Vacation rentals in Toms Cove

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.

A comfortable living area is showcased, featuring large windows that provide natural light. A circular coffee table sits at the center, surrounded by a light sofa and armchair. A television is mounted on the wall, while a decorative bench adds a cozy touch.

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.

A welcoming front porch is presented with two vibrant purple Adirondack chairs and a matching table. A door with six glass panels, painted in the same shade of purple, serves as the entry point. Bright sunlight highlights the charming outdoor space.

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!

Two hanging chairs, adorned with floral pillows, are suspended in a screened porch. A small wooden table stands between the chairs, featuring a candle and decorative items. Soft lighting enhances the relaxed ambiance of the space, creating a cozy retreat.

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

A charming two-story house with a welcoming front porch is surrounded by lush greenery. The exterior features a classic architectural design with multiple gabled roofs and symmetrical windows. A circular garden bed, centered in a gravel area, adds a touch of color to the inviting landscape.

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

A charming outdoor area is showcased along a wooden walkway beside the water. Colorful banners and umbrellas adorn the pavilion, while wooden chairs invite relaxation. The grassy space features tiki torches, and boats can be seen docked in the distance under a bright blue sky.

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.

Apartment in Chincoteague

The bathroom is designed with neutral tones, showcasing a glass-enclosed shower with textured tiles. A modern toilet is positioned nearby, and a small wastebasket is placed next to a striped rug on the floor. Shelves house toiletries for convenience.

4.86 out of 5 average rating, 189 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

Guest suite in Chincoteague

A charming white house with a sloped roof is set amidst well-kept greenery. A smooth, gravel pathway leads to the entrance, flanked by clusters of white flowers. In the background, trees provide a natural border, with open views toward the bay and the horizon.

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.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Toms Cove vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Toms Cove

4.93 out of 5 average rating, 28 reviews

The entrance of the home is illuminated by string lights, creating a warm ambiance. A covered porch features a seating area with a table and chairs, while decorative lanterns are positioned near the steps. The home's exterior is characterized by a light grey finish.

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.

A thatched-roof gazebo is positioned on a sandy shore, overlooking calm waters during sunset. The sky transitions into a gradient of warm colors, reflecting on the water's surface. Wooden posts line the shore, adding to the serene waterfront scene.

4.72 out of 5 average rating, 99 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.

4.93 out of 5 average rating, 58 reviews

A wooden pier extends towards a rustic boathouse, reflecting warm hues from the sunset. Tall grasses frame the walkway, while the shimmering water surrounds the structure. Soft light glows from the windows, creating an inviting atmosphere amid the serene landscape.

Cabin in Chincoteague

The Boathouse: Charming & Historic Waterfront Stay

ThomasRating, 5 stars2 weeks ago

The Boathouse is such a wonderful place to stay. It is so unique and has an abundance of charm. The beautiful setting overlooking the marsh from inside and on the deck is incredible! We had a fantastic time at this lovely place and the beautiful surrounding area as well. Christian and Ashling were fantastic hosts with timely and responsive communication and great recommendations for you to do during your stay. We highly recommend the Boathouse!!!

4.96 out of 5 average rating, 73 reviews

A well-organized kitchen cabinet displays various spice jars arranged on metal racks. Clear containers are visible alongside jars of oil and sugar. A tiered shelf provides additional space for storage, contributing to efficient kitchen organization.

Condo 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!

Guesthouse in Chincoteague

A kitchen area features a countertop with two black stools, equipped with soft cushions. A stainless steel refrigerator is visible, and essential appliances like a sink, a hot plate, and a microwave are neatly arranged. Wooden paneling gives the space a warm feel.

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!

A screened-in outdoor lounge area shows comfortable grey seating paired with a round dining table. The natural light filters through bamboo shades, and a patterned area rug enhances the space. A backdrop of greenery is visible through the screens, providing a serene environment.

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!