Vacation Rentals By Owner In Stevensville, MD

$885.23

240' Private Beachfront @Kent Island Love Point - Great for Families

Stevensville, Maryland, United States

Spacious, comfortable vacation home located on Love Point, the northern tip of Kent Island, in the heart of the upper Chesapeake Bay. This beachfront property is adjacent to the former grounds of the historic Love Point Hotel grand resort, where well-to-do families once took steamboats from Baltimore piers to vacation in style (now Love Point State Park). On the coveted northeastern side of Kent Island, you have views of pleasure craft, fishing vessels, and an array of wildlife (including dolphins on occasion) – no commercial ship traffic/anchorage in view from here.brbrThe Home: Large master suite w/private Jacuzzi and shower. Five bedrooms including a large dorm. One bedroom requires no stairs. Fully-equipped gourmet kitchen, a chef’s delight! Dining room, sun room, and two screened sun porches, all with beautiful views. Gorgeous living room with fireplace with heat exchange/blower.brbrThe Property: The grounds are nearly four acres: high ground around the house & courtyard, 1/2 acre tidal pond and wetlands toward the shore, and 240 feet of sandy beachfront. Offshore jetties create a protected lagoon by the beach, providing safety for kids swimming and those learning to kayak or paddle board. There is outstanding bird watching from the sun room and from the northeast sun porch, 40 yards from the half-acre tidal pond on the grounds. The property is directly across the water from Eastern Neck National Wildlife Refuge. Bird watching is peak over morning coffee or at dusk, depending on the species. Spectacular sunrises over the water. Plenty of space to play and wander. Catch fish and crabs right from the property, and prepare a feast for the group.brbrThe Location & Area: Ten minutes to the seafood restaurants, bars, marinas, and many other activities of Kent Narrows. It is right across the Bay Bridge from Annapolis and 40 miles to St. Michaels. Close to DC and Baltimore, it is only 60 miles from Springfield, VA. Coming across from the Western Shore, you will part with any shore traffic immediately, taking the first exit after the Bay Bridge. It seems like the other side of the world, though, once you arrive on the Island and you immediately feel your blood pressure drop.brbrAs isolated as Love Point is, itself, there is a wide range of activities close by, especially water and nature activities. Or shop at nearby outlets. See “ATTRACTIONS”, “LEISURE & ACTIVITIES”, and “SPORTS & ADVENTURE ACTIVITIES” sections for detail.brbrSpecial Notes: Six kayaks and six paddle boards provided, with paddles and life jackets. Large grass field for group sporting activities or RV/boat/trailer parking (100’ x 50’). Four wedding venues on island.brbrLinens, towels, beach towels, basic toiletries provided. See the AMENITIES sections for many more details on this gem, and hints on the local area.br brVRBO/Homeaway Story: Rented repeatedly from VRBO/Homeaway, arranging extended family & friend get-togethers at the shore, in the mountains, etc. Everyone kept asking me to go back to this property each year. Fell in love with it and bought it.brbrPerfect for family vacations and friend groups for Annapolis Boat Shows, U.S. Naval Academy Graduation, Ring Dance.

5

Bed

3

Bath

23

Sleeps

$463.75

/ Nightly

Private Vacation Home

Bayou on the Bay

Stevensville, Maryland, United States

This exceptional bayfront retreat boasts breathtaking views and contemporary elegance, making it an ideal escape. Situated close to top-notch restaurants and the Naval Academy, guests can indulge in the picturesque bay vistas while unwinding in our luxurious jacuzzi. We look forward to welcoming you soon and invite you to inquire about our exclusive wedding packages.

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Bath

Sleeps

$653.81

/ Nightly

Private Vacation Home

Spend the Holidays on the Bay at One-Level House with Private Beach Access & Panoramic Bridge Views

