Holiday rentals in Assateague Island

4.94 out of 5 average rating, 109 reviews

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, 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.

4.92 out of 5 average rating, 148 reviews

Adorable Beach Cottage Just Steps From Town & Bay

New to AirBNB! Welcome to Wiggle Bay, a darling 1955 2 BR 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! --Stroll to local bookshop, coffee house, theatre, or Chincoteague Waterfront Park to feed the ducks--all just steps from your front door! -Situated on a quiet residential street -Just 4 blocks to Maddox Blvd (where all the action is) -2.3 mi to Assateague Seashore/Chincoteague Refuge

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.

4.96 out of 5 average rating, 449 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 :)

4.79 out of 5 average rating, 194 reviews

Home in Berlin

OC MD trip bayside, great amenities

Welcome to MERMAID DREAMS where you can have FUN or just RELAX! We are ONLY 5 miles from OC/beaches & Assateague National Park/beaches. Our gated, beautiful community, is bayside, has 2 awesome pools, big splash pool, rec center, a fishing/crabbing pier, pond with paddle boats, 2 playgrounds+ more For kiddos of all ages, we are located right next door to Frontier Town, which has awesome water slides , western shows, mini golf, a rope course, ice cream shop.. short term stay

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.

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.

4.86 out of 5 average rating, 189 reviews

Flat in Chincoteague

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.

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.

4.98 out of 5 average rating, 172 reviews

Cottage in Berlin

Bayfront Cottage w/ Amazing Views

Whether you’re enjoying time by the firepit or sipping coffee on the couch, the views of Sinepuxent Bay and Assateague Island make this cottage the ideal spot for your next vacation. The cottage is located in a quiet neighborhood and is only a short drive from Assateague Island, the historic town of Berlin, and the Ocean City Boardwalk.

Holiday rentals for every style

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Popular amenities for Assateague Island holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Assateague Island

4.93 out of 5 average rating, 28 reviews

Cabin in Chincoteague

Nor’easter - water view - recent renovation

JoelleRating, 5 stars2 weeks ago

Jess' place was perfect for our stay. With easy access to beach and to all the main attractions. We cooked several meals in the kitchen it was well stocked.

4.98 out of 5 average rating, 61 reviews

Guest house in Berlin

Resilience of Berlin, Charming 2 Bedroom Cottage.

LilyRating, 5 stars2 weeks ago

We loved our stay at Annie’s cottage. It was walkable to the cute and quaint town center where we consumed a year’s worth of ice cream in a few days. It’s was also only a 15-20 mins drive to ocean city beach or assateague island. We were pleasantly surprised when we checked in to the cottage. It was bigger in person and you can feel the love Annie has for the cottage through her decoration. We would highly recommend this place.

4.96 out of 5 average rating, 74 reviews

Home in Berlin

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!

4.9 out of 5 average rating, 49 reviews

Oysterhaven Cottage

RachelRating, 5 stars3 weeks ago

Convenient stay! We enjoyed the balcony and screened in porch with view of the water. Walkable to food on Main Street and quick drive to the park.

5 out of 5 average rating, 24 reviews

The Cottage Bluefish -new in '24

CarolineRating, 5 stars3 days 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.

4.95 out of 5 average rating, 19 reviews

Jay's Retreat

SteveRating, 5 stars6 days ago

Words just can’t describe how great of a time we had at Jays Retreat. Everything was labeled and easy to find. First rental that had everything you need and I mean everything. The views, crabbing at the dock, kayaking the canal at sunset, eating on the screened in porch, and so much more made this trip probably one of the best we ever taken to the island. Slept 4 adults, 2 kids and 2 dogs comfortably. Mosquitoes were a nuisance but thats any where on the island. We rode electric scooters into the town which was maybe a 10 minute ride. Water was hot, AC was on point. Kevin was very responsive and even provided an early check in. Appreciate everything about this trip!! Just sad it had to end! Can’t wait until next time.

4.98 out of 5 average rating, 63 reviews

Central Location- Walk to Dining & Entertainment!

KaraRating, 5 stars2 days ago

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 ❤️