Vacation rentals in Assateague Island

4.94 out of 5 average rating, 108 reviews

Dragonfli Bay House - Newly Renovated Home

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, kayak on Oyster 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.

4.89 out of 5 average rating, 283 reviews

Tiny home in Snow Hill

Private cottage and gardens/comfortable queen bed.

Private cottage and gardens, comfortable Queen bed, full bath and kitchenette, within walking distance to historic Snow Hill. 30 min. drive to Ocean city and Assateague Island National park. This cottage was once a old school woodworking shop which is now on display at the old iron furnace town museum nearby. This beautiful three hundred year old town sits on the beautiful Pocomoke river with canoe, kayak, and bike rentals. Museums, art galleries, speciality shops, food and entertainment.

4.97 out of 5 average rating, 165 reviews

Charming Island Home "Sandy Pines"

Come and enjoy a nice, relaxing vacation at this charming island home. "Sandy Pines" lies just a half a block from the water and a block and a half from the bridge to Assateague (where the beach is). The downstairs features a living room and dining room, 2 bedrooms (equipped with two twin beds each), a lovely kitchen, full bathroom and screened porch. On the second level you'll find the master bedroom with a private full bathroom, movie/game/yoga room, and a 2nd fully screened porch.

4.96 out of 5 average rating, 448 reviews

Townhouse in Ocean City

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

4.99 out of 5 average rating, 201 reviews

Guest suite in Berlin

Berlin/Ocean City Suite- Relax/Refresh near beach!

A remodeled, above garage guest suite separate from the main house in America's Coolest Small Town, Berlin,Md! You will benefit from a separate entrance to your above garage suite which will allow you to enjoy your own quiet space to relax and embrace the small, quaint town of Berlin, all while a mere 15 minutes to the beaches of OCEAN CITY and Assateague! Multiple dining experiences and tons of shopping await you in either historic Berlin or world famous Ocean City!

Superhost

Houseboat in Snow Hill

4.87 out of 5 average rating, 127 reviews

"Jolly"- Houseboat Getaway

#BoatLife! Jolly is a 42ft Holiday Mansion. Baywater Landing offers a laid back, coastal style. It buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & 3 outside deck areas to enjoy! Just 35 minutes from Ocean City, Assateague Island, and Chincoteague Island, this is the epicenter of everything coastal! A firepit in the sand just outside your door round out everything you'll need for a stress-free vacation.

Superhost

4.8 out of 5 average rating, 110 reviews

Mosaic Life Escapes -Bayfront Million Dollar Views

At Mosaic Life Escapes the BAYFRONT is our back yard! Safe gated community home. Water access for paddle boards & kayaks. Community fishing/crabbing pier 2 pools 3 ponds arcade room, playgrounds, paddle boats. 2 bd home w/a million dollar view. Minutes from Ocean City, Assateague Island & Casino. WiFi + 3 smart TVs We have implemented additional sanitizing procedures between guest stays to ensure a clean house! Perfect for a family or romantic get away!

4.99 out of 5 average rating, 227 reviews

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. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Apartment in Chincoteague

4.86 out of 5 average rating, 189 reviews

Sunset Haven Downtown

Broadband WIFI newly installed and dependable! This special place is located in the heart of historic downtown Chincoteague above a wine shop/jewelry boutique. Your backyard is a waterfront park with our famous Love Chairs! Watch the sunset from your waterfront window or deck. Walk to shopping, restaurants, and more! An apartment with old time charm and new polished adds to feel as modern as needed! Onsite Laundry- Linens provided

Guest suite in Chincoteague

4.98 out of 5 average rating, 287 reviews

Baywatch Upper-Waterfront & Roaming Ponies!

Discounted rates for weekly rentals Summer ‘25. Beautiful space in and out! Situated right on the bay with views of Assateague across the way, Chincoteague ponies are on premises. Coastal charm at its finest, there are 2 queen bedrooms and livingroom/breakfast room, all with a view. No full kitchen. Microwave, toaster, small fridge, stocked Keurig coffee and tea station and shared outdoor cooking area, sink and bbq grill.

Superhost

Tiny home in Salisbury

4.84 out of 5 average rating, 134 reviews

Cattail's Branch

Enjoy the lovely setting of this romantic spot in nature. Tiny house sits on Widow Hawkins Branch Creek and backs up to Johnson Wildlife Mtg Area. Great for bird watchers and nature lovers. Enjoy sitting by the fire pit or relaxing on spacious deck overlooking creek. Quiet and peaceful. Fully equipped kitchen, Queen bed, bathroom, pull out queen sofa bed with privacy wall to make 2rd bedroom. Close to beaches and town.

