Cottage vacation rentals in Assateague Island

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Top-rated cottage rentals in Assateague Island

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Top guest favorite

Cottage in Chincoteague

4.93 out of 5 average rating, 167 reviews

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!🐴🦪🌅

Top guest favorite

Cottage in Onancock

4.95 out of 5 average rating, 235 reviews

Eastern Shore Romantic Waterfront Getaway Upscale

A waterfront getaway at the newly renovated Westview Cottage on Onancock Creek just off the Chesapeake Bay. Wake up to beautiful water views through floor-to-ceiling glass doors. A private, peaceful escape in the country conveniently surrounded by fields and wildlife complete with a dock for crabbing and fishing (seasonal) 4 MI to Downtown Onancock & Restaurants 4.5 MI to Walmart 25 Mi to Camp Silver Beach 35 MI to Chincoteague Island 39 MI to Cape Charles >save listing to your wishlist<<

Top guest favorite

Cottage in Greenbush

4.98 out of 5 average rating, 124 reviews

Bell Farm Cottage LLC - quiet and peaceful

Cozy cottage located on a quiet backroad overlooking a wide open field & back deck provides warm & sunny space for relaxing or reading a book. The kitchen is fully equipped. BFC has a warm farm house feel w/ a touch of the beach. The bathroom has been updated to a more modern feel. Located only a few miles from both seaside and bayside boat ramps. A 7 minute drive to Onancock, Walmart, YMCA, shopping & many local shops for just the right souvenir. Wallops & Chincoteague are just a short drive.

Guest favorite

Cottage in Cambridge

4.97 out of 5 average rating, 141 reviews

Church Creek - waterfront cottage & pool - private

Close to Blackwater NWR and the Harriet Tubman Center, enjoy peaceful days at our secluded waterfront cottage on Church Creek. Great for winter remote work! Our closest neighbor is across a cove. Our estate offers 50 acres of privacy and one of the best waterfront views on the Chesapeake. Enjoy a view from every window and nature all around you. Excellent walking, swimming (in-ground pool-May 3-Oct 1), great birding and bicycling. Launch your kayak from the backyard. Perfect private getaway!

Guest favorite

Cottage in Hacksneck

4.94 out of 5 average rating, 115 reviews

Pretty Byrd Cottage, a Victorian Bayfront Getaway!

Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

Guest favorite

Cottage in Ocean View

4.91 out of 5 average rating, 234 reviews

Basil Cottage at Good Earth, near Bethany Beach

Welcome to the "Basil Cottage" at Good Earth. The cottage is the perfect size for a family, with 2 bedrooms (1 queen bed, and 2 single beds) a kitchen, and a living area. You'll be staying on our 10-acre property, 4.7 miles from Bethany Beach. Convenient amenities include an on-site restaurant, market, theater, and ample parking. Our AIRBNB "Village" includes 2 tiny houses, a lofted apartment, two cottages, a "glamper", and 4 tent sites. Staying at Good Earth is more than just a beach trip.

Top guest favorite

Cottage in Frankford

4.99 out of 5 average rating, 150 reviews

19th Century Coastal Cottage with Modern Amenities

Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. Exposed wood beams and interior brick walls as well as all the luxuries required for a rural escape. This charming cottage near the beach & is surrounded by enchanted gardens. You will swoon over the carved marble bathtub and gorgeous living areas. Perfect for a romantic getaway, Hobbs and Rose Cottage is waiting to create a memorable experience for you! NEW for 2025, our mediation room!

Guest favorite

Cottage in Reedville

4.95 out of 5 average rating, 133 reviews

Bull Neck Cottage

The cottage is located near "downtown" Reedville and provides a clean, comfortable and economical getaway. Come and enjoy water related activities and beautiful sights of Virginia's Northern Neck and the Chesapeake Bay. Tour the Watermen's Museum; cruise across the Chesapeake Bay to Tangier Island; walk, bike or kayak around Reedville, take a fishing charter or launch your boat nearby; enjoy great waterfront seafood restaurants; or just relax with a book.

Guest favorite

Cottage in Sussex County

4.97 out of 5 average rating, 119 reviews

Private Cottage * 1 bedroom+loft * Rehoboth Beach

Welcome to Salt Box Cottage! I am thrilled to share my dream vacation home with you! You will be a short distance away from all that Rehoboth, Dewey and Lowes Beaches have to offer. You will have access to 2 bicycles and beach chairs during your stay. When you are not out and about you will have access to the entire cottage, which is well appointed with a full kitchen, towels, linens, laundry room across the way and 2 free parking spots.

