non compliance could result in sizable fines.br- All guests staying at an Chesapeake Properties Vacation Rentals by Portoro (Portoro Homes) are required to sign (esignature) a rental agreement and complete identity registration.br- Age restrictions apply. Reservation holder must be 25 years of age.br- Upon arrival, we aim to ensure your safety, proper access to the home, and guest features. Should you have any questions, please don't hesitate to reach out to Chesapeake Properties by Portoro directly. br- Known damages incurred during your stay must be reported to the property manager immediately. br- Before check in, we will send you detailed directions to ensure a seamless arrival.br- Check-in time is 4:00 p.m. Check-out time is 10:00 a.m.br- We cannot guarantee early check ins or late checkouts. When it is possible to check in early or check out late, there will be a fee for anything outside of a one hour window within our standard times. If your need for an early check in or late check out is great, your best option is to book an additional night.br- Some homes have cameras for external monitoring only.br- HOTEL TAX COLLECTION: In the State of Virginia and in Northampton County, all hotel and vacation rental hosts are required to collect hotel tax. We collect these taxes within the booking transaction. br- Some homes offer pools/hot tubs, or access to communal pools. There is no guard around the water features when available. Use at your own risk.br- This is a No Smoking property. Penalty fees for violations will apply and you may be asked to vacate the premises with no refund at the discretion of the Host.brbr- Animals/Pets -- Dogs Only, Guidelines and Fee*brAnimals/pets must be disclosed prior to reservation arrival date. Only dogs are permitted in “Pet-Friendly” Property listings. Allowed number of dogs will be expressly stated in the listing and a $150.00 fee per animal/pet is required. Animals/pets are not permitted anywhere on the premises unless prior approval is obtained. Any unauthorized animals/pets at the property will result in a $150.00 per day / per animal/pet fee, and may result in your reservation being canceled, and you may be required to vacate from the Property. br-- The property allows for a maximum of 2 dogs at $150.00 per dog per stay.br- For the safety of guests and the home, there are noise monitoring devices. These devices only measure the decibel level and do NOT record any audio.brbrInteraction with Guests:brOur goal is that your vacation exceed your expectations. Chesapeake Properties by Portoro communicates via email and phone. After a booking is confirmed, rental agreement will be emailed to the guest for e-signature. Check-in instructions are sent by email and text message 14 days (or less) prior to arrival date. We offer convenient keyless entry for self-check in. We do typically check in with guests by text 1-2 times during their stays to ensure a 5-star experience and remain available for any questions. We are available to guests 24/7 for any inquiries.
Bed 3

Bed

Bath 2

Bath

Sleep 9

Sleeps

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Exceptional(6)

