Vacation Rentals By Owner In Stevensville, MD

$696.92

Chessie Cottage-Chesapeake Bay Great 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

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$978.49

/ 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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Bath

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$836.84

/ Nightly

Private Vacation Home

Private Pool & Stunning Bay Views on Kent Island

Stevensville, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrKent Island Chesapeake Bay Cottage with Private Pool & Sunset Views brbr brbrWelcome to your dreamy poolside getaway! This charming summer cottage offers a private pool and breathtaking views of the Chesapeake Bay. The oversized wrap-around deck is perfect for sipping morning coffee or enjoying stunning Bay sunsets. (Pool is open April through October.) brbr brbrSleeps up to 11 Guests brbr3 Bedrooms • 3 Bathrooms • Ideal for up to 8 adults + 2-3 children brbr brbrMain Floor (Upstairs): brbrKing Suite Bedroom: King bed + En Suite Full Bath brbrTwin Suite Bedroom: 2 Twin beds + En Suite Bath brbrOpen Family Room: Queen Sleeper Sofa + Full-size Daybed brbr brbrLower Level: brbrPrivate Guest Room: Queen Bed + Full Hall Bath brbrSleeping/Family Room: Full Bed + Twin Daybed brbr brbrHighlights: brbrPrivate Backyard Pool (open April 23–October) brbrWrap-Around Deck with Chesapeake Bay Views brbrMultiple Dining Areas: brbrIndoor Dining Table (seats 8) brbrDeck Dining Table (seats 6) brbrPoolside Table (seats 6) brbrFront Yard Table (seats 6) brbrWeber Propane Grill brbrHigh-Speed Internet & WiFi brbr3 Flatscreen TVs brbr3 Bicycles for guest use brbrNASA-developed AquaSpace Water Filter brbrLuxury Linens + Complimentary Toiletries Starter Kit brbrFull Washer & Dryer brbrCircular Driveway Parking for 4–5 Vehicles brbrNote: Home uses window A/C units (no central air) brbrKeyless Entry through garage door keypad brbr brbrLocation: brbrDowntown Annapolis – 19 miles (~25 mins) brbrU.S. Naval Academy – 19 miles brbrWashington, DC – 48 miles brbrBaltimore – 43 miles brbr brbrHouse Rules: brbrMinimum Age: One guest must be at least 25 years old brbrNo Smoking, No Pets, No Parties or Events brbrRespect the home as if it were your own – this is a cherished private residence. brbrPlease be courteous to neighbors and observe quiet hours. brbrCheck-in: 4:00 PM brbrCheck-out: 11:00 AMbrbrExperience the Difference: Professionally Managed by iTrip Annapolis

Bed

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Sleeps

$575.7

/ Nightly

Private Vacation Home

Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly

Stevensville, Maryland, United States

Summary:brEscape to the shores of Kent Island at this 3-bedroom home, just minutes from historic Annapolis and under 2 hours from Washington D.C. and Baltimore. With stunning water views, a private dock, and a fully fenced yard, this home is the perfect setting for family vacations, couples’ getaways, and small group adventures.brbrThe Space:brStart your mornings with coffee on the deck over the bay. Spend your days fishing or crabbing from the dock, exploring Kent Island’s scenic trails, or visiting Annapolis’ charming shops and historic sites. In the evenings, unwind with a glass of wine as boats drift past your backyard.brInside, you’ll find a welcoming open floor plan, comfortable furnishings, and three cozy bedrooms designed for restful nights. The home is stocked with modern conveniences including Wi-Fi, smart TV, and a well-appointed kitchen.brbrWhy Guests Love It:br- Stunning bay views from the deck & living roombr- Private dock for fishing, crabbing, or launching kayaksbr- Fully fenced yard — perfect for pets and outdoor gamesbr- Quick drive to historic Annapolis, local dining, and waterfront activitiesbr- Easy access from Washington D.C. & Baltimore for weekend getawaysbrbrCurated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your waterfront hosts.brbrGuest Access:brKey Coded entryThis property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.brbrThe Neighborhood:brThe property is in a lovely neighborhood, we ask guests to be courteous to our neighbors and the neighborhoods.brbrOther Things to Note:brPet-friendly with a $200 fee per dog (max 2). Starter supply of toilet paper and paper towels provided; please bring extras for longer stays

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$874.5

/ Nightly

Private Vacation Home

Beautiful Kent Island Getaway with Pool

Stevensville, Maryland, United States

PRIME LOCATION! MILE FROM CHEASPEAKE BEACH CLUB. This home offers 4 bedrooms 3 1/2 baths with a bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom on first floor with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front. It's easy to see why you'll be able to unwind at my place.