Stevensville, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrStunning views and your own sandy beach! Relax with the whole family as you watch the world sail by from the comfort of your family room. This beautiful waterfront home on Kent Island offers unobstructed views of the Chesapeake Bay, where local ospreys will keep you company. This single-level home is the perfect retreat for families. Spread out on the oversized lot and unwind with waterfront views on Kent Island. brbr brbrProperty Highlights: brbrStunning Bay Views: Enjoy breathtaking, uninterrupted views of the Chesapeake Bay from multiple rooms with access to a private backyard and beach brbrSpacious Living: The open layout features a large family room, dining room with seating for 8. brbrPrime Location: Close to dedicated bike paths, public beaches, an 18-hole golf course, and just a short drive to Annapolis, the Naval Academy, and the historic towns of Easton and St. Michaels. It’s an ideal home base for exploring the region or attending local weddings. brbr brbrSleeping Arrangements (Sleeps 6): brbrKing EnSuite Bedroom: brbrKing Bed brbrEnSuite Bath with luxury shower and multiple shower heads brbr brbrMiddle Guest Room: brbrTwin Bed brbr brbrBunk Bedroom: brbrTwin above Full Bed (Bunk) brbr brbrFull Bath with combo shower/bathub in the hall brbr brbrAdditional Features: brbrOutdoor Living: Private waterfront backyard with a beach, often shared with the friendly neighbors brbrModern Conveniences: High-speed internet and WiFi, flatscreen TV, full washer and dryer in the laundry room, and keyless entry for easy access. brbrLuxury Amenities: Freshly-laundered luxury linens, a complimentary toiletries Starter Kit, and boutique-level service. brbrAmple Parking: Driveway parking for 3-4 cars. brbr brbrProperty Distance to: brbrDowntown Annapolis: 19 miles (25 mins) brbrBlue Heron Golf Course: 1.2 miles brbrWashington, DC: 52 miles brbrBaltimore: 45 miles brbr brbrStarter Pack Included: brbrEssentials: A starter set of coffee, sweeteners, soap, shampoo, conditioner, lotion, hand sanitizer, paper towels, toilet paper, dish soap, sponge, and dishwashing liquid. brbrReady-Made Beds: All beds are made with freshly-laundered sheets and towels. brbr brbrHouse Rules: brbrAge Requirement: At least one member of the party must be 25 years of age. brbrPlease NO SHOES/No Smoking/No Pets brbrRespect the Home and Neighbors: Please be mindful that this is someone’s home and treat it with care. No parties or events of any kind. brbrCheck-in/Check-out: Check-in time is 4:00 pm, and check-out time is 11:00 am. brbrCome experience the perfect place to revel, relax, and reconnect on Kent Island!brbrExperience the Difference: Professionally Managed by iTrip Annapolis

Bed

Bath

Sleeps

$268.62

/ Nightly

House Boat

Floating 2 bed 2 bath condo stunning views of the bay

Stevensville, Maryland, United States

A truly unique experience, Enjoy the stunning view of the bay and nature staying on this 40 ft yacht moored at a fishing Marina. Sleeps 8 snuggly with 2 bedrooms and 2 bathrooms. Newly renovated with full kitchen and all the amenities. Small beach with grill, steps away from a tiki bar for cocktails and full menu including seafood. Mins drive from historical Annapolis and mfancy marinas and restaurants nearby. Great for families, a romance trip, fishing charters, bike rental, boat life, and zen

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Bath

Sleeps

$657.64

/ Nightly

Private Vacation Home

Waterfront on Kent Island

Stevensville, Maryland, United States

Chesapeake Bay Waterfront home on Kent Island! Enjoy year round big sky and water views from the comfort of the screened porch & family room. Fish & crab from the pier or take a dip in the bay. Great for bird watching. Open concept living and rear bedroom/rec room are perfect for relaxing and having fun with family & friends. Recently updated but still has some of it's rustic features. Close to popular wedding venues, local marinas & charter fishing boats, restaurants, Tiki bars, beaches, golfing, parks, and bike trails. Downtown Annapolis is about a 30 minute drive.

Bed

Bath

Sleeps

$804.33

/ Nightly

Private Vacation Home

Kent Island Luxury Waterfront

Stevensville, Maryland, United States

Get away from the city and enjoy the waterfront views from the property that is nestled down a private road. Perfect for families and groups who are looking to have fun in the sun and the water. You will feel right at home, yet free of your everyday stress. Leave your worries behind and bring your family or friends. Last update in April 2024.brbrThe spacebrProperty: Nestled on 17 acres, Our property is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. Guests can bring their tents as well and camp out on the spacious property. If you like water sports, kayaking, fishing, crabbing, outdoor games, or just a romantic weekend on the water. There is a 250 foot pier on the property with lights at the end of the pier. The fishing, especially at night is very good!brbrThe house is centrally located with an abundance of things to see and do! With less than a 10 min drive you can be at the Terrapin Nature Walk, Kent Island Resort, Historic Stevensville, Love Point Vineyard, and many other breweries, restaurants, and parks!brbrHome: Spacious living room, one bathroom, fully-equipped kitchen, outside and inside dining room, barbecue grill and a large deck looking towards the water and beautiful views on the main floor. Upstairs, the master bed is custom and twice the size of a king bed, couch, and private bathroom. There is a king bed and bunk bed in the second bedroom with a private bathroom. In the third bedroom, there is a queen bed that shares a bathroom with the fourth bedroom with a queen bed and a bunk bed. There is an air mattress available and plenty of space downstairs and upstairs for mattresses on the floor as well.brbrGuest accessbr- Pierbr- Dock (with accommodations from owner)br- Boat ramp that is perfect for fishing (underwater light at end of pier to attract rockfish at night), and crabbing.br- Nearby we have golfing, bird & wildlife watching, winery/vineyard, restaurants, shopping, horseback riding, nightlife, museums, and sightseeing.br**PLEASE NOTE: Only locked owner’s closets, locked office, and firepit are not available to guests.

