Vacation Rentals By Owner In Stevensville, MD

$639.79

Private pier at multi-suite waterfront home on the Bay with Hot Tub (Open!)

Stevensville, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWelcome to this beautiful waterfront home with a private pier that sits only 50 feet back from the Chesapeake Bay. Located on Kent Island, this home boasts breathtaking views from multiple spots both in and outside the home. Enjoy your morning coffee from the fully-furnished sunroom, and watch the boats go by on the Bay from the private waterfront deck. After grilling a homemade dinner, chill out in the hot tub (open Fall-Late Spring) on one of the other 2 back decks on the house. The home has a total of 4 Bedrooms and 4 Baths, 2 of which are En Suite. brbr brbrThis home is wonderful for families, golfers, boaters, fishermen, bicyclists and runners/walkers. For golfers, the beautiful and challenging executive golf course, The Blue Heron Golf Course, is one mile from the house. brbr brbrBicyclists, walkers and runners can enjoy miles of trails on Kent Island. Two of the most popular are the Kent Island South Trail and the Cross Island Trail. brbr brbrSLEEPING ARRANGEMENTS 4 Bedrooms/4 Baths; sleeps 8: brbrBayside En Suite Primary Bedroom: brbr-Queen Bed brbr-En Suite fully-renovated Bath with luxury shower brbr-Views of the Bay and entrance to one of 3 decks brbr brbrSeashell En Suite Bedroom: brbr-Queen Bed brbr-En Suite Full Bath with stand-up shower brbr brbrCoral Bedroom brbr-Queen Bed brbr-Full Bath shared with Surf Bedroom brbr brbrSurf Bedroom brbr-Queen Bed brbr-Full Bath shared with Coral Bedroom brbr brbr4th Full Bath with double vanities and shower located off the Den. brbr brbrHIGHLIGHTS: brbr-Private Waterfront pier and furnished deck brbr-Hot tub brbr-2 more private decks in the backyard brbr-Fully-furnished sunroom, Family room and Den brbr-Gas Grill brbr-Dining Room table seats 6 brbr-Breakfast Bar seats 3 brbr-Deck Dining Table seats 4 brbr-High Speed Internet and WiFi brbr-Flatscreen TVs in both the Family room and Den with Roko brbr-Luxury linens, complimentary toiletries Starter Kit, and boutique-level service brbr-Parking for 3-4 cars on the driveway brbr-Full Washer & dryer in Laundry Room brbr-Keyless entry. Drive straight to your rental home, enter the lock code on the front door to enter the home. brbr brbrProperty Distance to: brbr-Downtown Annapolis – 19 miles (25 mins) brbr-U.S. Naval Academy – 19 miles (25 mins) brbr-Washington, DC – 48 miles brbr-Baltimore - 43 miles brbr brbr*Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid. brbr* All beds are ready-made for you with freshly-laundered sheets & towels. brbr brbrHouse Rules brbrReservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Be respectful of the house and contents - it is someone's home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood. No parties or events of any kind. brbrCheck-in time: 4:00 pm brbrCheck-out time: 11:00 am

4

Bed

4

Bath

8

Sleeps

$439.9

/ 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.

2

Bed

2

Bath

6

Sleeps

$742.0

/ Nightly

Apartment

n4 bedroom bayfront oasis with spectacular views!

Stevensville, Maryland, United States

Chesapeake Bayfront Oasis offers a spacious, serene escape with panoramic bay views from every room, a private outdoor deck, and open-concept living for easy relaxation; enjoy on-site kayaks and a luxurious jacuzzi, plus a fully equipped kitchen, cozy bedrooms, fresh linens and toiletries, high-speed Wi-Fi, and indoor-outdoor living—just 25 minutes to the Naval Academy and 5–10 minutes to top local dining, with sunrise and sunset momentsi by the water.

4

Bed

3

Bath

5

Sleeps

$746.48

/ Nightly

Private Vacation Home

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.

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Bath

Sleeps

$768.0

/ Nightly

Cottage

Chessie Cottage-Chesapeake BaynGreat views from easy single floor living!