$368.5

/ Nightly
Private Vacation Home

The Madison Suite - Chesapeake Properties

Cape Charles, Virginia, United States

Summary:brbrNEW! The new cottage on the block! This newly renovated 1 bedroom cottage is nestled just 1 and a half blocks from the beach!brbrbrbrPlease SEE: Other Things to NotebrbrFor Area Details, Please SEE: Where You'll Be (Located under the map!)brbr*This is a no pet/animal home.brbrbrbrThe Space:brbrThe Madison Suite, Home Features:brbr• 1 Bedroom, 1 Bath - Available for up to 2 Guests!brbr• Just 1.5 Blocks from the Beach!brbr• Well-Equipped Kitchen & Stainless Steel Appliancesbrbr• Close to the Town's Central Park & Downtownbrbr• Free WiFi & Smart TVsbrbrbrbrNew to the rental program and newly renovated cottage just 1.5 blocks from the beach! This home is ideal for a couple's romantic beach getaway for 2! This home has 1 bedroom with a queen bed and 1 full bathroom with a tub/shower combo with new tile surround. The kitchen is well-appointed with new stainless steel appliances, the dining room has a dining table that seats 6, and a large backyard with an outdoor shower and gas grill. The house is close to the town's central park and downtown! What more can you ask for brbrbrbrThe laundry room with a full-sized washer and dryer is attached to the house but is only accessible from the outside.brbrbrbr**No pets allowed at this property**brbrbrbrGuest Access:brbrWe offer convenient door codes for self-check-in. Chesapeake Properties by Portoro uses convenient keyless entry for self check-in, details provided 2 weeks (or less) prior to arrival by email and text message.brbrbrbr• Early check-ins or late check-outs: If the property happens to be ready earlier than the standard 4 pm check-in time on the day of your arrival, in most cases an early arrival option may be available when confirmed with the main office. Late check-outs must be confirmed with main office staff prior to the date of departure.brbrbrbrThe Neighborhood:brbrNoted on the National Register of Historic Places, Northampton County's Cape Charles offers one of the largest concentrations of turn-of-the-century buildings on the East Coast. The historic district and small-town atmosphere create a serene and inviting community. Enjoy the history and experience galleries, boutiques, bookshops, and beautiful beach! Cape Charles Town Beach is the only free public beach on the Easter Shore of Virginia.brbrbrbrThings to See:brbr• Local Experiences: Take a Boat Tour, Kiteboarding, Kayaking, Paddleboarding, Explore the Beach, Fishing, Golf, Hiking, Biking, Birding & More!brbr• Local Restaurants & Shoppingbrbr- Restaurants: The Shanty, Oyster Farm Seafood Eatery, Kelly's Gingernut Pub, Pane e Vino, Ambrogia Caffe & Enoteca, Cravings, Beach Marketbrbr- Shops: The Boardwalk, Table and Tonic Cape Charles, Cape Charles Candy Company, Love Letters, Gull Hummock Gourmet Market, Chessie's Toys and Games & more!brbrbrbrAnnual Festivals & Events:brbr• Crabby Blues Festivalbrbr• Annual Crab Slambrbr• LOVEFestbrbr• Sounds of the Shorebrbr• Festive Fridays, Cape Charles Winter Wonderland (Nov-Dec)brbr• Free Concert in the Park (Summer Season)brbr• Grand Illumination (Dec)brbrbrbrWe provide a full list of Things to Do & See and local Restaurants & Shops to experience for our guests including in a personalized Guest Manual in your check-in details provided prior to your stay!brbrbrbrGetting Around:brbrCape Charles is located near the southern tip of Virginia’s Eastern Shore right on the Chesapeake Bay. Cape Charles is a small town (the historic area is roughly a six block by six block square) that sits on the peninsula’s western coast… meaning you can sit on the beach in Cape Charles and watch the sunset right over the water. On the Chesapeake Bay, not the Atlantic Ocean, the water is calm and shallow. The picturesque town of Cape