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$763.2

/ Nightly

Private Vacation Home

Waterfront Escape with Pool Nature Lover Paradise

Stevensville, Maryland, United States

Discover the perfect blend of relaxation and adventure at our stunning waterfront home. With breathtaking water views, a private swimming pool, and plenty of space to unwind, this is the ultimate retreat for families, groups, or anyone seeking a serene getaway.brbrSwin, fish, crab or paddle right from our private beach, cooling off in the pool, or simply soaking in the peaceful surroundings, or take in the sight of wildlife, including bald eagles, blue herons, ospreys, swans, ducks, and more

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Bath

Sleeps

$805.61

/ Nightly

Private Vacation Home

25-50% Off~Private Beach~Hot Tub~Fire Table~

Stevensville, Maryland, United States

Welcome to our Chesapeake Bay Cottage on Kent Island, Maryland! This unique 3 bed 2 bath home with luxurious amenities is a perfect getaway for families or friends looking to create unforgettable memories and experience all the Bay area offers.brbrEscape the hustle and bustle with an easy commute from Annapolis, Washington and Baltimore. The Naval Academy is right across the Chesapeake Bay Bridge. Adventure and relaxation are within easy reach from any mid-Atlantic and northeastern location.brbrWelcome to our Chesapeake Bay Cottage on Kent Island, Maryland! This unique 3 bed 2 bath home with luxurious amenities is a perfect getaway for families or friends looking to create unforgettable memories and experience all the Bay area offers.brbrEscape the hustle and bustle with an easy commute from Annapolis, Washington and Baltimore. The Naval Academy is right across the Chesapeake Bay Bridge. Adventure and relaxation are within easy reach from any mid-Atlantic and northeastern location.brbr~Guest access~brbr- Enjoy the whole house, yard, and beach. brbr- The docks belong to our neighbors, and are not for our guests to use. Please respect their privacy and avoid imposing on them by asking to use their dock.brbr- The two secured closets are for our cleaning team, and the secured shed is for our maintenance team.brbr~Other things to note~brbrLet us know if you'd like to order some fresh Chesapeake steamed crabs. Captain Jimmy is a commercial crabber who lives nearby that we've partnered with to provide crabs fresh from the Bay. He catches bushels of the best and biggest crabs you'll see, and steams them, too! We featured his steamed crabs in our photos. He just needs about 2 days advance notice. You can order by-the-dozen, or by-the-bushel. But ask us for other amounts. Prices are extremely reasonable, they are more than well worth it.brbrThe beach is nice and has good clean sand. At rare times when storms change the bay current the sand may diminish, or be underwater temporarily in high tide hours. But the beach always returns under normal current conditions.brbrOne item to be aware of is the bunk bed. It has a 250 lb. weight limit that is not to be exceeded. Please plan accordingly.brbrWe do not allow pets. But just a few miles north on Kent Island is Dogwood Acres Pet Retreat. They spared no detail in creating the region’s premiere pet lodging and daycare facilities where pets are happy, healthy and engaged. They have excellent online reviews.brbr~Amenities included~brbrScenic views:brbrBay viewbrBeach viewbrbrBathroom:brbrBathtubbrHair dryerbrCleaning productsbrShampoobrBody soapbrHot waterbrbrBedroom and laundry:brbrFree washer – In unitbrFree dryer – In unitbrbrEssentials:brbrTowels, bed sheets, soap, and toilet paperbrbrHangersbrBed linensbrExtra pillows and blanketsbrRoom-darkening shadesbrIronbrDrying rack for clothingbrClothing storage: closet and dresserbrbrEntertainment:brbrEthernet connectionbr65 HDTV with Amazon Prime Video, Apple TV, Disney+, HBO Max, Hulu, Netflix, RokubrbrFamily:brbrPack ’n play/Travel crib - always at the listingbrSheets provided, room-darkening shadesbrChildren’s dinnerwarebrBoard gamesbrHeating and coolingbrCentral air conditioningbrCeiling fansbrPortable fanbrCentral heatingbrbrHome safety:brbrSecurity cameras on property - We have 3 active cameras recording video and audio. One overlooks the front drive, one monitors north side of the home, and a front doorbell camera. A smart home device on the back deck actively records noise decibel levels, but not audio or video. All devices are on the exterior of the home.brbrSmoke alarmbrCarbon monoxide alarmbrFire extinguisherbrFirst aid kitbrbrInternet and office:brbrWifi (500 Mbps)brDedicated workspace - In a common space with a surge protectorbrbrKitchen and dining:brbrKitchenbrSpace where guests can cook their own mealsbrSamsung Stainless Steel refrigeratorbrMicrowavebrCooking basics - Pots and pans, oil, salt and pepperbrDishes and silverware - Bowls, chopsticks, plates, cups, etc.brFreezerbrDishwasherbrSamsung stainless steel electric stovebrSamsung stainless steel single ovenbrHot water kettlebrCoffee maker: drip coffee makerbrWine glassesbrToasterbrBaking sheetbrBlenderbrBarbecue utensils - Grill, charcoal, bamboo skewers/iron skewers, etc.brDining tablebrbrLocation features:brbrWaterfront - Right next to a body of waterbrPrivate beach access - Beachfront - Guests can enjoy a nearby beachbrbrOutdoor:brbrPrivate patiobrPrivate backyard – Not fully fenced: An open space on the property usually covered in grassbrFire pitbrOutdoor furniturebrOutdoor dining areabrPrivate BBQ grill: gasbrbrParking and facilities:brbrFree parking on premisesbrFree street parkingbrPrivate hot tub - available all year, open 24 hoursbrEV charger - level 2, tesla only: 220 volts, 12-35 miles per hourbrSingle level home - No stairs in homebrbrServices:brbrSelf check-inbrKeypad - Check yourself into the home with a door codebrbr

