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House vacation rentals in Assateague Island

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Top-rated house rentals in Assateague Island

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Guest favorite
Home in Chincoteague

Dragonfli Bay House on Chincoteague Island

Relax in this calm, stylish space. This home has been lovingly refreshed by its current owners. Every detail has been considered. Inside you will find well appointed rooms designed for function and comfort. Outside, tranquility awaits you. Enjoy morning coffee overlooking the water, kayaking on the bay, end the day relaxing by the fire. Head to Assateague to swim, surf fish or hike to the famed lighthouse. Return with the day's catch to utilize the fish cleaning station and outdoor shower.

4.94 out of 5 average rating, 159 reviews
Top guest favorite
Home in Chincoteague

Island House: Kayaks, Bikes, Beach Gear & Firepit

Welcome to Happy Ours! Relax with the whole family at this peaceful Chincoteague home. Walk to the park (Pony Swim!). This beachy cottage offers all the charm with plenty of space, in a quiet area with a huge property. This is a family home that we enjoy with friends & family year-round. We would love to share that experience with you! If we can do anything to make your stay more enjoyable, don’t hesitate to reach out, and please kick back and relax and enjoy all that Chincoteague has to offer!

4.96 out of 5 average rating, 108 reviews
Top guest favorite
The exterior of the home is showcased with a well-maintained lawn, framed by flowering shrubs. A welcoming front porch is visible, featuring two wooden benches. The entrance is highlighted by a maroon door, accompanied by classic shutters on the windows.
Home in Parsonsburg

Charming Home in a Neighborhood

Our home is well loved and is a great place to spend some quality family time. It is close to the Salisbury Airport (SBY), Salisbury University (SU), Perdue Stadium (Delmarva Shorebirds) and short drives to University of Maryland Eastern Shore (UMES), the beaches in Ocean City MD, Asseteauge Island, Md and some Delaware beaches too. Winterplace Equestrian Park is within 4 miles and Pemberton Historical Park is just across town. Price includes parking in the attached oversized 2 car garage.

4.99 out of 5 average rating, 175 reviews
Top guest favorite
A coastal retreat is presented in a light-colored two-story home elevated on stilts. A set of steps leads to a covered porch with a railing. A small seating area with yellow chairs is visible beneath the porch. Lush green trees surround the property.
Home in Chincoteague

Pearl in the Pines: bikes, kayaks, EV charger

Nestled in the shade of tall pine trees in the private community of Oyster Bay, "Pearl in the Pines" is a charming coastal retreat equipped to meet any need. This bright and beachy 3-bedroom, 2-bathroom home accommodates up to 6 guests and is pet-friendly, making it an ideal space to vacation with your entire family. The spacious screened porch offers the perfect perch to savor your morning coffee with the sunrise or relax with friends and family while enjoying fresh, locally sourced seafood.

4.98 out of 5 average rating, 121 reviews
Guest favorite
A living room features light blue seating arranged around a coffee table, complemented by a decorative cabinet and a large television. Natural light filters through the window, enhancing the tranquility of the space, which is accented by a ceiling fan and wall art above the entrance.
Home in Selbyville

Central Haven with Great Fenced Yard

You will be close to everything when you stay in this centrally-located home. The rear deck and grill are great for enjoying time outside. There's a fenced rear yard, making this home a perfect choice for man's best friend. We welcome dogs of any breed, size, and weight. We do offer size-specific pet amenities, so please share a photo of your dog when booking, or provide a basic description so we can set out appropriate amenities. For those traveling with cats, please inquire before booking.

4.94 out of 5 average rating, 172 reviews
Top guest favorite
A green pasture is featured, where a group of five horses graze peacefully. The background showcases a wooded area with tall trees, under a clear blue sky. A small shelter is visible in the distance, complementing the tranquil rural setting.
Home in Accomac

Heartsong Farmhouse , a nature lover's retreat.

Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

4.98 out of 5 average rating, 307 reviews
Guest favorite
A waterfront backyard features sandy areas lined with a white picket fence. A picnic table is positioned on the beach, facing the calm waterway. Houses are visible along the banks, framed by trees and distant structures under a soft evening sky.
Home in Ocean Pines

Waterfront Beach Home in the Ocean City, MD Area

There is room for 8 adults (plus 2 kids). Located in the premiere seaside community in the Ocean City area, Ocean Pines, this wonderful waterfront home provides amazing views both day and night. The open floor plan provides guests with lots of room to socialize and bond, but also has secluded bedrooms that provides needed privacy. The outdoor living area is to die for. Sit back and watch the sun set over the canal while you catch up with friends or loved one. Use our bikes!

4.91 out of 5 average rating, 211 reviews
Top guest favorite
A light-filled living room is presented with soft beige seating arranged around a round, patterned coffee table. A landscape artwork adorns the wall above the couch. Natural light streams through a nearby window, highlighting a plant tucked in the corner.
Home in Chincoteague

Adorable Beach Cottage Just Steps From Town & Bay

Escape to Wiggle Bay, a darling 1955 2 BR sunny cottage nestled in the heart of "one of the most beautiful, charming small towns in Virginia." Enjoy a bay breeze on the screened front porch--heaven! Perfectly located on a quiet street, just steps from local shops, a coffee house, and the waterfront park, where you can watch the boats, enjoy the sunset and feed the ducks. Just 2.3 mi to Assateague Seashore/Chincoteague Refuge. Ideal for a peaceful and convenient getaway!

4.94 out of 5 average rating, 208 reviews
Top guest favorite
The front of the house is framed by a large tree, with a pathway leading to the entrance. The porch features a bench for seating, and greenery surrounds the property, creating a welcoming outdoor setting.
Home in Onancock

Egret’s Point on the Creek

Egrets Point on the Creek, is a beautiful and peaceful place to relax and plan your Eastern Shore exploration. Whether you are enjoying the fire pit by the creek, or taking a nap in the hammocks, canoeing, walking or exploring historic Onancock, life by the creek is sweet. Chincoteague to the north, Cape Charles to the south. Excitement abounds. Coastal exploration, boating, fishing, fine dining, artisan shops, art galleries, farmers markets and sandy beaches. Come and enjoy!

5.0 out of 5 average rating, 118 reviews
Top guest favorite
The backyard features a well-maintained putting green, with white flags marking the holes. A spacious home with a covered patio and landscaped garden is visible in the background, surrounded by lush greenery and trees.
Home in Berlin

Assateague, Golf, Ocean City, all Within Minutes!

Worcester Co. Lic. #859 PLEASE NOTE: number of allowed guests: No more than 8 golfers. (Min age 25) No more than 10 adults. (Min age 25) Related families up to 12 guests. We do NOT rent to high school senior groups. Please note, we own the white house next to our STR. Occasionally you may see us there, however, we are committed to your comfort & privacy. Located 1.5 miles from Assateague Island beaches. 3 courses within .5 miles. Towels and linens for every guest.

4.98 out of 5 average rating, 105 reviews
Top guest favorite
A barn-style exterior of the condo is showcased, featuring a metal roof and three large garage doors at ground level. The second floor includes a deck with an entrance door. Expansive green space surrounds the property, with trees visible in the background under a clear blue sky.
Home in Berlin

SpaciousCondo nearOcean City|Winery|Golf on 5Acres

Come stay in our 2nd Floor Condo on our private 5-Acre Property! Enjoy the Barn-Like look from the outside, but inside, find a modern & spacious condo with a fully-equipped kitchen. Located in Berlin, Maryland, you are minutes to Historic Berlin and only 15 minutes to all the fun that Ocean City, Maryland has to offer! Have your morning coffee on the deck and soak in the scenic views or pitch a tent, light up the fire pit, let the kids run wild! We'll see you soon!

4.96 out of 5 average rating, 120 reviews
Top guest favorite
A cozy living area presents a light brown couch adorned with colorful cushions and a decorative throw. Two accent chairs sit across from the couch, positioned on a patterned area rug. Natural light filters through sheer curtains covering a large window, illuminating the space.
Home in Ocean Pines

Sweet Retreat

Sweet Retreat is conveniently located in Ocean Pines, Maryland. The premiere residential and resort community of Ocean Pines is located eight miles inland from the ocean resort town of Ocean City. Ocean Pines has over 9 miles of waterfront property and 3,000 acres of wooded areas. Community amenities include beaches, a yacht club, golf course, community center, a Beach Club Pool and other community pools. Passes are available at ocean Pines Association.