Charles is filled with Americana, all about family and beautiful surroundings, voted one of the Happiest Seaside Towns by Coastal Living. Let the beach be your playground! Check out the walkable retail district, schedule a tee time at one of Bay Creek's award-winning golf courses, or take a water adventure for fishing and cruising. brbrbrbrTraveling to/around Cape Charles, Virginia: brbr• Taxi Cabs [i.e., Cape Charles Cab Cart and Carriage, Champion Cab, Rudy's Taxicab Services]brbr• STAR Transit, local fixed route and bus servicebrbr• Uber, Lyft brbr• Bike/Cycling [Rentals: Poseidon Watersports, Trek Bicycle Virginia Beach, Rent Beach Buggies]brbrbrbrAirports:brbr• Norfolk International Airport (about 45 min by vehicle)brbr• Newport News Williamsburg International Airport (PHF)brbr• Accomack County Airport (MFV)brbr• Norfolk Ns (Chambers Fld) Airport (NGU)brbr• Langley Air Force Base (LFI)brbrbrbrPopular Landmarks:brbr• Cape Charles Museum and Welcome Centerbrbr• Kiptopeke State Parkbrbr• Cape Charles Natural Area Preservebrbr• Cape Charles Lighthousebrbr• Cape Charles Town Beachbrbr• Cape Charles Brewing CompanybrbrbrbrOther Things to Note:brbrPlease pay close attention to following the house rules. Non compliance could result in sizable fines.brbr- All guests staying at an Chesapeake Properties Vacation Rentals by Portoro (Portoro Homes) are required to sign (esignature) a rental agreement and complete identity registration.brbr- Age restrictions apply. Reservation holder must be 25 years of age.brbr- Upon arrival, we aim to ensure your safety, proper access to the home, and guest features. Should you have any questions, please don't hesitate to reach out to Chesapeake Properties by Portoro directly. brbr- Known damages incurred during your stay must be reported to the property manager immediately. brbr- Before check in, we will send you detailed directions to ensure a seamless arrival.brbr- Check-in time is 4:00 p.m. Check-out time is 10:00 a.m.brbr- We cannot guarantee early check ins or late checkouts. When it is possible to check in early or check out late, there will be a fee for anything outside of a one hour window within our standard times. If your need for an early check in or late check out is great, your best option is to book an additional night.brbr- Some homes have cameras for external monitoring only.brbr- HOTEL TAX COLLECTION: In the State of Virginia and in Northampton County, all hotel and vacation rental hosts are required to collect hotel tax. We collect these taxes within the booking transaction. brbr- Some homes offer pools/hot tubs, or access to communal pools. There is no guard around the water features when available. Use at your own risk.brbr- This is a No Pets property. A daily rate fee of $150.00 will apply for violations and you may be asked to vacate the premises with no refund at the discretion of the Host.brbr- This is a No Smoking property. Penalty fees for violations will apply and you may be asked to vacate the premises with no refund at the discretion of the Host.brbr- For the safety of guests and the home, there are noise monitoring devices. These devices only measure the decibel level and do NOT record any audio.brbrbrbrInteraction with Guests:brbrOur goal is that your vacation exceed your expectations. Chesapeake Properties by Portoro communicates via email and phone. After a booking is confirmed, rental agreement will be emailed to the guest for e-signature. Check-in instructions are sent by email and text message 14 days (or less) prior to arrival date. We offer convenient keyless entry for self-check in. We do typically check in with guests by text 1-2 times during their stays to ensure a 5-star experience and remain available for any questions. We are available to guests 24/7 for any inquiries.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

