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Vacation rentals in Assateague Island

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Top-rated vacation rentals in Assateague Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A cozy cottage exterior is presented with a light blue façade and a welcoming front porch. The entrance features a small overhang and steps leading to the front door, accompanied by neatly trimmed bushes and a well-maintained lawn under clear blue skies.
Cottage in Chincoteague

Maggie’s Cottage on Poplar - Our Happy Place!

Step back in time and enjoy the simplicity of this 2 bedroom, 1 bath vintage Chincoteague cottage located in the heart of town. Quaint, quiet and cozy - Maggie’s Cottage is the perfect retreat to slow down, relax, and enjoy an island get away... anytime of the year! Maggie’s Cottage is just right for a couples get away, girls trip, a solo retreat, or a small family vacation. Well stocked and comfortable- you will feel right at home. Walking distance to local dining, shopping and waterfront!🐴🦪🌅

4.94 out of 5 average rating, 209 reviews
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
Guest suite in Ocean Pines

Stunning private waterfront suite

Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!

4.95 out of 5 average rating, 421 reviews
Top guest favorite
Adirondack chairs are arranged in a semicircle facing a stunning sunset over Chincoteague Bay. The sky reflects hues of orange and pink, while the calm waters mirror the colors above. A firepit is positioned nearby, surrounded by tall grasses.
Cottage in Chincoteague

Waterfront-CI Bay sunsets-Amazing views

Wide expansive waterfront view of Chincoteague bay-awesome sunsets! 5 waterview rooms. The narrow bit of land across 3446 Main St. belongs to our property w/chairs + a firepit + water access to launch kayaks (2) provided! An open plan-coastal rustic design. Front sitting room w/sofa + high-top table. A large upscale kitchen, two sofas in living room, 2 bdrms, & sleeping loft + a tiny office with a twin murphy bed. Large deck-table, sofa + grill. Family home, not ideal for more than 3 adults.

4.96 out of 5 average rating, 170 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, 207 reviews
Guest favorite
A spacious houseboat is docked securely along the water's edge, featuring large windows and a deck area. The surroundings include trees and a sandy space, creating a coastal atmosphere. The sky displays soft clouds illuminated by the setting sun.
Houseboat in Snow Hill

"Jolly"- Houseboat Getaway

"Tiny house on the water"! Jolly is a 42ft Holiday Mansion. Baywater Landing buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & deck areas to enjoy! 35 mins from Ocean City & Assateague Island. 45 mins from Chincoteague Island. Jolly remains docked, but guests have access to kayaks and paddle boards at no additional charge. Baywater Landing is secluded- some even say "boring"- but we think that's the whole point!

4.87 out of 5 average rating, 181 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
Guest favorite
A cozy bedroom features a white, wooden bed frame with a floral-patterned coverlet. Two pillows and a decorative cushion rest against the headboard. A bedside table holds a lamp, and natural light enters through a window with soft curtains.
Guest suite in Chincoteague

Baywatch North-Waterfront & Roaming Ponies

Lovely space! 2 bedroom/1 bath vacation efficiency, decorated with coastal charm, each with a door to the outside. Make-shift kitchen with microwave, small fridge, stoked Keuring coffee and tea bar, shared patio cooking area, bbq grill, fantastic view, beach items, plenty of parking, very quiet, out of the way of everything, super laid back host living in the other portion of the house. There is no living room. Labradors and cats on premises, ponies too!

4.94 out of 5 average rating, 359 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
Top guest favorite
A wooden dock extends over calm water, surrounded by tall trees. A pair of Adirondack chairs provide a peaceful spot to enjoy morning sunlight filtering through leaves, creating a serene atmosphere perfect for relaxation.
Home in Newark

Secluded Waterfront - Beach 15mi, Kayaks, Firepit

Casa Blue Heron is a 2,254 ft² (209 m²) custom waterfront home with a private dock, firepit, and water views throughout - nestled on a tidal inlet connected to Chincoteague Bay - and near Assateague, Berlin, Ocean City, Snow Hill, and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature… Wish I had booked an extra day!" Add us to your wish list by clicking the ❤️ in the upper-right corner.