4

Bed

3

Bath

14

Sleeps

$519.85

/ Nightly

Guest House

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville, Maryland, United States

Beautiful 2 story secluded private waterfront retreat with shared pool and hot tub access. Bring your boat and tie up to the dock for fishing or sunset cruises. 4ft average water depth at dock. Easy boat rides to local restaurants and historic towns await. 5 minute car ride to Kent Island's great restaurants and wedding venues. Convenient access to Rt 50 and only15 minutes to Annapolis. Great for Bridal parties. Bedrooms: King Bedroom Suite on main floor. Two Queen Bedroom loft area another Bedroom with three (3) full beds. Enjoy everything the Eastern Shore has to offer. The home has interior stair access from garage to the second and third floor living areas. br It does not have an elevator. Enjoy the all the conveniences and amenities this home has to offer. A great place to call homebase while you're away and enjoy Kent Island's best restaurants, dock bars and wedding venues. Nestled on 22 acres of private waterfront. Stroll on the pier or catch some crabs. Jump in the pool--relax in the hot tub. Bring your boat! This place has it all. brbrNeed more room There is a second home on this property listed as VRBO# 4131073 called Island Life 2 which sleeps 8 people!brbrLocation! Location! Location! We perfectly situated near Kent Island finest Restaurants, Dock Bars and Wedding Venues:brKent Narrows: 4.7 milesbrChesapeake Bay Beach Club-2.3 milesbrKent Island Resort-2.9 milesbrbrOther popular destinations cities are only minutes away:brAnnapolis- 15 milesbrBaltimore- 40 milesbrWashington DC- 45 milesbrEaston- 30 milesbrSt. Michael's -37 milesbrbrThis is a Non-Smoking House. brAlso No Pets, Parties or Large Groups (12 max).brbrThe Space:brThis Home is situated on a 22 acre private waterfront estate. Nature lovers will be in their glory with Kent Islands wildlife all around you. Bring the kids bikes--we have a 1/4 mile private drive for the to ride and explore. Bring your boat or catch some crabs off the dock!brbrThe first floor has the Kitchen, Dining Room, Living Room, Half Bathroom, Master Bedroom, Full Bathroom and a Washer/Dryer.brbrLocated on the second floor is Three Bedrooms:brBedroom 2: Loft area with (2) Queen BedsbrBedroom 3: Bedroom with (3) Full BedsbrbrUpstairs Bedrooms and Living Room have Smart TV's with streaming services. brThe House also has WIFI, A/C, Heating, Washer/Dryer, Microwave, Dishwasher, Coffee Maker (Both Keurig and Drip), most common spices for the cooks in the group and a fully outfitted Kitchen with all essentials.brbrBlankets, pillows, linens and bath towels ARE provided with the home.brbrGuest Access:brYou will have full access to the entire house and property, with the exception of the main home and its immediate area, garage, and exterior buildings.brbrOther Things to Note:br- The home has a set of stairs inside the garage which access the main floor of the guest home. There is an interior set of stairs on the interior to reach the upper floor where the additional bedrooms are located. The house has covered wrap around porches on the main level. These areas are private and for your use only. There is a grill in this area too for your use. There is a set of private stairs from the main level on the waterfront side of the home for convenient access to the pool and hot tub area.brbrBook Today!

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Sleeps

$1678.79

/ Nightly

Private Vacation Home

Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View

Stevensville, Maryland, United States

This short-term rental has an occupancy of 14 individuals with a max. of 6 guests being 18 years or older.brbrExperience the ultimate getaway at this gorgeous Kent Island waterfront!brbrThis 4,600 square-foot, 6-bedroom, 4.5-bathroom Long Creek waterfront retreat on over 2.6 acres of private land is perfect for your family vacation. The main level features a beautifully renovated kitchen, a dining room seating up to 12, and a breakfast area with stunning water views and sunrise vistas.brbrThis property features two entertainment indoor areas for all ages. The lower level of the main house serves as a lively entertainment hub, complete with a full bar and a billiards table, perfect for evening relaxation or friendly competition. When you step out to the backyard, you’ll find the huge detached game lounge, housing a variety of games including table tennis, air hockey, foosball, cornhole, darts, and arcade basketball hoops. An 86-inch screen TV with lounge seating provides the perfect spot for watching your favorite sports.brbrFor those looking to stay active, the property features a pickleball court along with an outdoor basketball hoop, and a peaceful sunroom for stretching and yoga in the morning. Enjoy a bike ride to a nearby trail and uncover the serene beauty of Kent Island.brbrLighthouse Haven offers a spacious upper deck and patio, an in-ground pool, an outdoor kitchen under the pavilion, and a private pier for kayaking, paddle boarding, crabbing, and fishing. Enjoy bird watching, then gather around the fire pit for storytelling and s'mores under the stars.brbrThis secluded vacation rental is only a 10-minute car ride from charming waterfront restaurants, bars, farmers' markets, shopping, and grocery stores near the Chesapeake Bay bridge. Book your stay today and create unforgettable memories!brbrPROPERTY FEATURES:brbrWaterfront: Long Creek brDock: 140ft x 6ft private dock with MLW 4 ft. Electric and water, including a sink available for guest use. 2 crab traps are provided. Guests are not permitted to tie a boat to the dock. brWater Toys: 1 two-person kayak, 1 tandem kayak, and 1 stand up paddleboard are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. brPool: 16 x 32 private pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. brFireplaces: Outdoor gas fireplace table on the deck is available for guest use. brFirepit: Outdoor firepit available for guest use. brGrill: Propane grill. Propane is provided. brLand Toys: Pickleball court (with paddles & balls), outdoor Basketball hoops, billiard, table tennis, foosball, Dart Board, cornhole, Arcade basketball hoop, available for guest use. 2 adult bikes.brWiFi: 1000 mpbs, reliably fast (good for 8-10 people or up to 12 devices)