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Exceptional(5)

$532.74

/ Nightly
Private Vacation Home

Amenities in this walk to Beach, New 3bed/3.5bath

Cape Charles, Virginia, United States

Summary:brbrGetaway to this newer home that has everything you need for the perfect coastal retreat. You will love the modern beach theme decor. Open floor plan, Kitchen essentials to prepare meals. 3 ensuite bedrooms offering privacy, no bathroom wait ensuring relaxation and tranquility with unlimited hot water to wash the sand away. BBQ and Firepit. Enjoy cornhole, tetherball, Giant Connect 4. Chesapeake Bay, Main street shops and restaurants are all a short stroll or golf cart ride away.brbrbrbrThe Space:brbrStep into the welcoming foyer of A Wave From It All via convenient keyless entry. This 3 bedroom vacation home with all ensuite bathrooms offers the perfect blend of luxury, privacy and convenience. Perfect for families, couples traveling together or groups of friends for the Ultimate comfortable getaway.brbrbrbrThe front porch features comfortable rocking chairs and bench seating. This is the perfect blend of Southern Hospitality and beachside relaxation. Weather your reading a book, sipping a cool drink or simply watching the world go by this is the ultimate spot to unwind. Slow down and soak in the vacation vibes by starting your morning with a cup of coffee and a gentle sea breeze, rocking peacefully as the sun rises. In the evening gather with family and friends to watch the incredible sunset and enjoy a quiet moment under the stars. brbrbrbrAn open Concept Living Area with cozy seating, a large smart TV, gas fireplace-seasonal use. Grab your morning coffee from the well-equipped coffee bar with pod and carafe coffee pot, tea kettle, and start up coffee/tea/sugar supplies.brbrThe large center island is a great gathering place while cooking meals together in the fully equipped kitchen with high end appliances and all the necessary small appliances. The large dining room table crafted from beautiful wood is the heart of a vacation home. It encourages togetherness and conversation. Thus creating the perfect space for gathering, sharing meals, playing games, telling stories about your days adventures and making memories. brbrThe first floor coastal inspired bedroom with queen sized bed is designed to be a relaxing retreat, bringing in the serenity of the sea with light, airy colors and natural textures and pops of ocean blues, sandy beiges and crisp whites evoking the peacefulness of the coast. The bedside table with lamp and clock/wireless magnetic charger. Wind down to sleep watching the smart TV. You’ll have storage in a dresser and closet, along with an ensuite bathroom with tub/shower combo.brbrDiscover the Primary Suite on the second floor, with its Coastal Modern feel with a California king bed. Snuggle into the sumptuous linens and fluffy pillows for ultimate relaxation. The En Suite bathroom with a spa like feel, featuring a tiled walk in shower and double vanity. Make Up Mirror, hairdryer and make up wash cloths provided. Night stand and clock with magnetic charging for your devices. Lull yourself to sleep watching the smart TV. A walk in closet with dresser and ample space for storing your vacation attire to include a full-length mirror. Take advantage of the handy ottoman as you get dressed as well as utilizing for an additional single bed for that little one who couldn't sleep alone one night. brbrThe 2nd floor bunk room with 2 bunks and a trundle bed lined with comfy linens. Or you can utilize the Queen size Murphy bed built into a stylish cabinet for ease of use. The walk in closet with dresser has plenty of room to store all your vacation needs. Small desk and USB ports make it easy to charge all your devices. Catch up on binge watching on TV with remote utilizing your own streaming services. brbrEven on vacation, sometimes you need a quiet space to focus. This vacation home includes a small office, offering a comfortable and convenient workspace for those who need to check in with work or simply want a peaceful spot to write read or plan the next adventure. Fast Wi-Fi. Natural light.brbrNo need to worry about Laundry during your stay. This vacation home includes the complementary use of a full size washer and dryer with laundry soap sheets and dryer sheets. This makes it easy to refresh your beach towels, clothes and travel gear ensuring a hassle free vacation experience especially when traveling with little ones. brbrbrCeiling Fans in every bedroom to ensure comfort in any season. br2 Zone HVAC for heat and cool. Comfort on each level all year long,. brbrThe outdoor amenities at this vacation home are designed for fun, relaxation and unforgettable memories with family and friends. The gas BBQ has plenty of space for hot-dogs to steak. Challenge your