4.97 out of 5 average rating, 115 reviews

Popular amenities for Assateague Island house rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
A serene view of Sinepuxent Bay stretches across the horizon, showcasing expansive grasslands and soft green vegetation. The sky transitions to warm hues of sunset, creating a calming atmosphere. A glimpse of the fishing pier is visible in the distance, enhancing the waterfront scenery.
Home in Berlin

Mosaic Life Escapes -Bayfront Million Dollar Views

4.81 out of 5 average rating, 122 reviews
Top guest favorite
The exterior of a single-story house is visible, featuring a spacious front porch with white railings. Large windows allow natural light to enter, while a driveway provides parking for two vehicles. A wooded area surrounds the property, enhancing its peaceful setting.
Home in Ocean Pines

Camelot

4.97 out of 5 average rating, 152 reviews
Top guest favorite
A spacious living room features a comfortable dark sofa, two brown chairs, and a cozy fireplace. Natural light enters through large windows adorned with light blue drapes. A ceiling fan and recessed lighting contribute to a bright and airy atmosphere, complemented by modern decor.
Home in Ocean Pines

Ocean Pines Retreat with Beach Club

4.99 out of 5 average rating, 135 reviews
Guest favorite
A light and airy deck features a rectangular dining table surrounded by aqua-colored chairs. A calm water view is visible beyond the railing, with flags gently waving in the breeze. Soft lighting is provided by string lights overhead, enhancing the inviting atmosphere.
Home in Ocean City

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

4.94 out of 5 average rating, 288 reviews
Top guest favorite
A modern kitchen is showcased with sleek dark cabinets and a white countertop. A pendant light hangs above, illuminating the space. An open layout allows views into the adjoining living area, which features warm wood tones and natural light from large windows.
Home in Chincoteague

Seas the Day Getaway ~ Pool ~ ONLY 3 mi to BEACH

4.96 out of 5 average rating, 456 reviews
Guest favorite
A bright living area features a comfortable blue sofa and a cozy armchair, with a gas fireplace as the focal point. Natural light floods the space through large windows, while a dining table and chairs are visible in the background, creating an inviting atmosphere for gatherings.
Home in Ocean Pines

Tortuga Cottage: Your All- Season Getaway

4.88 out of 5 average rating, 168 reviews
Guest favorite
A back deck features a seating area composed of a sofa and ottoman with soft cushions, facing a calm canal. A wooden table is positioned nearby. A red umbrella is closed and stands beside the seating, while a sunset casts gentle hues across the water.
Home in Ocean City

3 BR Waterfront Home, Minutes to the Beach

4.93 out of 5 average rating, 150 reviews
Guest favorite
A serene canal view captures waterfront homes reflecting in calm waters at sunset. Docked boats and lush trees frame the scene, showcasing the tranquil atmosphere of the eastern shore. The clear sky hints at the day's end, lending a peaceful ambiance to the surroundings.
Home in Greenbackville

Bayfront Modern Retreat • Dock, Kayaks, Views

4.91 out of 5 average rating, 133 reviews

Weekly house rentals

Top guest favorite
A cozy living area features a light gray sofa adorned with decorative pillows and a small blue ottoman. Natural light brightens the space, showcasing art on the walls and a dining area in the background, complemented by a wooden table and chairs.
Home in Ocean Pines

Home Away from Home , Pet friendly retreat

4.87 out of 5 average rating, 107 reviews
Top guest favorite
A one-story white house is surrounded by a green lawn and is enclosed by a fence. The home features a peaked roof and small front porch, with large windows allowing natural light. A decorative sign is positioned in front, marking the property.
Home in Tangier