Bed

Bath

Sleeps

$770.46

/ Nightly

Private Vacation Home

Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.

Stevensville, Maryland, United States

Recently updated 4 bedroom home in a centralized, quiet, location with no shortage of amazing views of the Chesapeake Bay! This home will fulfill the needs of every family member, regardless of age, for your ideal getaway. With a convenient location just miles from the Bay Bridge, Kent Narrows, and Annapolis, the local attractions are just the beginning for this prime location. You will have access to our entire home! The 4 bedrooms and 3 baths (2 of which are ensuite) are all located on the main floor. Just 2 steps down from the fully stocked kitchen and coffee bar you enter the open living and dining area with plenty of room for all! Ready to unwind after a long day Step outside into the screened in patio featuring a gas firepit and couches. Looking for happy hour with a view Just outside there is a set of stairs that lead you up to the roof top deck with Adirondack chairs. The backyard offers endless activities with plenty of space for the kids to run, a friendly corn hole competition, or smores over the wood burning fire pit. Back inside you'll find everything you need for a relaxing, carefree stay with hotel quality sheets, plush towels, and hair dryers to just begin the long list of amenities. Enter into the basement and you'll find the 4th full bath along with a wet bar, pool table, dart board, and kids area! The home is centrally located with an abundance of things to see and do! Love Point Vineyard is just 1.5 miles away, and with less than a 10 min drive you can be at the Terrapin Nature Walk, Kent Island Resort, Historic Stevensville, Chesapeake Bay Beach Club, and many other breweries, restaurants, and parks!

Bed

Bath

Sleeps

$499.58

/ Nightly

Private Vacation Home

Love Point Waterfront Home....Chesapeake Bay views....Pets OK

Stevensville, Maryland, United States

Maryland’s Chesapeake Bay is an ever changing panorama of spectacular sunsets, teeming wildlife, graceful sailboats, and impressive ships. We invite you to enjoy it from a truly wonderful, tranquil, historic location, Love Point! Located just 4.5 miles north of the Bay Bridge, we are 10 minutes to shopping, 20 minutes to historic Annapolis, 40 minutes to Baltimore and 50 minutes to Washington, DC. This charming 2800 sq.ft. landscaped ranch home is situated on 1+ acres with 200' of shoreline. There is a dock with ladder providing easy access to the bay for boating, fishing and swimming (sandy bottom). Afterwards enjoy the hot/cold OUTDOOR SHOWER!! The interior spaces are comfortably furnished - a cathedral ceiling spans the kitchen/family room space with large windows. A separate living room looks out to the street and additional multipurpose room with bathroom and sliding doors to back deck offers several public sitting areas. Tables, chairs and loungers outside on the trex deck allow one to relax with a sea breeze while taking in the glorious view. A fire pit, shade trees, hammock, dock, and deck compliment the private and expansive back and side yard. brbrFurnishings are an eclectic and colorful mix of antiques and hand painted furniture which has been collected on the eastern shore and abroad. TVs with cable or fire sticks are in 3 rooms. A piano for music lovers is in the living room. There are hardwood floors throughout and many ceiling fans as well as adjustable ac units. The finished basement serves as a space for foos ball, board games, puzzles, etc. A side adjacent lot allows extra space for soccer, volleyball etc.brbrThe house sleeps 4-6 people most comfortably. On the mail level there are 6 beds and an additional queen downstairs. br…..4 twin beds, br.... 2 queen size beds br.... 1 king bedbrbrLinens and towels are provided for 6. Groups larger than 6, have the option of paying extra or bringing their own linens.brThe kitchen is fully equipped for all your cooking needs providing a dishwasher, microwave, 2 coffee makers, serving dishes, etc.brbrbrCome and enjoy! You will be delighted and refreshed.

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Sleeps

$594.85

/ Nightly

Private Vacation Home

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville, Maryland, United States

Over 3000sf. Fully stocked, (just remodeled) kitchen, study, formal dining room, large living room, full bath, all downstairs. Upstairs, 4 bedrooms (2 Queens, 2 sets of twins) and 3 full baths. 2 Galley stairs (very steep) and main staircase. Large pool and expansive open space with piers and water access. Canoe and kayaks available.