group to a friendly game of cornhole, perfect for laid back competition in the ocean breeze. Try your hand at Tether ball-a fun game that keeps everyone engaged. Enjoy classic outdoor fun with a life size Connect Four, great for all ages. Just minutes from the beach, so you can easily transition from sand and surf to outdoor fun without missing a beat at this home designed for both relaxation and excitement.brComfortable seating in the Adirondack chairs around the fire pit makes it the perfect spot for late night conversations under the stars. brbrEnjoy prime location and easy access to the beach. This vacation home is just a short walk or quick golf cart ride away making it effortless to enjoy sunny beach days, waterfront dining, local shops and entertainment. This golf cart friendly community is a joy to zip around with ease. brbrbrbrbrbrAMENITY HIGHLIGHTS:brbr– Ensuite bathrooms for every bedroom and an additional 1st floor 1/2 bath. brbr– Fully equipped kitchen with many extrasbrbr– Coffee barbrbr– Gas fireplace seasonal winter only. brbr– Wireless speaker for streaming musicbrbr– Washer and dryerbrbr– Dedicated workspacebrbr– Spectrum Fiber Optic Internetbrbr– 2 Pack ’n Playbrbr– Patio with outdoor diningbrbr- Outdoor swing brbr– Sunny lounge areabrbr– Outdoor games: cornhole, tetherball, and Giant Connect 4brbr– Gas BBQ grillbrbr– FirepitbrbrbrbrThis property features a separate ADU over the garage in the back of the property. This may or may not be occupied by a guest during your stay. You have exclusive use of the entire yard.brbrbrbrGuest Access:brbrYou have access to everything at A Wave From It, except the garage. Exclusive use of the yard and all the amenities it has to offer.brbrbrbrNo fumbling with keys; self-check-in is available with digital keypad.brbrbrbrDriveway and Street parking is available directly in front of the home. Guests are not permitted to park on the grass, or to park in a way that blocks the sidewalk-ticketing by the town will apply. brbrIf you Rent a Golf Cart. Please make sure you park it in the designated Golf Cart Spot. Not on the grass or blocking the sidewalk. An extension cord to charge the golf cart is located in the storage container by the back stairs. The plug is on the front porch. Please return the extension cord to the storage container for the next guests use.brbrbrThe Neighborhood:brbrYou’ll be close to the calm Chesapeake Bay, with its white, sandy beaches – perfect for young swimmers and young at heart. Enjoy the slow, calm pace of Cape Charles’s Main Street for sipping coffee and lounging while you read a book and touring the town in a rented golf cart with the wind in your hair. You’ll also find nearby opportunities for deep-sea fishing, whale-watching, sailing, kayaking, paddle-boarding, and kite-boarding. You’ll be less than an hour from Virginia Beach and Norfolk Maritime Institute, as well as 66 miles from Chincoteague Island with its famous ponies.brbrbrDistances to nearby attractions:brbr– Central Park with Public Tennis Courts and Playground: 0.2 miles (1 min) brbr– Tennis Courts: 0.4 miles (3 mins)brbr– Eastern Shore Custom (Golf) Carts: 0.5 Miles (2 mins)brbr– CC Ryder (Golf-Cart) Rentals: 0.5 miles (3 mins)brbr– SouthEast Expeditions: 0.5 miles (3 mins)brbr– Statue of Neptune: 0.5 miles (2 mins)brbr– C-Pier: 0.7 miles (3 mins)brbr– Main Street, Cape Charles: 0.8 miles (3 mins)brbr– LOVEwork sculpture: 0.9 miles (4 mins)brbr– Cape Charles Distillery: 0.9 miles (3 mins)brbr– Cape Charles Beach 0.9 miles (4 mins)brbr– Cape Charles Brewing Company: 1 mile (3 mins)brbr– Kelly's Gingernut Pub: 1 mile (4 mins)brbr– Bay Creek Golf Course: 1.3 miles (4 mins)brbr– Poseidon Watersports: 1.4 miles (6 mins)brbr– Cape Charles Natural Area Preserve: 1.6 miles (2 mins)brbr– Kiptopeke State Park:10 miles (15 mins)brbr– Eastern Shore of Virginia National Wildlife Refuge Visitor Center: 12 miles (16 mins)brbr– Pfeiffer Riding Stables: 18.9 miles (23 mins)brbr– Chesapeake Bay Bridge-Tunnel: 21.5 miles (25 mins)brbr– SailTime Virginia: 36.2 miles (45 mins)brbr– Norfolk Maritime Institute: 38.1 miles (50 mins)brbr– Happy Winds Kiteboarding & Watersports: 44 miles (35.5 mins)brbr– Virginia Beach: 44 miles (58 mins)brbr– Chincoteague Island: 66.2 miles (1hr, 22 mins)brbrbrGetting Around:brbrThis is a golf Cart Friendly community. Local rental shops a few streets away. Otherwise walk safely on the sidewalk streets, ride a bike or drivebrbrInteraction with Guests:brI am so excited to have you enjoying all that A Wave From It All has to offer. Although, I am not on site, Guests can fee free to call and text with any questions. If at all possible limit non emergency questions from 7am-7pm. My goal is to ensure that my guests enjoy their stay and the beautiful surrounding areas.
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$571.12