5.0 out of 5 average rating, 125 reviews
Guest favorite
A modern kitchen is presented with white cabinetry and stainless-steel appliances, featuring a refrigerator, microwave, and coffee maker. A dining table is set for four, and a cozy seating area with a blue couch is visible. Natural light enters through a window, enhancing the space.
Cottage in Chincoteague

Key Lime Cottage

Escape to your own bayfront retreat in Chincoteague Island, Virginia. Our Key Lime Cottage at the Key West Cottages resort offers views of the Chincoteague Bay, giving you a front-row seat to the breathtaking sunsets that Chincoteague offers each night. This one-bedroom private cottage includes a master bedroom with two queen beds, a fully equipped kitchen, living and dining space, waterfront deck and access to many amenities!

4.94 out of 5 average rating, 130 reviews
Top guest favorite
An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.
Cottage in Westover

Rumbley Cottage on the Tangier Sound-Private Beach

Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. Many amenities: WE PROVIDE THE FIREWOOD AND STARTERS, kayaks, paddle boards, MB toiletries.

4.99 out of 5 average rating, 264 reviews

Popular amenities for Assateague Island vacation rentals

BeachfrontSelf check-inFree parking on premisesGymBBQ grill

Assateague Island beach vacation rentals

Top guest favorite
A vibrant neon sign reading 'Sea Glass Sunrise' is framed by lush green foliage, set against a backdrop of a serene beach at dawn. The soft pastel colors of the sky create a peaceful atmosphere, enhancing the welcoming ambiance of the space.
Condo in Ocean City

Gorgeous Beachfront! King Bed, Direct Ocean View!

4.99 out of 5 average rating, 149 reviews
Guest favorite
Condo in Ocean City

One Bedroom Beachfront Apartment Mid-Town

4.89 out of 5 average rating, 132 reviews
Guest favorite
A cozy guest suite is presented, featuring a spacious bed covered with a vibrant blue blanket. Decorative elements include a light-colored rug and a plant next to the bed. A small bookshelf and artwork adorn the walls, contributing to the room's inviting decor.
Guest suite in Fenwick Island

Sea Dunes King Suite, Exclusive Private Beach - DOG FRIENDLY!

4.83 out of 5 average rating, 133 reviews
Guest favorite
A wooden boardwalk leads to a charming beach cottage, flanked by sandy beach and lush greenery. The cottage features large front steps, a light-colored exterior, and multiple windows offering views of the surroundings. The peaceful shoreline setting enhances the inviting entrance.
Cottage in Deal Island

Private Beachfront Cottage with 2 Bedrooms + Loft

4.94 out of 5 average rating, 99 reviews
Top guest favorite
An open-concept living area showcases a spacious sofa arranged around a light-colored coffee table, accented with decorative shells. A dining area with white bar stools and a fully equipped kitchen are visible in the background, along with coastal-themed decor and soft natural light.
Condo in Ocean City

Oceanside Charm, desirable midtown Ocean City, MD

4.98 out of 5 average rating, 119 reviews
Top guest favorite
A private balcony features a high table with two chairs, providing an unobstructed view of the ocean and beach below. The scene is enhanced by the bright blue sky and gentle waves, creating an inviting spot for enjoying morning coffee.
Condo in Ocean City

Beautiful Renovated Ocean Front Condo 1b/1.5ba

4.99 out of 5 average rating, 161 reviews
Guest favorite
A spacious deck offers breathtaking views of the water at sunset, with a stunning orange and pink sky. Four Adirondack chairs are arranged around a brown wicker coffee table, complemented by striped cushions. The serene water reflects the evening sky, creating a tranquil atmosphere.
Cottage in Onancock

A "True" Chesapeake Bay Waterfront Experience!