4.98 out of 5 average rating, 281 reviews

Tiny home in Selbyville

Destination Location! Farm Animals, Tours, Beaches

✨Scratch tiny house living off your bucket list!✨ Wake up to the cheerful sounds of barnyard animals that surround this unique tiny house escape! The "Garden Hideaway" is thoughtfully curated to inspire joy and help you reconnect with the simpler things in life. Just a few minutes from the beach, this tiny home comfortably sleeps two (2) guests, with an option to add a third (3) for a small fee.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Assateague Island vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Assateague Island

4.93 out of 5 average rating, 27 reviews

Cabin in Chincoteague

Nor’easter - water view - recent renovation

PinarRating, 5 stars2 weeks ago

This spot was such a wonderful little haven in Chincoteague. The cabin is spotless and the beds are so comfortable. The porch out front is the perfect spot to relax with coffee and a book. It's a very close drive to all the hotspots, but just out of the way enough to be truly peaceful. I would absolutely stay here again! Jess was a great host and super communicative as well!

4.96 out of 5 average rating, 73 reviews

Private pool, waterfront, kayaks, bikes, firepits!

LenoreRating, 5 stars1 month ago

We can't wait to return to Golden Quarter Farm! Charming and expansive, the property has everything we were looking for in a place to spend a relaxing weekend with extended family. The historic house is bright and roomy with a well-appointed kitchen; the bedrooms are unique, comfortable, and private; and the living space homey and inviting -- perfect for spending time together. The beautiful views of the riverfront drew everyone outside for walks down the pier, through the fields, and down the sun-dappled forest trails. It was a bit too chilly during our April stay, but the possibilities for enjoying the river (canoe, kayay, SUP) and lovely pool were nonetheless enticing. Finally, I must mention that Evie and Mary were extraordinarily welcoming and accomodating, from communicating proactively to preparing the home for our stay and checking in to make sure everything was perfect. Highly recommend!

5 out of 5 average rating, 23 reviews

The Cottage Bluefish -new in '24

CarolineRating, 5 stars1 day ago

We loved our stay at The Bluefish! The home was beautifully renovated, extremely clean and felt so welcoming. The location was ideal—just a quick walk to Main Street and the Island Creamery (a non-negotiable stop!). Jennifer was an exceptional host, always quick to respond and so helpful throughout our stay.

4.92 out of 5 average rating, 51 reviews

SpaciousCondo nearOcean City|Winery|Golf on 5Acres

PatrickRating, 5 stars6 days ago

This was a great place to get away for some peace and quiet. We had a lacrosse tournament in Berlin and the field was 15 minutes away. Beautiful home and very cozy. Very easy check in and Brenda was very quick to answer any question. Totally worth it!

4.86 out of 5 average rating, 21 reviews

Assateague - Direct Bayfront

SarahRating, 5 stars9 months ago

My family and I had a wonderful stay at Bobs!! We will be back! Quiet and peaceful but close to all the attractions too, just a short 20 min drive to OCMD. Perfect for families and huge yard for kids to play. Washer & dryer a huge plus! The sunrise is amazing from the dock, just a short walk and you’re there. Our favorite was the moon over the water at night, absolutely stunning. We hope to go back next year! Best place we have stayed in a long time!

4.98 out of 5 average rating, 63 reviews

Central Location- Walk to Dining & Entertainment!

KaraRating, 5 starstoday

I highly recommend this place!! The house was newly remodeled, very clean, had nice decor and furnishings and most of all felt like home. The hosts were wonderful to deal with and very accommodating!! Thanks for a wonderful place to stay during our family vacation ❤️

4.98 out of 5 average rating, 48 reviews

cozy sunset cottage

ElizabethRating, 5 stars1 month ago

Christy's Cottage was very comfortable and pet friendly. It was close to everything we wanted to do, and the kitchen was fully stocked. You can tell why she is considered a Superhost. We enjoyed our stay there, and would certainly consider returning. If you are going to see the ponies, we recommend Captain Mike with Up The Bay Pony Tours. Chincoteague and Assateague are lovely places to visit. Bring your camera if you are a nature lover. Pets aren't allowed on Assateague Island (not even in your car), but at Christy's we were able to leave our pups in their crates for a little while so that we go.