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Private Vacation Home

Fully Reno'd in 2025! 1.5 block to Shops/Park & 6 to Beach. 1st floor King BR

Cape Charles, Virginia, United States

This charming 4-bedroom 3 bath house is centrally located in the historic district of Cape Charles and features a first-floor bedroom with a king bed and full bath! Originally built in the 1920's, this home has been completely gutted down to the studs and has been carefully rebuilt (completed in 2025).brbrDo you love the charm and walkability of a historic neighborhood but not the headaches of an aging home Look no further!brThis beautifully renovated home offers all the conveniences of modern living—brand-new plumbing and electric, double-pane windows, and two-zone HVAC to keep you comfortable during warm Cape Charles summers and festive winter holidays.br________________________________________brThe Homebr• 4 bedrooms, 3 king beds + 1 bunk bed (Twin XL over Queen)br• Blackout shades and white noise machines in every bedroombr• Fully appointed kitchen with quartz countertops & stainless-steel appliancesbr• Open-concept living/dining/kitchen area with direct access to a private backyardbr• Backyard porch, picnic table, and a large fire pit—perfect for al fresco dining and roasting s’moresbr________________________________________brLocation, Location, Locationbr• 2-minute golf cart or bike ride to the beach (10-minute walk)br• 1 block to Mason Ave’s restaurants, bakeries, and shopsbr• 1.5 block to Cape Charles Central Park (playground, pickleball/tennis courts, summer concerts)br________________________________________brWhat’s Providedbr• Beds made with fresh sheetsbr• 1 towel set per guest (towel, hand towel, washcloth)br• Hand soap at every sinkbr• 2 rolls of toilet paper per bathroombr• Kitchen includes: 1 roll of paper towels + 1 spongebr• 8 beach chairs & 2 umbrellas in backyard container near HVAC (let us know if anything needs replacing!)br________________________________________brNeed a Golf Cart brReach out to Smitty at CC Ryder Rentals to reserve your golf cart ahead of time! *I'll send you a few options in the welcome message after bookingbr________________________________________brMore to LovebrWe’re experienced hosts and maintain both Super Host and Premier Host status at our Smith Mountain Lake property. Feel free to ask for the link if you’d like to check reviews from past guests!br________________________________brImportant Notesbr• No parties, events, or pets. Violating this policy will result in eviction and forfeiture of your deposit.br• 2 exterior-facing Ring cameras for your security. No interior cameras.br• This is a twin-home/duplex, but entry doors are on opposite sides, and the backyards are separated by a privacy fence (see photos).br________________________________________brbrBooking DetailsbrHigh Season (June–August):br• NEW 3-night minimumbrCheck-in: 4 PMbrCheck-out: 10 AMbrbrOff-Season (September–May):br2-3 night minimum (check calendar to confirm)brCheck-in: 4 PMbrCheck-out: 10 AMbrbr________________________________________brWhether you're cooking in the kitchen, relaxing by the fire pit, or exploring Cape Charles on foot or golf cart, this is the perfect home base for your Eastern Shore getaway. We look forward to hosting you!
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$615.95

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Condo

Modern Coastal Retreat in Bay Creek Featuring Access to Club Amenities!

Cape Charles, Virginia, United States

Property Highlights:br- Spacious & Stylish: This beautifully decorated home features an open-concept layout with a cozy living area, a fully equipped kitchen, and a dining space perfect for gathering.br- 3 Comfortable Bedrooms: Sleeps up to 6 guests with plush beds and quality linens.br- 2 Full Bathrooms: Modern and well-appointed for your convenience.br- Private Outdoor Space: Enjoy a cup of coffee or an evening drink on the relaxing second floor balcony with peaceful golf course views.br- High-Speed WiFi & Smart TV: Stay connected or unwind with your favorite shows.brbrResort-Style Amenities:brYour reservation will include Bay Creek Club access during your stay. You will have access to book golf at the private golf club, use the Life Center which includes a 5,000 square-foot fitness studio, a 2,800 square-foot member lounge, access to two outdoor pools (seasonal), a toddler splash pad (seasonal) and lawn games, an expansive private beach with weekend seasonal beach rental service, explore the 350-acre Nature Preserve and dine at the Coach House Tavern.brbr- Two Miles of Private Beach Access – Spend your days soaking up the sun on Bay Creek’s exclusive sandy shores.br- Championship Golf Courses – Enjoy 27 holes of award-winning golf designed by Arnold Palmer & Jack Nicklaus.br- Pools & Fitness Center – Spend the day poolside with entire family or keep up with your workout routine in the fully equipped fitness center.br- Trails & Nature Preserve – Explore miles of scenic walking and biking trails.br-Tennis/Pickleball Courts – Play tennis or pickleball on the community courts. br- Dining & Shopping Nearby – Enjoy Cape Charles’ charming restaurants, boutique shops, and historic sites.brbrLocation:br- Just minutes from historic downtown Cape Charles, where you can explore the marina and boutique shops, rent a golf cart, and enjoy fresh local seafood or delicious baked goods. Enjoy being a short golf cart or car drive from the excitement in town then retreat back to the calmness of Bay Creek with all the resort amenities at your fingertips!
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