Stevensville, Maryland, United States

Welcome to Chessie Cottage on The Bay! There is an intangible quality to a cottage coming from a unique combination of architectural details, use of historic materials, enchanting setting. These are but a few of the elements creating this charming storybook cottage. Exit Bay Bridge, a short 4-mile drive delivers you to our little neighborhood, and at the final bend in the road, we have private parking. Accessing the house immediately via the brick/limestone walkway leads to a true cottage entrance; a steeply gabled roof over mahogany arched Dutch door, a true storybook welcome home! Bay views greet you before ever entering the cottage, visible from the Dutch door straight through the west facing wall of windows overlooking the bay. Three windows, each 5ft. tall x 8ft. long plus double glass French doors provide over 30ft of uninterrupted open shoreline views. The morning sunrise filtering through the trees lights the east Dutch door window starting a day of relaxation in this cozy cottage, ending with the sunsets and long-lasting afterglows on the water. The Chesapeake Bay is the largest estuary in the U.S., 3rd largest in the world, and one of the most productive bodies of water in the world. brWe offer you endless views from our 150+ feet of private shoreline. brThis custom home was created and built by artists so when NOT watching the never-ending array of eagles, herons, ducks, nesting ospreys, songbirds, dragonflies, and everything that floats, go by; from jet skis, crab boats, sailboats, to giant freighters and cruise ships traveling the deep-water channel…there’s endless interest & beauty all around. Open floorplan provides amazing views from every room, every seat. Large, well appointed, open, airy kitchen is ready to make all your meals memorable. Dine stylishly at the mid-century-modern Danish table or sit high and comfy at the custom designed butcherblock peninsula, originally from the Old Faithful Inn kitchen, Yellowstone National Park. Kitchen sink is, itself, a treat; a Ruvati 45” long, stainless steel Wonder Station of prep, serve, buffet, clean-up cheffing fun. Soft natural light pours in from 3 enchanting rooftop eyebrow windows, sunset reflects thousands of brilliant sparkles against the hand-laid ironstone wall in the living area. Main living area has 2 Queen sleeper sofas, one in a cozy alcove easily doubles as a dedicated office space with tilt-top coffee table for laptop, and office supplies. (If you must work, you can leave things set up to take a ‘bay break’.) Two private bedrooms each with king beds, smart TV’s, private en suite bathrooms, and inviting bay window seats for private moments reading or just watching the water. There is a 3rd full bath which services the main house located just past the well-stocked library nook where you’ll find games, puzzles, cards, and books for kids to adults. brbrWe hope you find our home to be as enchanting, relaxing, and restorative as we do. Someday it will become our everyday home, but until then we look forward to sharing it with you. br

2

Bed

3

Bath

8

Sleeps

$1588.23

/ 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

$328.6

/ Nightly

House Boat

40' Bristol sailboat with spectacular views

Stevensville, Maryland, United States

Nestled in Stevensville, this adorable boat features a cozy bedroom with a queen bed and a bathroom with a shower. Perfect for a romantic getaway or a solo retreat, this charming property offers a unique experience on the water. Imagine waking up to the gentle rocking of the boat and enjoying your morning coffee on the deck. Gorgeous sunrises and sets.. You're sure to make fantastic memories with a stay at our place. This is a non smoking property.

1

Bed

1

Bath

2

Sleeps

$865.8

/ Nightly

Private Vacation Home

Pool & Stunning Water Views: Kent Island Home!