Bed

Bath

Sleeps

$452.89

/ Nightly

Private Vacation Home

Welcome to The Blue Crab House Stevensville Maryland Eastern Shore

Stevensville, Maryland, United States

Welcome To The Blue Crab House br Full of your finest eastern shore charm in Stevensville Maryland this spacious 3 bedroom 2.5 bath includes an open space floor plan with an abundance natural light, large outdoor space includes a large deck overlooking beautiful landscaping. Perfect for entertaining. Plenty of off street parking, well equipped for an enjoyable stay. Several wedding venues within one and a half miles. Naval Academy is a twenty minute drive and so is Annapolis Md.

3

Bed

2

Bath

6

Sleeps

$1514.74

/ Nightly

Private Vacation Home

Kent Island Waterfront Retreat

Stevensville, Maryland, United States

brWelcome to your waterfront paradise! This stunning home offers the epitome of luxury and relaxation with its prime location and abundant amenities. With 5 bedrooms and 5 1/2 bathrooms, there's plenty of space for friends and family to unwind and recharge.brbrThe spacebrFrom the moment you step inside, you'll be greeted by breathtaking views of the Bay Bridge visible from every room, creating a seamless blend of indoor-outdoor living. The spacious living room provides the perfect setting for gatherings and entertainment, while the fully equipped kitchen and full bar make dining and hosting a breeze.brbrFor the competitive spirit, indulge in friendly matches on the Foosball and ping-pong tables or relive arcade classics for endless entertainment. And when it's time to cool off, step outside to your private outdoor pool, where you can soak up the sun and take refreshing dips against the backdrop of stunning waterfront vistas.brbrBut the allure of this retreat doesn't end there. Outdoor enthusiasts will appreciate the long fishing pier, offering unparalleled opportunities to cast a line and reel in the day's catch while surrounded by the serene beauty of the bay.brbrWhether you're seeking relaxation or adventure, this waterfront haven promises an unforgettable escape for your next vacation or special occasion. Book your stay today and immerse yourself in the ultimate blend of luxury and leisure on the waterfront.brOther things to notebrbrFor your security and others, there are exterior security cameras at side door and patio door

5

Bed

5

Bath

16

Sleeps

$337

/ Nightly

House Boat

Chesapeake Houseboat Getaway on Kent Island, Maryland

Stevensville, Maryland, United States

Looking for a peaceful waterfront, floating experience on the Chesapeake Bay Julia’s Arc has got you covered. Easy access to the boat at high or low tides from a 5 foot wide floating dock. Well protected in the marina and yet right next to beach, waterfowl and the nautical life. Come to relax, come to celebrate, bring your kids or getaway for a romantic celebration. Only 20 minutes to Annapolis, 50 minutes to Chestertown, 45 minutes to Easton, St. Micheals and Oxford. With a full galley that any chef would be pleased with, you can cook up a feast or throw an intimate party. Some even come for work. The wifi signal is fast enough to stream your favorite shows and games or a work video call. Come restore your peace, restore your balance you won’t be sorry.

Bed

Bath

Sleeps

$791.38

/ Nightly

Private Vacation Home

Kent Island Waterfront | Pool | Stunning View

Stevensville, Maryland, United States

New Hot Tub available for guest use by July 1, 2026.brbrRelax and unwind. Located on the Chesapeake Bay, this charming vacation rental features 3 bedrooms, 2 bathrooms, and a renovated kitchen that boasts exquisite high-end granite countertops, a gas range, and stainless steel appliances.. brbrAn extra full bath, strategically placed, offers easy access from the pool and outdoor areas. The open floor plan in the living areas, providing a cozy spot to enjoy the mesmerizing views of Kent Island's waterways and seasonal bird migrations. Watch the sunrise over the bay. Dine indoors or al fresco, the choice is yours.brbrReap the benefits of neighborhood living in this sought-after part of Queen Anne's County. Just a 3 - 5 minute drive to the Cross Island Trail, Blue Heron Golf Course and Driving Range, and the Mowbray Park tennis and pickleball courts and 10 - 15 minutes from some of the best restaurants, shopping, cafes, bars, wineries, nightlife, and mom-and-pop shops. All the perks of Queen Anne's County living are an easy drive away. Book your getaway today!brbrPROPERTY FEATURES:brbrWaterfront: Eastern Chesapeake BaybrDock: Private dock with 130 ft of shoreline, 4.6 ft MLW with electric at dock but no water. Guests are not permitted to tie a boat to the dock.brWater Toys: 4 Kayaks, and crabbing gear available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency.brPool: Private pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels.brHot Tub: New Hot Tub available for guest use by July 1, 2026.brLand Toys: Corn hole is available for guest use.brGrill: Charcoal grill. Charcoal is provided.brWiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.