3

Bed

2

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7

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$749.57

/ Nightly

Private Vacation Home

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville, Maryland, United States

Stay comfortably in Stevensville at this 5-bedroom country house. Four king beds and 2 twin bed offer plenty of space for guests to relax. The house features four bathrooms, each with a refreshing shower to start your day right. Enjoy a pleasant atmosphere with heating and air conditioning that keeps the temperature just right. A hair dryer is also available for added convenience. This fabulous country house provides an excellent setting for a memorable getaway. We hope you'll enjoy your stay at our country house.

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$354.77

/ Nightly

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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$999.0

/ Nightly

Private Vacation Home

Waterview Retreat with Beach Volleyball near Marina and Local Wedding Venues

Stevensville, Maryland, United States

Kent Island Beach House LLCbrWelcome to the original Kent Island Beach House offering comfortable water view accommodations for 8 adults, with a maximum occupancy of 14 including children. Stay and Play at the pink house as most people remember it but it is really a coral color. Large yard and Private Beach Volleyball court overlook the Chesapeake Bay located in the waterfront Kentmorr neighborhood.brbrThis expansive almost 1800 sq ft residence boasts tasteful decor across its 4 bedrooms and 3 baths. Instead of 2 stories high just think of it as 2 stories long. brEnjoy the scenic vista from the attached deck, which extends from the open kitchen living area, offering a panoramic view of a private beach volleyball court and the picturesque Chesapeake Bay. Stroll through the serene waterfront neighborhood or simply unwind on our deck while grilling your favorite dishes. The luxurious Master Suite features a spacious King Bedroom with a dedicated workspace and TV, leading to a lavish ensuite equipped with his and hers sinks, a custom tile shower, and a relaxing jetted whirlpool tub. Adjacent is the Starfish Bath, a linen closet, and a 2nd King Bedroom. Journey down the hall to discover the 3rd bedroom, furnished with a King bed AND a California King bed, complemented by a dresser and TV. Additionally, a generously-sized private family room awaits, complete with large screen TVs and a grand fireplace (converted to electric logs in 2025), serving as a 4th bedroom with a daybed & trundle (equivalent to 2 twin beds), along with a full sofa bed, sofa, futon, and recliners. The convenience of the 3rd Pink Bathroom with a shower, adjoining this room, ensures comfort and privacy for guests. brbrWhile not fully ADA handicap compliant, the presence of a ramp at the deck with a sidewalk leading to the back door by the garage renders this home wheelchair and walker accessible.br brPerfect any time of year...Off Season, picture yourself sipping warm hot chocolate by the fire as you enjoy a game of indoor corn hole with your family and friends. In Season, live life to the fullest on the open wrap around deck; just grill and chill; or walk over to the Kentmorr Beach Bar and Grill or the Kentmorr Marina across the street! What a place for meetups or an intimate corporate retreat! Great for families...your children will remember this sandbox forever!brbrThe beds are all made when you arrive. Sheets for the daybed/sofabed/futon are in the hall bath linen closet and spreads are in the big white cooler if needed. 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! 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 home sleeps (8 adults comfortably) max 14 including children or up to 28 if you want to rent this home and the KI Beach House II by the Marina next door! About a mile from the Blue Heron Public Golf Course.brbrFish, Eat, Sleep, and Repeat – right here at the original KI Beach House.brbrbr******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******brbrBook 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, beach, or in the house while the sun sets on the Chesapeake Bay! Kent Island Beach House is just steps away from Kentmorr Marina, Airpark, and Beach Bar and Grill. 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, vacation rentals, 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