4.94 out of 5 average rating, 191 reviews
Guest favorite
A serene ocean view is presented from a private balcony, featuring two teal chairs. The sandy beach stretches into the distance, with gentle waves lapping at the shore. A clear sky completes the tranquil coastal scene, creating a peaceful atmosphere.
Condo in Ocean City

Oceanfront Paradise | Pool | Hot Tub | Beach

4.92 out of 5 average rating, 290 reviews

Assateague Island house rentals

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

4.98 out of 5 average rating, 121 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

4.96 out of 5 average rating, 120 reviews
Top guest favorite
Home in Chincoteague

Island House: Kayaks, Bikes, Beach Gear & Firepit

4.96 out of 5 average rating, 108 reviews
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 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.

4.98 out of 5 average rating, 307 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

4.99 out of 5 average rating, 175 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
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

Assateague Island condo rentals

Top guest favorite
A panoramic view of the ocean is visible, with gentle waves lapping at the sandy beach. Below, an outdoor pool is surrounded by lounge chairs and clear pathways, providing a peaceful atmosphere. Skies are blue, enhancing the serene coastal setting.
Condo in Ocean City

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

4.88 out of 5 average rating, 142 reviews
Top guest favorite
A cozy living area displays a light blue color scheme. A white sofa is positioned beside a coffee table on a patterned rug, while a dining table is set nearby. Floor-to-ceiling sliding doors open to a balcony, offering views of the ocean.
Condo in Ocean City

Caramar Couples Retreat

4.96 out of 5 average rating, 322 reviews
Top guest favorite
Condo in Ocean City

Ocean Side 1BR / 1.5BA Renovated Modern Condo

4.96 out of 5 average rating, 190 reviews
Guest favorite
A pair of blue Adirondack chairs are positioned at a small table on a balcony overlooking the ocean. The expansive view of the sandy beach and distant umbrellas is visible, creating a serene spot for relaxation.
Condo in Ocean City

Luxury Oceanfront Escape!

4.96 out of 5 average rating, 239 reviews
Top guest favorite
The living area is spacious, featuring a light blue wall color and a large sectional sofa. Natural light floods through windows, illuminating the decorative rug. The outdoor porch includes dining furniture and offers views of the canal and neighboring buildings.
Condo in Ocean City

Beautiful waterview 2B condo w/Dock&Close to Beach

5.0 out of 5 average rating, 120 reviews
Top guest favorite
A serene waterfront scene is captured at sunset, with vibrant colors reflected in the calm water. A charming building with large windows is illuminated, surrounded by lush trees, and boats are docked along the waterfront, creating a peaceful atmosphere.
Condo in Ocean Pines

Water view at Ocean Pines Yacht Club Condo

4.97 out of 5 average rating, 224 reviews
Guest favorite
A modern kitchen is complemented by a spacious dining area and cozy living room with ocean views. White cabinetry and stainless steel appliances enhance the kitchen, while large windows allow natural light to fill the space, highlighting the wood-paneled ceiling.
Condo in Ocean City

Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool

4.95 out of 5 average rating, 187 reviews
Guest favorite
An enclosed patio provides a direct view of the ocean, with sandy beach and water visible beyond a railing. Comfortable seating options are arranged with a small table, allowing for relaxation while enjoying the ocean scenery.
Condo in Ocean City

Direct Oceanfront close to Northside Park!

4.98 out of 5 average rating, 260 reviews

Frequently Asked Questions

  • Where is Assateague Island located?

    Assateague Island stretches along the coasts of Maryland and Virginia on the eastern shore of the United States. It is known for its sandy beaches, coastal marshes, and the habitat it provides for wild horses.

  • When is the best time to visit Assateague Island?

    Late spring and early autumn are frequently suggested for a visit to Assateague Island, with mild temperatures and lighter crowds. Many visitors enjoy summer for swimming and camping, though wild ponies and migratory birds draw interest year-round.

  • What are some things to do near Assateague Island?

    Around Assateague Island, you can explore walking trails, sandy beaches, and canoe routes, or observe the wild ponies and local birdlife. The area also has opportunities for crabbing, kayaking, and learning about coastal ecology at visitor centers.

  • How is the weather near Assateague Island?

    Assateague Island experiences mild winters around 29–51°F (-1–10°C) and warm, humid summers, with July highs reaching 86°F (30°C). Spring and autumn are often suggested for comfortable temperatures and fewer crowds, though occasional rain can be expected throughout the year.