Holiday rentals in Assateague Island

4.93 out of 5 average rating, 107 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.

4.92 out of 5 average rating, 146 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

Superhost

Cottage in Chincoteague

4.83 out of 5 average rating, 99 reviews

"3 Sisters" Ivy's Cottage-Lovely downtown cottage

Just a few miles from the Chincoteague National Wildlife Refuge & Assateague Beach. Ivy's Cottage offers a great in-town location that's close to shops, restaurants, waterfront park, & public fishing pier. This beautifully renovated, this Chincoteague Island Cottage Features: Lovely eat in kitchen, fully equipped w/ all amenities. Cozy living room w/ full sleeper sofa & recliner. Queen bedroom w/ adjacent full bathroom. Large front porch perfect for outdoor dining & park style charcoal grill!

4.89 out of 5 average rating, 282 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, 446 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 :)

4.98 out of 5 average rating, 199 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, 126 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.

Guest suite in Ocean City

4.98 out of 5 average rating, 362 reviews

The Elbridge Bayfront Studio

The Elbridge is a luxury studio apartment in downtown Ocean City. Beautiful bay view from studio windows. This bayside studio includes parking, a private garden entrance, and luxurious king bed. Located 4 blocks from the beach, the space is in a downtown residential neighborhood. Additionally included are bikes, bodyboards, beach chairs and a beach umbrella. Walking distance to delicious local restaurants, the boardwalk, and the beach!

4.87 out of 5 average rating, 187 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, 280 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, 171 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

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Popular amenities for Assateague Island holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Assateague Island

4.98 out of 5 average rating, 61 reviews

Guest house in Berlin

Resilience of Berlin, Charming 2 Bedroom Cottage.

LilyRating, 5 stars1 week 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.

5 out of 5 average rating, 22 reviews

The Cottage Bluefish -new in '24

AnnaRating, 5 stars3 weeks ago

We've visited Chincoteague many times, but this was the closest we have ever stayed to town. We absolutely LOVED being able to walk to many of our favorite spots like Amarin and Island Creamery. We also enjoyed shopping at Saturday's farmer's market right down the street. The house was private and serene - a true chef's kiss. Dinner on the back deck was perfection. I told my husband so many times I wish we stayed longer, so take it from me - book that extra day! We will definitely be back.

4.92 out of 5 average rating, 13 reviews

Flat in Snow Hill

The Top of Downtown Snow Hill

HeatherRating, 5 stars1 week ago

Blair's condo was the perfect spot for our weekend trip. The condo was beautiful with all the necessities. It also has a good location, and is centrally located to Snow Hill shops and dining as well as a short drive from Assateague and Ocean City. We highly recommend this stay!

4.94 out of 5 average rating, 18 reviews

Jay's Retreat

KellyRating, 5 stars1 week ago

We absolutely loved this place. It was our first time in Chincoteague. Definitely will be returning and definitely would stay at Kevin’s again!

4.93 out of 5 average rating, 92 reviews

Cottage in Berlin

Quiet Retreat near Assateague Island

DeniseRating, 5 stars8 months ago

This was our second trip to Catherine's retreat and we loved our stay this time even more than our first. Both Catherine and her husband assisted us when we had questions and provided suggestions for local events. The property is such a restful delight; from the pool, the views of the marshes, the quiet, and the plethora of wildlife to see. The home is comfy and we had everything we needed to make ourselves great meals and just soothe the soul. Between spending time on Assateague by day and returning to this special place at night, we came home restored. Thanks again!

5 out of 5 average rating, 7 reviews

Cottage in Princess Anne

Waterfront Cottage in Mt. Vernon

ChristinaRating, 5 stars1 week ago

We had an amazing stay at Melanie’s waterfront home! The location was absolutely perfect right on the water with stunning views and peaceful surroundings. We loved having access to the kayaks, grill, and outdoor furniture it made it easy to relax and enjoy the beautiful setting. The house was fully equipped with everything we needed for a comfortable stay, and the neighborhood was quiet with super friendly neighbors. Melanie was a fantastic host thoughtful, responsive, and even left us a list of local restaurant recommendations, which turned out to be excellent! This spot was exactly what we were looking for, and we’re already looking forward to coming back. Highly recommend!

4.98 out of 5 average rating, 48 reviews

cozy sunset cottage

ElizabethRating, 5 stars3 weeks 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.