3

Bed

2

Bath

7

Sleeps

$754.38

/ Nightly

Cottage

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Stevensville, Maryland, United States

Welcome to our coastal cottage, a haven for your perfect getaway in a community that offers 3 different locations to access and view the water. This charming home boasts a quintessential coastal cottage design that exudes charm and relaxation. Conveniently located minutes away from numerous wedding venues. Annapolis, Washington DC, Baltimore as well as many charming Eastern Shore towns are all less than an hour's drive away. Amazing screened-in porch (now with a 3 season enclosure), farm style dinner table, fireplace, large screen TV and cozy swing bed. Fenced-in back yard with cedar barrel sauna under tall mature pines!brbrUpon your arrival you'll be welcomed by the natural beauty of our quaint gardens to take you back in time to the simpler days. Designed to bring feelings of enchantment and relaxation, inviting you to escape the hustle and bustle of modern life and immerse yourself in a peaceful and natural oasis. brbrEnter into the open concept living room and kitchen with cathedral ceilings to connect with family and friends. Snuggle up on the couch to watch a movie or gather in the kitchen to prepare your favorite meal. For an authentic Kent Island Maryland experience, try Chesapeake Blue Crabs. brbrOnce you step onto the screened-in 3 season porch you'll never want to leave. Dine al fresco, read or nap on the pillow filled swing bed or simply relax and enjoy a tall glass of iced tea while you breath the fresh outdoor air and listen to the symphony of songbirds. Chill in the air Fire up the gas fireplace and watch the game on the TV above the mantle.brbrSpill out past the porch onto the patio to enjoy an appetizer and drink while you cook up dinner on the BBQ grill. To top off the evening, sit back in one of the Adirondack chairs surrounding the Breeo firepit for smore's and stories. You'll never want the evening to end.brbrBut when you can't keep your eyes open any longer, retreat into the cozy bedrooms where you'll find premium Paragon 100% cotton sheets on spacious king beds. Each bedroom has access to its own bathroom stocked with luxurious towels and bathrobes. Close the blackout curtains and enjoy a quiet peaceful night's sleep. brbrAs you rise from slumber, wander over to the one-of-a-kind coffee & tea bar. Delve into the whimsical world of our mug wall, where you can pluck the perfect cup just for you. It's a small but joyful moment, ensuring your morning starts with a touch of happiness and a cup that's uniquely yours. brbrIndulge in the ultimate relaxation experience with our private 6-person barrel sauna. Take your relaxation to the next level with this exclusive addition, offering a luxurious escape right on the premises. When you're ready to start your day, each bedroom has a make-up vanity with a magnifying mirror that lights up and a full-length mirror to make sure you are dressed to perfection. brbrWhere will you go and what can you do brbr1.) Stay home, no need to drive:br*Hire a chef for an in-home chef made authentic Chesapeake Bay dinnerbr* Hire an artist for an in-home paint partybr* Hunker down on the screeded in porch on a stormy night to watch Mother Nature's showbr* Smore's by the firebr* Play cards or Dominosbr*Classic, watch a movie on one of our 4 smart TV'sbrbr2.) Enjoy local activities at some of the best spots in Maryland. We are locals and can help you find all the hot spots!br* Spa weekend br* Winery tourbr* Island bike trail & nature parksbr* Golf weekendbr* Charter a boatbr* Dine at amazing local restaurants with beautiful viewsbrbrWhether you are on Maryland's picturesque Eastern Shore to relax, visit family & friends, attend one of the popular Kent Island wedding venues or off on adventures, this house is perfect for you. brbrbrOther things to note: brbrAccessibility Features:br* Zero-step threshold front door, back door and patio doorbr* Exterior Keyless lockbr* All doorways and hallways are 36 widebr* One level home with continuous hard surface flooring throughout the homebr* Adequate parking space for vehicles with rampsbr* Interior lever door handles throughout the homebr* Adequate space for movement around furniturebr* Below counter microwavebr* Bathroom grab bars in shower and above toiletbr* Step in shower 5br* Handheld shower head combobr* Shower seat height 18br* Available upon request: Agrish brand portable toilet safety railsbr* Toilet seat height 18br* Bathroom Pedestal sinksbr* Bed Height 24br* Service dogs are welcomebrbrCamera:brGuest acknowledges the presence of one (1) exterior Ring doorbell with built in camera. By booking, you are consenting to video and sound being recorded, the camera is on and recording 24/7. The Ring Doorbell camera is located outside at the front door and views the walkway up to the front door.