Top guest favorite

Cottage in Onancock

4.96 out of 5 average rating, 110 reviews

Little Cottage on the Creek

Experience Onancock....."a little slice of nowhere else". Whether you are looking for a romantic getaway for two, or just some rest and relaxation off the beaten path, Little Cottage on the Creek is the perfect place for your stay. Beautifully furnished and freshly renovated, this cozy waterfront cottage has all the comforts of home. Enjoy magnificent views of Onancock Creek along with the serenity for which the Eastern Shore is famous.

Guest favorite

Cottage in Berlin

4.98 out of 5 average rating, 166 reviews

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.

Top guest favorite

Cottage in Chincoteague

4.88 out of 5 average rating, 180 reviews

Sunshine Retreat

Cute and cozy two bedroom cottage on the famous island of Chincoteague. Colorful, relaxing getaway for up to four people. Two porches and great place to have that morning coffee. Outdoor shower - HOT and COLD water. NON-SMOKING (please smoke outside near parking area if necessary). NO PETS

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What guests are saying

'Cottage by the bay', sleeps 8 near Rehoboth beach

4.85 out of 5 average rating, 112 reviews6 months ago

Wonderful little A frame beach cabin feel. Timothy is very helpful and responsive. We did the dogfish dash and was the perfect little place to stay the night before our run. There is only 1 bathroom which wasn’t ideal in the morning for 4 people, but everything else is amazing!! Highly recommend :)

Cottage in Lewes

What guests are saying

Sea Glass Cottage - The best relaxation vacation.

5 out of 5 average rating, 44 reviews1 month ago

Sea Glass Cottage was a delight! The house was very clean, bright and totally charming! Doris has everything you could need for a couple nights or extended stay. I would suggest everyone who stays read her "Welcome" book. She has great suggestions for dining, sightseeing, art galleries, etc. Beds are comfortable and the bathroom is VERY large. Onancock is a fun, charming town to visit. We will definitely return and, if Doris will have us, we'll be staying at Sea Glass Cottage. Thanks Doris for a great visit! Cheryl and Jerry

Cottage in Onancock

What guests are saying

A-mazing Beach Cottage on Canal & Trolley Route

4.83 out of 5 average rating, 246 reviews1 month ago

We flew in for a funeral and Elisha was caring and understanding of our late arrival. The only suggestion I would like to see as an option is sheets on the beds and 1 towel per person minimum already on premise - There was a topper upstairs that helped give support on the twin mattress downstairs, which helped our daughter sleep. Other then that, the space was clean, organized, and the beds were comfy, spring/coil which we needed. It was a quiet neighborhood, close to the canal, tennis courts, church, and main road

Cottage in Bethany Beach

What guests are saying

5 Miles to Beach Quiet Secluded 3 Bedroom Cottage

5 out of 5 average rating, 4 reviews19 months ago

What a great house and location for our beach trip! The little boys played in the sand mound before and after each beach day! The outdoor shower is amazing, not rough and ugly like some. The back porch is a perfect place to land! We had everything we needed in the kitchen to have nice family dinners and relax at home in the evening. We had a blessed beach vacation at The Little Beach Cottage!

Cottage in Frankford

What guests are saying

Shady Shore Cottage in North Dewey Beach

4.9 out of 5 average rating, 101 reviews7 months ago

This place was a great stay for a small family that likes to walk everywhere on vacation! It was a short stroll to the beach for the kids. The place was just big enough for us for a long weekend. The kitchen and living area are very cute. It's also open enough that everyone can still be together while relaxing. The outside area is very private and has plenty of room for outdoor dining or activities should you want that. In some reviews, the traffic from 1 was noted. The noise or traffic wasn't even a thought for us! We definitely recommend future stays for others and will be back!

Cottage in Dewey Beach

What guests are saying

Cottage on Cabin Creek

4.95 out of 5 average rating, 61 reviews2 months ago

My husband and I traveled here for a night away from our children and work responsibilities. We were looking for some place that was private and on the water. This place was both and it did not disappoint! The loft was cozy and spacious and we loved looking out the windows at the water and rain. It was very clean and there were plenty of towels and blankets and other special touches. Janelle communicated with us ahead of time to make sure she was ready for our arrival and she was kind and responsive throughout the process. We also found it easy to get into Easton for dinner at The Stewart, which was a treat, and then return back to the cabin. I would stay here again in a heartbeat -- but hopefully for longer next time.

Cottage in East New Market

What guests are saying

Holiday Cottages-Nautical Cottage

4.75 out of 5 average rating, 16 reviews1 week ago

Flawless from start to finish. I've stayed in dozens of high-end hotels across the country, and this little cottage was THE cleanest space I've ever had the pleasure of staying in. Everything glistened like it was new. My family and I felt very much at home from the time we entered to the time we left. Top notch! Many thanks for a job well done and facilities that didn't disappoint.

Cottage in Chincoteague