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Bath

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$961.26

/ Nightly

Private Vacation Home

Stay by MD's Chesapeake Bay this Father's Day! Walk to Marina & Restaurant.

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.

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Bath

Sleeps

$474.9

/ 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 May 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. Beds freshly made for your stay. 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

3

Bed

2

Bath

8

Sleeps

$230.04

/ Nightly

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.

Bed

Bath

Sleeps

$2142.16

/ Nightly

Private Vacation Home

Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View

Stevensville, Maryland, United States

This short-term rental has an occupancy of 16 individuals with a max. of 12 guests being 18 years or older.brbrExperience spectacular sweeping views of the Chesapeake Bay Bridge from this fully renovated, well-appointed 6-bedroom, 5.5-bath waterfront home, just minutes from downtown Annapolis!brbrThe main level is designed for entertaining, featuring a great room with an open kitchen concept, an oversized island with seating for six, and a cozy seating area. Enjoy meals with family and friends in the light-filled sunroom that comfortably accommodates twelve.brbrDiscover the secret Pirate’s Cave hiding next to the laundry room, a fun-filled game room with a big screen TV equipped with table tennis, darts, air hockey, and foosball—perfect for all-day entertainment with family and friends. The brand new 20x40 swimming pool offers a basketball hoop and a relaxing tanning ledge where you can watch the sun set behind the Bay Bridge. The pool area is adjacent to a covered gazebo deck, an ideal spot for enjoying a crab feast from one of the local restaurants or a glass of wine.brbrThe property also features a new private pier, providing an idyllic setting for crabbing, fishing, and bird watching. Spend tranquil mornings casting a line or catching crabs, and enjoying the serene beauty of local wildlife. The pier offers ample seating for relaxation and is the perfect vantage point for observing the stunning Chesapeake Bay sunsets over the bridge.brbrGather around with drinks on the rear deck outfitted with a gas fire pit and plenty of seating. Or seat around the fire pit in the backyard making smores and watching the night sky. Younger guests will be thrilled by the pirate-inspired treehouse and play area, featuring a climbing wall, pirate plank, swings, slide, hammock, and treehouse!brbrPROPERTY FEATURES:brbrWaterfront: Chesapeake Bay.brPool: 20 x 40 private pool with a basketball hoop. Swimming pools are open from May 22 - October 15. Be sure to bring your own pool towels.brDock: 150 ft x 6 ft private dock for fishing and crabbing.brGame Room: Billiards, ping pong table, air hockey, foosball, and dartsbrOutdoor activities: cornhole, basketball hoops and Tree house.brGrill: Propane grill. Propane is provided.brFireplaces: Outdoor gas fireplace table.brPet Policy: Pets are not permitted.brWiFi: 1000 mpbs, reliably fast (good for 8-10 people or up to 12 devices)