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Bath

Sleeps

$318.0

/ Nightly

Country House

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Stevensville, Maryland, United States

Get ready to relax in this brilliant 3-bedroom coastal-country home in Stevensville. Remodeled and refurnished completely in 2024 with 2 king beds and 2 queen beds, this adorable property offers a cozy retreat for our guests. Enjoy the convenience of amenities like heating, AC WiFi, and washer and dryer machine. The 2 bathrooms feature showers and hair dryers for added comfort. A great place to call homebase while you're away and enjoy Kent Island's best restaurants, dock bars and wedding venues. Nestled on 22 acres of private waterfront. Stroll on the pier or catch some crabs. Bring your boat! We hope you enjoy your stay. brbrbrAnnapolis- 15 milesbrBaltimore- 40brWashington DC- 45brEaston- 30brSt. Michael's -37brbrLocation! Location! Location! We perfectly situated near Kent Island finest Restaurants, Dock Bars and Wedding Venues:brKent Narrows: 4.7 milesbrChesapeake Bay Beach Club-2.3 milesbrKent Island Resort-2.9 milesbrbrOther popular destinations cities are only minutes away:brAnnapolis- 15 milesbrBaltimore- 40brWashington DC- 45brEaston- 30brSt. Michael's -37brbrThis is a Non-Smoking House. brAlso No Pets, Parties or Large Groups (8 max.).brbrThe Space:brThis Home is situated on a 22 acre private waterfront estate. Nature lovers will be in their glory with Kent Islands wildlife all around you. Bring the kids bikes--we have a 1/4 mile private drive for the to ride and explore.brbrThe first floor has the Foyer, Kitchen, Dining Room, Living Room, Den, Full Bathroom, and a Washer/Dryer.brbrLocated on the second floor is Three Bedrooms:brBedroom 1: (1) King Size Bed brBedroom 2: (1) King Size BedbrBedroom 3: (2) Queen Size BedsbrbrAll Bedrooms, Living Rooms and Dens have Smart TV's with streaming services. While all the bedrooms have doors for privacy, you have to walk through the Bedroom 3 to access Bedrooom 2. brThe House also has WIFI, A/C, Heating, Washer/Dryer, Microwave, Dishwasher, Coffee Maker (Both Keurig and Drip), most common spices for the cooks in the group and a fully outfitted Kitchen with all essentials.brbrBlankets, pillows, linens and bath towels ARE provided with the home.brbrGuest Access:brYou will have full access to the entire house and property, with the exception of the main home and its immediate area, garage, and exterior buildings.brbrOther Things to Note:br- The home is two stories with necessity to climb a few stairs to access the entry and stairs to access the upper floor inside.brbrBook Today!br

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$284.71

/ Nightly

Condo

Kent Island Waterfront Cottage

Stevensville, Maryland, United States

Private 2 bedroom 1 bathroom waterfront cottage on the Chester River. Enjoy the solitude that this property offers, including spectacular sunrises and fishing off the pier (rockfish are very abundant). Perfect for families, couples, or friend groups who are looking to get away from it all.brbrIf you are traveling with small children, we have high chairs and a pack and play available upon request.brbrRecent June 2022 updates include new memory foam mattresses, new outdoor lounge chairs, and Roku.brbrThe spacebrThere are two bedrooms, one bathroom, a spacious living room (includes a pullout couch), kitchen, and a large deck looking towards the water.brbrThere is plenty of yard space for outdoor games. If you like water sports, fishing, outdoor games, or just a romantic weekend on the water, the property has a 250 foot long pier with underwater fishing lights at the end. Love Point is where you want to be!brbrGuest accessbrEntire cottage, entire cottage patio, entire yard, entire pierbrbrOther things to notebr- Pier (fishing poles and nets available upon request)br- Dock (with accommodations from owner)br- Boat ramp that is perfect for fishing (underwater light at end of pier to attract rockfish at night), and crabbing.br- Nearby we have golfing, bird & wildlife watching, winery/vineyard, restaurants, shopping, horseback riding, nightlife, museums, and sightseeing.br-Garage is not included in the rental

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$1276.5

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Private Vacation Home

Chesapeake Bay Waterfront ARTectural Home

Stevensville, Maryland, United States

SPECIAL RATES FOR JANUARY AND FEBRUARY 2026! CHECK CALENDAR.brWelcome to this most relaxing home for your getaway. Perfect for vacations, retreats, meetings, anything that you can imagine.brTravel just 4 short miles from the Bay Bridge to this 2 story home overlooking the Chesapeake Bay. Sunsets galore and constantly changing views of Ships, Sailboats, Osprey, Eagles, Heron and much more. Calm water and strong winds are all beautiful to watch from our two levels. 12' x 52' covered patio on main level and 12' x 52' enclosed sunroom on the upper level with heat and AC.br3200 square ft home full of art and artful touches. Open floor plan on both levels with plenty of space to spread out. Main level master and 2 masters upstairs each with full bathrooms and an additional full bath on main level. Gourmet kitchen with a large island that seats 6. A custom made dining table that seats 10. brLarge pool in the back yard that has an unobstructed view of the Bay. Tanning ledge, lights and umbrella holders for a relaxing swim regardless of time of day or the weather.

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$1332.29

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Private Vacation Home

The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground!