Stevensville, Maryland, United States

Private Pool w/ Waterfall | Scenic Sunroom | 1,750 Sq Ft brbrYour slice of paradise awaits at this waterfront vacation rental in Stevensville, MD! Spend your days soaking up the sun by the pool while enjoying panoramic views of the bay. After hitting the beach at Sandy Point State Park, return to the 3-bedroom, 2-bath home and watch the sunset as you sip a refreshing drink by the fire. This property also boasts multiple outdoor dining tables, perfect for enjoying a meal as the sun sets!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bed br- Bedroom 2: 1 queen bed, 1 lofted twin bedbr- Bedroom 3: 1 queen bedbr- Living Room: 1 queen sleeper sofabr- Sunroom: 1 queen sleeper sofabrbrOUTDOOR LIVING br- Private pool (unheated)br- Dining area w/ umbrellabr- Gas fire pit, lounge seatingbr- Outdoor showerbr- Dockbr- Community park & boat ramp (kayaks & paddle boards) brbrINDOOR LIVING br- 5 Smart TVs, Sonos speakerbr- 2 dining tablesbr- Picture windowsbr- Ceiling fansbrbrKITCHEN br- Stove/oven, refrigerator, dishwasherbr- Microwave, wine coolerbr- Keurig coffee maker (bring your own coffee)br- Cooking basics, dishware/flatwarebr- Trash bags/paper towelsbrbrGENERAL br- Free WiFi br- Central & mini-split air conditioning/heatbr- Linens, towels, shampoo, conditioner, hair dryerbr- Washer/dryer, iron/board, hangersbrbrFAQbr- 4 exterior security cameras (facing out)brbrACCESSIBILITYbr- Single-story home, 3 steps to enterbrbrPARKINGbr- Driveway (6 vehicles)brbr-- THE LOCATION --brbr- 2 miles to various restaurantsbr- 3 miles to Chesapeake Bay Beach Clubbr- 9 miles to Sandy Point State Parkbr- 6 miles to Kent Narrows, MDbr- 16 miles to Annapolis Naval Academybr- 36 miles to Baltimore/Washington International 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- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story home requires 3 steps to enterbr- The on-site boats, pavilion, and outdoor kitchen area are not available for guest usebr- Your safety matters. This property features 4 exterior security cameras: 1 camera is by the front door facing the front entrance, 1 camera is on the left side of the home facing the side yard, 1 camera is by the back door facing the back entrance, and 1 camera is on the back of the home facing the backyard. The cameras are outward facing and do not look into interior spaces. The cameras are activated by motion and will record video and sound while guests are in residence

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Select Dates for Price

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.

Bed

Bath

Sleeps

$687.94

/ 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!

4

Bed

4

Bath

10

Sleeps

$286.38

/ 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.

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Bath

Sleeps

$932.4

/ Nightly

Private Vacation Home

Stay on Kent Island by Kentmorr Marina for USNA Graduation Week!