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Bath

Sleeps

$653.66

/ Nightly

Private Vacation Home

Charming 3 Bedroom 3 Bath Beach Front Property

Stevensville, Maryland, United States

This home is situated next to Kent Point Marina at the Southern most tip of Kent Island. If you enjoy crabbing, fishing, boating, kayaking, swimming - it can all be done from this property. You will enjoy panoramic views of the Chesapeake bay from most rooms. Sunrises and sunsets are breathtaking! One of the most visited spots by photographers for the wonderful view of the bay, Bloody Point Bar Lighthouse and the Eagles! Many options for outdoor entertaining areas including your own 350' beach which is shared with one other VRBO family. Central location allows for day trips to DC, Annapolis, Baltimore, & St. Michaels.brbrDine at Knoxie's Table, Harris Crab House, The Narrows, The Fisherman's Inn, The Jetty, Bridges (among many others). Golf at nearby Queenstown Harbor Golf. Bike on the Cross Island Trail. Visit the Chesapeake Bay Environmental Center and Terrapin Park or Mattapeake Beach. Take scenic drives to many exciting areas on the Chesapeake Bay including the US Naval Academy in Annapolis (30 minutes) or the Chesapeake Bay Maritime Museum in St. Michaels. Many outlet stores are also nearby in Queenstown. Fishing and Crabbing Trips may be arranged for an additional fee departing right from your front yard! We can help arrange your crab feast or fish fry upon your return!brbrThe home is ideal for family gatherings. Its layout includes a dining area, living area with 2 Queen sleeper sofas and an outdoor patio overlooking the Chesapeake Bay, a fully stocked kitchen, Master bedroom with Queen bed, large outdoor bay front deck with sofa, and adjoining full bath, 2nd bedroom includes double bed, twin trundle and twin bunk also an adjoining bath, 3rd bedroom includes twin bed with trundle. Laundry room and full bath.

Bed

Bath

Sleeps

$106.0

/ Nightly

Private Vacation Home

Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland

Stevensville, Maryland, United States

Newly renovated 2 story, 3 bedroom, 2.5 bath located on beautiful Thompson Creek, Kent Island, Chesapeake Bay. Spectacular views of the sunset and easy access to crabbing, boating, fishing, 13 miles of bike and hike trails, beautiful beaches, excellent golfing, and several state parks. Space for two vehicles. Kent Island is renowned for its excellent restaurants and bars. Walk to shops and grocery store. Only 20 minutes to Historical Annapolis, and only 50 minutes to DC and to Baltimore. 25 minutes to the BWI airport. Boat slip is included!! Public launch is 5 minutes from the property.

Bed

Bath

Sleeps

$823.9

/ Nightly

Private Vacation Home

Three Decks overlook Marina basin and views of the Chesapeake and Eastern Bays

Stevensville, Maryland, United States

Picturesque views from three decks and 3 bedrooms; additional 3 bedrooms. Walk to beach, large entertaining room with pool table, bar, and poker table, mini indoor basketball, walking distance to marina with fresh caught in seasonal seafood available

Bed

Bath

Sleeps

$298.81

/ Nightly

Private Vacation Home

Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville, Maryland, United States

Enjoy your vacation in this Stylish Coastal-Country Home with 3 acres of outdoor living! Perfect for Families & Weddings!brbrWe are conveniently located to many areas/cities:brAnnapolis- 15 milesbrBaltimore- 40brWashington DC- 45brEaston- 30brbrEnjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions.brbrThis is a Non-Smoking House. Also No Pets or Parties and 14 max guests (8 max adults).brbrBook Today!brbrThe Space:brbrThis 3 acre Home with Private Pond on property, is located in Stevensville/Kent Island has a quiet & peaceful setting at the end of a cul-de-sac.brbrThe first floor has the Kitchen, Living Room with a large sectional sofa, a Full Bathroom, a Sauna w/Shower, the Master Bedroom with King Bed, and the 2nd Bedroom with Queen Bed.brbrLocated on the upper level is a Bedroom/Loft Area that sleeps 6 with 2 Full-Sized Beds and a Full Pullout Sofa. Upper level also has a 2nd Master Bedroom with a King-Size Bed and Full Bathroom.brbrThere are Smart TV's with streaming services in the living room and Master Bedroom. The House also has WIFI, A/C, Heating, Washer/Dryer, Microwave, Dishwasher, Coffee Maker, Kitchen Supplies, etc.brbrBlankets, pillows, linens and bath towels ARE provided with the home.brbrThe Kitchen is equipped with cookware and essentials for all your cooking needs.brbrGuest Access:brbrYou will have full access to the entire house and property, with the exception of the garage, and exterior buildings.brbrOther Things to Note:brbr- The home is two stories with necessity to climb a few stairs to access the entry and a set of stairs to access the upper floor inside. However there are 2 bedrooms, including the master, on the first floor. brbr- Also, there is a private workshop on the property that houses businesses that may be active during normal business hours.brbr- The Waterfront & Lakeview description refers to the Private Pond that is located directly on the property.brbr- Per county regulations, there is a maximum of 8 adults (18 years or older) allowed to stay over at the property.