Island Oasis, Tangier Island, Virginia

5.0 out of 5 average rating, 167 reviews
Top guest favorite
A modern kitchen and dining area feature light-colored cabinetry and stainless steel appliances. A large wooden dining table accommodates eight, surrounded by aqua-colored chairs. Natural light filters through the window, enlivening the space, while a decorative pendant light adds character above the table.
Home in Chincoteague Island

Rest A'Shored charming Chincoteague getaway

4.92 out of 5 average rating, 218 reviews
Guest favorite
Home in TYLERTON

3 bedroom/2.5 bath Smith Island bungalow with dock

4.95 out of 5 average rating, 152 reviews
Superhost
A cozy living area features a leather armchair positioned next to a small side table with a lamp. A storage chest rests on the floor beneath a collection of framed artworks and a flat-screen television, enhancing the eclectic atmosphere of the space.
Home in Berlin

Joy in the Morning @ Berlin Boho Bungalow

4.81 out of 5 average rating, 155 reviews
Guest favorite
A spacious family room showcases a large sectional couch in a neutral tone, complemented by decorative pillows. A TV is mounted on the wall above a modern fireplace, with natural light filtering through the window blinds.
Home in Chincoteague

Chincoteague Island Creekside Cottage

4.9 out of 5 average rating, 122 reviews
Top guest favorite
Home in Chincoteague

New house, Bay views, 4 Beds, Game room

5.0 out of 5 average rating, 22 reviews
Top guest favorite
A hot tub is situated on a wooden deck, bubbles rising gently from the water's surface. The vibrant blue exterior of the house is contrasted by pink trim. Sunlight reflects off the hot tub, creating a bright and inviting ambiance. A screened porch and balcony are visible in the background.
Home in Chincoteague

Hot Tub. Fire pit. Fenced Yard. Games. Downtown.

4.98 out of 5 average rating, 56 reviews

Private house rentals

Guest favorite
A cozy seating area is positioned on the waterfront, featuring plush cushions and decorative pillows. Two lanterns with candles add ambiance. Lush greenery and a clear sky are visible in the background, enhancing the serene view of the water.
Home in Berlin

Private pool, waterfront, kayaks, bikes, firepits!

4.97 out of 5 average rating, 86 reviews
Top guest favorite
A serene sunset is captured over the water, with the sun gently descending on the horizon. Silhouette of dock pilings is visible against the shimmering surface of the water. Tall grasses in the foreground reflect warm hues of orange and pink, enhancing the tranquil scene.
Home in Chincoteague

Waterfront-Views from all rooms-CI bay sunset

4.98 out of 5 average rating, 98 reviews
Guest favorite
Home in Saxis

Marsh View Saxis

4.93 out of 5 average rating, 74 reviews
Guest favorite
Home in Berlin

That South Point Joint - Assateague/Golf/Boat Ramp

4.8 out of 5 average rating, 5 reviews
Top guest favorite
A spacious living area features a large sectional couch and a coffee table, surrounded by wooden flooring. A world map adorns the wall, and natural light streams in through the windows. The open layout flows into a dining area visible in the background.
Home in Chincoteague

The Magnolia House ~Available this weekend ~

5.0 out of 5 average rating, 53 reviews
Guest favorite
A charming house with a light blue exterior is surrounded by lush greenery. A spacious deck features potted plants and outdoor seating. Colorful Adirondack chairs in red and blue are placed around a small fire pit on a patterned stone patio, inviting relaxation.
Home in Ocean Pines

Cozy beach home away from home!

4.95 out of 5 average rating, 21 reviews
Top guest favorite
A large wooden deck features several adirondack chairs positioned to face expansive views of the marshland and water. A clear blue sky complements the serene landscape, with gentle clouds casting soft shadows over the scene.
Home in Parksley

Serene Waterfront Metompkin Retreat - Entire Home

5.0 out of 5 average rating, 24 reviews
Top guest favorite
A spacious living room features a large brown sectional sofa adorned with colorful throw pillows. A round coffee table sits in the center, surrounded by a light-colored woven rug. Natural light floods the space from multiple windows, highlighting the decorative wall mirrors and neutral tones.
Home in Berlin

Cottage on Snug Harbor, hot tub, private backyard!

5.0 out of 5 average rating, 44 reviews