Stevensville, Maryland, United States

brbrKI Beach House II: Over 2000 sq ft 4 bedroom/2 bath home is a modern fisherman's village on the corner by the marina. Not only a great place to stay to visit the Naval Academy, attend a destination wedding or event, but perfect for a small company strategy session, retreat, or a central location to see what MD, DC, VA, DE, and PA have to offer. Walk in from the oversized deck to enjoy open entertaining including big flat screen Internet TVs. Picturesque Panoramic Chesapeake Bay Water Views await you.brbrWelcome to KI Beach House II, offering comfortable water view accommodations for 8 adults, with a maximum occupancy of 14 including children. This 2-story spacious more than 2000 sq ft nautical home features 4 bedrooms and 2 baths, situated as a modern contemporary fisherman's village on the corner by the Kentmorr Marina, across from the Kentmorr Beach Bar and Grill, and conveniently side-by-side with our original KI Beach House. Stroll through the waterfront neighborhood or walk/bike along the South Island Trail. brbrIdeal for hosting your midshipmen, visiting the Naval Academy, attending destination weddings or local events, or hosting small company strategy sessions and retreats. Our homes also serve as a central location to explore MD, DC, VA, DE, and PA. brbrImagine sipping morning coffee on the deck watching the charter boats get ready for the big stripers, as the dawn breaks over another perfect day. Step inside to enjoy spacious entertainment areas, complete with large flat screen Internet TVs. Downstairs, two bedrooms await, one with a King bed and the other with a Queen bed, along with two sofas in the living room and a daybed with trundle in the sitting area. Ascend upstairs to the sprawling nautical-themed expansive Captain's Quarters featuring a Desk, King bed, Twin bed, Sofa, and small Futon for additional sleeping space. This King plus bedroom is separated from the mate's Queen bedroom by a huge striking red anchor-themed soaking tub and tiled shower jack and jill bathroom, offering peace and relaxation amidst the maritime ambiance. Perfect for the fisherman yet classy enough for the girlfriend getaway on the Shore! brbrThe beds are all made when you arrive. Extra sheets for the daybed/trundle, sofas and such are in the laundry room china closet. Additionally, there are extras upstairs in the Master Bath bottom right drawer. There are extra sheets and towels for your use and a washer and dryer are in the home. We are fully stocked with dishes, pots, and pans, drip coffee pot, blender, etc. The home has both propane and charcoal grills (bring your charcoal). We supply at least 2 rolls of toilet paper per bath, body wash/shampoo, a roll of paper towels, a few trash bags, etc but don't supply lots of paper/plastic type items. Food Lion and Safeway are nearby for groceries as are dollar stores, liquor stores, and a Target.brbrWe are located on Kent Island in Stevensville MD just minutes from Kent Narrows. Come by Car, Boat, Bus, or Plane! Perfect any time of year. Like our other properties, this home offers comfortable and scenic accommodations, ideal for the bridal party preparing for the big day, family vacations, romantic getaways, or small group retreats. Visit the Naval Academy, Annapolis, Baltimore, Easton, St Michaels, DC, and more. The KI Beach House II home sleeps (8 adults comfortably) max 14 including children or up to 28 if you want to rent this home and the original KI Beach House next door! About a mile from the Blue Heron Public Golf Course.brbrWhat a Retreat! Fish, Eat, Sleep, and Repeat – right here at KI Beach House II by the Marina. Just wait till you see the Captain's Quarters! What a retreat!brbr******brLooking for multiple nearby modern clean beachy homes with nice large yards then let us know because our Kent Island Beach House homes together can accommodate more than 30 of your guests for the perfect getaway, holiday, birthday, work day, or any day! brbrVRBO #351587 KI Beach House accommodations in the heart of the Kentmorr waterfront neighborhood near the Marina, Beach Bar and Grill. Vacation Rentals #3872253 KI Beach House II is a modern-day fisherman's village itself also in the Kentmorr waterfront neighborhood across from the Kentmorr Marina and fishing charter boats side-by-side with our original KI Beach House! All of our locations are conveniently located in Stevensville MD on Kent Island less than 5 miles from the Chesapeake Bay Bridge close to all the destination wedding, golfing, fishing, restaurant, winery, brewery, and shopping hotspots. Go to UTube and check us out - search for Kent Island Beach Housebrbrbr******brAll the modern conveniences and appliances are part of this package: refrigerator, stove, microwave, central air/heat, included linen package, coolers, beach towels and chairs, bikes; built-in hair dryers, ice maker, etcbrbrBook a fishing charter, take a boat ride, enjoy the local fireworks, gaze at the Navy's Flight Demonstration Squadron of Blue Angels, watch the large ships cruise by, walk across the street to the Kentmorr Marina or Beach Bar and Grill, catch a game of golf, take a stroll/bike ride on Kent Island Trail, venture out to the local wineries, or just staycation in the tastefully decorated house or on the oversized wrap around deck overlooking the private beach volleyball court and Chesapeake Bay.brbrCome stay with us today and relax on our deck, one of the local beaches, or just enjoy the house by the Kentmorr Marina and Chesapeake Bay! Kent Island Beach House II: A Fisherman's Village right in Kentmorr is just minutes from Queen Anne’s Silver Swan, Blue Heron Golf Course, The Inn at the Chesapeake Bay Beach Club (Knoxie's Table), Matapeake Park, Romancoke Fishing Pier, Kent Island Resort, Libbey's, the Kent Island Yacht Club, Kent Narrows, Queenstown Outlets, Queenstown Harbor Golf Course, KI Elks, KI American Legion, and more. 20 minutes to Annapolis, 30 minutes to Baltimore, less than 45 minutes to DC, and 2 hours to Ocean City/Rehoboth Beach.brbrQAC has now imposed a 5% hotel tax not just on us but on all short-term rentals that will be added to all future bookings.brbrKeywords: chesapeake bay, eastern shore, kent narrows, rental, stevensville, paradise, wedding, beach, marina, airpark, fishing charter, cruise, fireworks, naval academy, yacht club, dreams, swimming, walking, biking, wildlife, water, trail, golf, new tropical landscaping, private beach volleyball court, kent island, tiki bar, local wineries, shopping, outlets, consignment shops.

