Holiday rentals in Toms Cove

4.93 out of 5 average rating, 171 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!🐴🦪🌅

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

4.81 out of 5 average rating, 146 reviews

Bungalow in Horntown

Nature's retreat @ the Bug-a-Boo. Beaches nearby

We're inside a lovely gated campground community with full amenities @ the Club House: Wi-Fi, pool, fishing n crabbing, boat ramp, laundry, and bath houses. The Bug-a-Boo is a lovely single dwelling home. It is ADA handicap accessible. There's an outdoor fire pit and space for camping. We are 20 miles from Chincoteague National Wildlife Refuge with miles of protected beaches. This is a peaceful place for soul searching & social distancing. We are also 42 mi from Assateague Is. Nat. Seashore.

4.83 out of 5 average rating, 100 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!

4.99 out of 5 average rating, 263 reviews

Farm stay in Onancock

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!

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.

4.95 out of 5 average rating, 159 reviews

Summer's Sea Shanty on Chincoteague Island

Summer's Sea Shanty is a delightful Chincoteague coastal cottage that’s perfect for couples, families, or small groups of friends. We've worked hard to make this the ideal modern day beach retreat. This home boasts screened in front and back porches, a fire pit, an open/functional floor plan. We're pet and kid friendly with luxury linens and rugs and dish ware... We're proud to be the best of the best on the island. We're centrally located and minutes from Assateague National Seashore.

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 :)

Tiny home in Cape Charles

4.98 out of 5 average rating, 317 reviews

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

4.87 out of 5 average rating, 127 reviews

Houseboat in Snow Hill

"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.

4.95 out of 5 average rating, 111 reviews

The Neigh-Neigh - Location! Location! Location!

Named in honor of the ponies that first put Chincoteague on the map, this charming newly renovated family getaway is walking/biking/and wheeling distance to shops, galleries, restaurants, waterfront park, library, beach, wild ponies, and movie theater. Come relax in a stunning, clean, 2 BR, 2 full BA plus oversized upstairs den with queen and twin beds and a futon bed that comfortably sleeps 8. The amenities and unique offers this place has, is not to be missed.

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

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Other great holiday rentals in Toms Cove

4.94 out of 5 average rating, 109 reviews

Dragonfli Bay House on Chincoteague Island

BillieRating, 5 stars2 weeks ago

The Dragonfli was everything you would hope for when you book an Airbnb. The home was beautiful, clean, and very accommodating! It is in a beautiful part of the island, and more of a quiet neighborhood. We definitely plan to come back!

4.72 out of 5 average rating, 100 reviews

SNUG HARBOR waterfront cottage with a grand view!

AlexandraRating, 5 stars2 weeks ago

We ABSOLUTELY loved our visit, and plan to return and stay with Basia! Our weekend consisted of rainy weather and she offered us a covered porch which was well worth it!! Each morning we had a peaceful water view with the horses in the distance. I don’t think it could get any better. The boat tour was SO much fun. Basia stayed in contact with us about when would be the better time to go. She really looked out for us when the weather would be at its peak. Her recommendations never failed to impress. Thank you SO much for having us!! We plan to be back.

4.96 out of 5 average rating, 73 reviews

Apartment in Ocean City

Gorgeous New Beachfront! King Bed, Direct Sea View

KaitlynRating, 5 stars1 week ago

What a wonderful experience! Josh and Kathy were in incredible hosts and their home was perfect for our family of 4. We couldn’t have asked for a better trip. Everything was so easy, and we felt so comfortable!

Guest house in Chincoteague

5 out of 5 average rating, 24 reviews

Pirate’s Hideaway

RachelRating, 5 stars1 week ago

Super clean place and a great walkable location to the main strip of shops and restaurants. Amy provided clear instructions and we loved the selection of board games to wind down after a fun filled day!

4.98 out of 5 average rating, 49 reviews

cozy sunset cottage

ZaneRating, 5 starstoday

the place was beautiful and felt very cozy! It was a very short drive to and from the beach as well with plenty of things to do nearby!

4.89 out of 5 average rating, 144 reviews

Pony Pines!Your Waterfront Getaway Cottage Awaits!

JenniferRating, 5 stars2 weeks ago

Eric’s place was wonderful for our family of four to stay for the weekend. The backyard especially stood out - great screened in porch and firepit to hang out!

4.94 out of 5 average rating, 90 reviews

Breeze on Inn

JimRating, 5 stars3 weeks ago

The house is spotless, clean and comfy. Host is friendly and responsive. The only bad thing was the clock in Livingroom always shows 6:21. But otherwise is perfect. I definitely will stay there again if I'm around the area.