Bed

Bath

Sleeps

$305.12

/ Nightly

Private Vacation Home

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville, Maryland, United States

Enjoy your vacation in this Stylish 4 Bedroom Home with a view of the Chesapeake Bay from living room and kitchen! Perfect for Families & sleeps 11.brbrWe are conveniently located to many areas/cities:brAnnapolis- 20 milesbrBaltimore- 45brWashington DC- 50brEaston- 35brbrEnjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions.brbrThis is a Non-Smoking House. Also No Pets or Parties and 11 max guests (8 max adults).brbrBook Today!brbrThe Space:brbrThis 4 bedroom Home is located in Stevensville/Kent Island in a quiet residential Community and is only a short walk away from the Chesapeake Bay. The main living room is on the entry level which has a sleeper sofa.brbrLocated on the upper level is the Kitchen, upper outdoor deck, the Master Bedroom with King-Size Bed, the second bedroom with Queen Bed and the third bedroom with a bunk bed (guests sleep on Bunk Bed at their own risk) and underneath trundle - all singles.brbrOn the lower level is an additional bedroom with sleeper sectional pull-out sofa, laundry room and half-bath.brbrThere are Smart TV's with streaming services in both living rooms and Master Bedroom. The House also has WIFI, A/C, Heating, Washer/Dryer, Microwave, Dishwasher, Coffee Maker, Kitchen Supplies, etc.brbrBlankets, pillows, linens and bath towels ARE provided with the home.brbrThe Kitchen is equipped with cookware and essentials for all your cooking needs.brbrGuest Access:brbrYou will have full access to the entire house and property, with the exception of the garage, exterior buildings and a supply closet downstairs.brbrOther Items to Note:brbr- The home is a split level with necessity to climb a number of stairs to access the front door and the upper and lower floor inside.brbr- The house is located in a quiet Residential Community and the HOA has set a STRICT quiet hours time from 10 PM to 7 AM. Please respect the surrounding neighbors as any violations could result in involvement of local authorities and immediate cancelation of the reservation without refund.brbr- The neighbor to the right when looking at the house from the street, prefers their privacy and kindly asks not to be interacted with. Thank you.brbr- There is enough parking in the driveway for 5 vehicles, no street parking.brbr- Per county regulations, there is a maximum of 8 adults (18 years or older) allowed to stay over at the property.

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Bath

Sleeps

$1489.21

/ Nightly

Private Vacation Home

Stevensville, Maryland, United States

Relax and unwind at this spa-like luxury waterfront estate. Located on the Chesapeake Bay, this newly constructed vacation rental features 5 bedrooms, 5 bathrooms, and opulent interior design with expansive living areas. brbrAre you looking to entertain You have come to the right place. Wow your guests with the cuisine you will craft in the chef-inspired kitchen that boasts stainless-steel appliances, an enormous kitchen island and serve them at the grand dining table with panoramic sunset views.brbrAfter dinner you and your guests can enjoy the pool or hot tub while sipping cocktails and talking about how you never want to leave. brbrNatural lighting creates the perfect ambiance in any of the 5 private suites. Each suite also offers its own ensuite. 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. brbrBe prepared to have your breath taken away. Book your luxury getaway today!brbrPROPERTY FEATURES:brbrWaterfront: Chesapeake BaybrDock: Private dock with power and water available for guest use.brPool: Private pool. Swimming pools are open from May 15 - October 15. brHot Tub: Hot Tub available for guest use from May 15 - October 15.brFirepit: Propane provided.brElevator: Available for guest use.brWiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.brbrTHIS IS A LUXURY RENTAL:brbrGuests that stay at one of our luxury rentals unlock private access to a world of privilege. Benefits include:brbrUpon request an ESVR representative greeting at your arrival. They will ensure the rental meets our white glove standard, provide a tour of the property and answer any questions.brbrUpgraded essentials package to include: paper towels, trash bags, toilet paper per bathroom, dishwasher pods, laundry pods, and full size (soap, shampoo and conditioner) per bathroom for your entire stay.brbrAccess to our proprietary app (A Day With ESVR) for guests that provides guests access to curated maps featuring all of the best places and experiences Maryland’s Eastern Shore has to offer.brbrAccess to our dynamic and fully integrated mobile-first welcome book designed to delight and support guests with property information and direct messaging with a guest service representative throughout your stay.brbrAccess to our concierge services to help with booking nearby activities, tours and more.

5

Bed

5

Bath

10

Sleeps

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