5

Bed

2

Bath

14

Sleeps

$537.95

/ Nightly

Private Vacation Home

NEW KI Creek Retreat! 3BR/2bath water view, private house near KI wedding venues

Stevensville, Maryland, United States

Your home away from home while you visit Stevensville/Kent Island! This 7 yr new home and BRAND NEW, as of April 2026, to the short term rental market, features large kitchen, living and dining area with a walk out to large deck overlooking amazing water view (Cox Creek) PLUS screened in porch with 6 person dining table. The house has 3 bedrooms. The master has a king bed (plus a twin sofa bed) and an ensuite bathroom w/heated floors. The two other bedrooms (both with queen beds) share an oversized hall bathroom with plenty of counterspace and mirrors. All bathrooms are equipped with hair dryers, towels, and showers. Full-size laundry washer and dryer with necessities in case your vacation needs fresh clothes. High speed wifi, TVs in living room and each bedroom, and home office workspaces in 2 bedrooms just in case, round out this beautiful home. Maximizing the water view, all the living space of the home is on the second-floor (first level is owner lock-off garage space). There is a handicap accessible chair lift on the stairs, if required (please discuss mobility requirements with host prior to booking). Take a stroll or run down the private road to get some exercise, enjoy nature, and see deer, eagles and foxes in this pristine farm preserve. AC and heating, including a living room gas fireplace, ensure a pleasant stay no matter the season. It's easy to see why you'll be able to unwind at our place and see all the sites and activities on Kent Island, Annapolis, and beyond.brbrImportant Notes: br• The house is at the end of a 1-mile private road which we share with 5 neighbors. Please be respectful of our neighbors with your road traffic. Our rental is limited to a maximum of 4 cars. There is a park-and-ride close by if you need to “stash” additional cars. br• Absolutely no parties or wedding related events.br• Owner lives close by if you need anything.brbrDistances from house:brChesapeake Beach Club 2.8 milesbrKent Island Resort 2.7 milesbrKent Narrows 7.7 milesbrNaval Academy 16.4 miles

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Bath

Sleeps

$331.25

/ Nightly

Agritourism

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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Bath

Sleeps

$565.91

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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

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$755.92

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Private Vacation Home

Kent Island Waterfront | Pool | Stunning View

Stevensville, Maryland, United States

Relax 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: 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.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.brbrBED SIZES:brbrKing - 1 / King - 1 / Queen - 1 / Bunk Bed - Single over Single - 1 / Single Bed - Twin Sized - 1 /

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$351.92

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Private Vacation Home

Chic 3 BR / 2 BA Cottage Near Chesapeake Bay

Stevensville, Maryland, United States

Plan your getaway on the Chesapeake Bay! Blue Heron’s Landing is on beautiful Kent Island, MD. The home is a short walk from scenic waterways and beautiful biking and walking trails, and a quick drive to fantastic dining options and several Maryland’s best wedding venues. This hidden gem is just across the Bay Bridge from Annapolis and 1 hour from DC and Baltimore. It’s the perfect place to disconnect and recharge, or use as a launching point to explore more of Maryland’s Eastern Shore.

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$561.54

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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.

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3

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8

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$206.7

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Apartment

Quiet Waterfront Getaway Private Escape 1BR Apt Retreat with Optional Boat Dock

Stevensville, Maryland, United States

Unplug, unwind, and soak in the serenity at this peaceful waterfront getaway. Tucked away from the noise yet close enough to everything you need, this beautifully appointed 1-bedroom apartment is the perfect escape for couples, solo travelers, or anyone craving a reset by the water.brbrWake up to stunning water views right from your window or outside deck and enjoy your morning coffee as the sun rises over the horizon. In the evening, relax with a glass of wine as the sky reflects across the calm water—pure tranquility.br What You’ll Love:brbrBreathtaking Waterfront Views – Enjoy uninterrupted scenery from the living space brQuiet, Private Setting – Ideal for relaxation, reading, or a romantic retreatbrComfortable 1-Bedroom Layout – Cozy, clean, and thoughtfully designed for your staybrOptional Boat Dock Access – Bring your boat (Fee $30 per day) up to 40' (Depth 3'-6' at dock) or rent one nearby for easy water adventuresbrFully Equipped Kitchen – Cook your own meals or dine out at nearby local favoritesbrFast WiFi + Smart TV – Stay connected or stream your favorites when you want downtimebr Perfect For:brbrWeekend escapesbrRomantic getawaysbrFishing trips & boating enthusiastsbrRemote work with a viewbrbrLocated in a peaceful area with easy access to local shops, restaurants, and outdoor activities, this hidden gem offers the best of both worlds—privacy and convenience.brbr Optional Add-On:brBoat dock access available upon request—perfect for exploring the water right from your doorstep.brbr See Stevensville like a local in this 1-bedroom apartment. Guests will find a peaceful retreat with a lovely living room that includes a comfortable sofa bed. The space stays cozy year-round with heating and air conditioning, making it easy to relax after a day of exploring. A terrific bathroom and thoughtful touches like a hair dryer add to the convenience. Whether you’re unwinding or planning your next adventure, this apartment offers a calm and inviting place to call home. Fall in love with Stevensville and enjoy the magic it has to offer.

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$505.92

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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.

4

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3

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