Stevensville, Maryland, United States

⭐ THE HIGHLIGHTSbr • Private waterfront setting on Kent Islandbr • Resort-style pool with water views br • Firepit with Adirondack chairs on sandbr • Walk to the Bay beach for sunsetsbr • 5 bedrooms + multiple living spacesbr • Kids playroom + gamesbr • Playground newly installedbr • Big dining tables for meals togetherbr • “Car bar” for entertaining & fun setupsbr • Record player for laid-back eveningsbr • Eastern Shore decor brbrWe are EXTRA kid-friendly: playroom, pirate bunk room, baby gear (baby tub, diaper genie, high chair, pack n play, stools for the sink all included), toys, kid-sized beach chairs, kids books, fenced pool (when open), lawn games, children’s pool cabana, and an awesome playground. brbr⸻brbr ️ MADE FOR GATHERINGbrbrThe Great Room: soaring ceilings, panoramic water views, and space for everyone to spread out.br • Oversized sectional + electric fireplacebr • Record player + 65” TVbr • Dining table with water viewsbr • Kids play areabrbrThe Living Room: the softest sofa, swivel chairs, and over a dozen board games brbrThe “Unplug Zone”: TV-free gathering space in front of a decorative fireplace and art by local artist Kim Hovell.brbrWhether you’re hosting a big family dinner or just hanging out in pajamas, the layout makes it easy.brbr⸻brbr ️ EAT, DRINK & LINGERbrbrThe Kitchen: fully stocked for preparing real meals and easy hosting — from waffle mornings to seafood feasts.br • Full-size appliances + dishwasherbr • Waffle maker, bakeware, and serving dishesbr • Two indoor dining areas (seats 18 total)brbr☕ “But First, Coffee” BarbrKeurig, Nespresso, French press, and logo mugs for the perfect cup.brbr⸻brbr SLEEP WELLbrbrAt The Landing, all beds are freshly made with white linens and duvet and two types of pillows depending on whether you like soft or firm.brbr • Primary Suite: King bed, panoramic water views, spa-like bath with soaking tub, coffee bar, TV, laundry, and office nookbr • Bedroom 2: Queen bed, water views, TV (shares full bath)br • Kids Bunk Room: Two sets of bunks (sleeps 4) with playful pirate themebr • Bedroom 4: Queen bed, en-suite bath, TV, coastal décorbr • The Landing Lounge (Bedroom 5): Daybed converts to queen sleeper; barn door + blackout drapes for privacy. Features “The Landing” logo wall.brbr⸻brbr OUTDOOR FUN brbr Private Pool (April–October)brFully fenced when open, with loungers, umbrellas, and big water views. It feels like your own little resort.brbr Firepit on the WaterbrEight Adirondack chairs, propane firepit, and solar lights — perfect for s’mores, stories, and early-morning coffee.brbr Outdoor Dining & Entertainingbr • Dining table for 10br • Bistro table for twobr • “Car Bar” for crab feasts, buffets, or lemonade standsbrbr Waterfront + Beach AccessbrLocated on Chews Creek (great views and wildlife — swimming not recommended). A 10-minute walk brings you to the community Bay beach for sunsets and sandy toes.brbrBeach chairs and lawn games are provided.brbr— brbrCLEANINGbrbrProfessional cleaning, hotel-quality linens, and full turnover included — no extra linen or supply fees.brbr⸻brbr KENT ISLAND LOCATIONbrbrYou’re minutes from:br • Wineries & waterfront seafoodbr • Marinas & boat rentalsbr • Golfbr • Parks, trails & art galleriesbr • Groceries, Target & StarbucksbrbrEasy access to Kent Narrows, Historic Stevensville, Queenstown, Wedding Venues, and day trips to St. Michaels, Naval Academy, Annapolis, Easton, and Oxford.brbr⸻brbr❤️ A NOTE FROM YOUR HOSTbrbrThe Landing was designed to be a place where people feel comfortable, welcomed, and cared for. Hosting is personal to me, and I’m always available to help make your stay easy and special — whether that’s recommendations, questions, or making sure everything feels just right.brbr⸻brbr⭐ THE LANDING IS PERFECT FOR…brbrFamily vacations, multigenerational trips, friends’ getaways, bachelorette parties, celebrations, or anyone looking for a warm, fun, waterfront escape with room to actually enjoy being together where both kids and grown-up can have fun!brbrTHINGS TO KNOWbrbrYou may access the entire home and yard with the exception of the garage and the two locked closets upstairs. brbrOur neighbor, Kim, is lovely and will be available to assist you during your stay. brbrPrimary guest must be 25+ and be present for the duration of the stay. brbrThe Landing is located in a quiet residential neighborhood. The onsite caretaker is the next-door neighbor. brbrPlease note that part of Island life is having well water. As a result, bottled water is recommended for drinking / cooking. brbrNo smoking anywhere on property (inside or outside). No parties or events.brbrSwim in pool, beach, and waterfront at your own risk, no lifeguard, owner and manager assume no liability.

5

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4

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12

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