Waterfront holiday rentals in Assateague Island

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Top-rated waterfront rentals in Assateague Island

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

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Guest favourite

Cottage

4.96 out of 5 average rating, 226 reviews

Eastern Shore Modern 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<<

Guest favourite

Apartment

4.97 out of 5 average rating, 148 reviews

Escape by the Bay

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

Guest favourite

Cottage

4.94 out of 5 average rating, 109 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 favourite

Farm stay

4.99 out of 5 average rating, 219 reviews

Private romantic pet friendly waterfront cottage

On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

Guest favourite

Home

4.97 out of 5 average rating, 200 reviews

Jay’s Retreat: EV Charger-Fire Pit-Kayaks-Bikes

Welcome to Jay's Retreat, your perfect escape just minutes from Assateague National Seashore and the iconic Chincoteague Ponies! This fully equipped 1,000 sq. ft. home features 3 cozy bedrooms, a fire pit for starry nights, kayaks, bikes, and a private dock for your water adventures. Enjoy swimming, fishing, hiking, and bird watching right at nature’s doorstep. With linens and towels included, plus an EV charger for your convenience, you’ll have everything you need for a memorable getaway.

Guest favourite

Townhouse

4.97 out of 5 average rating, 392 reviews

Edgewater Escape - Bayfront Condo w/Private Porch

Welcome to our "Edgewater Escape." These buildings were built in the 1960's and literally hang entirely over the bay in downtown in 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 king sized bed and the downstairs couch pulls out into a comfortable queen bed. Full size kitchen with microwave, fridge, electric range, and coffee maker. Located on 7th street, over the bay :)

Guest favourite

Guest suite

4.93 out of 5 average rating, 267 reviews

Baywatch North-Waterfront & Roaming Ponies

This is a lovely space! 2 queen bedroom unit decorated with coastal charm, each with a door to the outside. Make-shift kitchen with microwave, small fridge, stoked Keuring coffee and tea bar, patio cooking area shared with upstairs unit, bbq grill, fantastic view, beach items, plenty of parking, private lane, 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 on premises!

Guest favourite

Tiny home

4.93 out of 5 average rating, 471 reviews

Little Red House on a Farm - Quiet Rural Waterview

The Little Red House VA is a tiny house with big charm. This rural cottage on a 50 acre farm is nestled between peaceful fields, woods, marsh and creek. Curated with hygge comfort and efficiency in mind, you'll love the natural light and serene decor. • Epic stargazing • Heavenly private outdoor shower • Firepit with wood provided • Ample open spaces • Peace and quiet for sleeping • Comfy patio seating for chilling, coffee, and cocktails • Fast WIFI. • Proud Superhost for 10+ years!

Guest favourite

Cottage

4.99 out of 5 average rating, 206 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Winter time is a great time at Rumbley! Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all window. Look out to 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 Wifi, Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Guest favourite

Apartment

4.96 out of 5 average rating, 225 reviews

Caramar Couples Retreat

This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.

Guest favourite

Cottage

4.93 out of 5 average rating, 173 reviews

Heaven on the Bay - A Peaceful Waterfront Retreat

This Chesapeake Bayfront cottage has spectacular views to take you away from everything in any season. It boasts more than 120 feet of waterfront, and you can dangle your feet off the 70 ft “dock of the bay”. Launch kayaks from the small sandy beach in summer, or cozy up to the wood stove in the winter. Inside, you’ll find wood floors throughout, modern kitchen & baths with bay views from every room. Kayaks, SUP, bicycles & crab traps too!

Guest favourite

Rental unit

4.85 out of 5 average rating, 156 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