Vacation rentals in Toms Cove

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, 149 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

4.99 out of 5 average rating, 265 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!

A cozy rec room is showcased with a vaulted wood-paneled ceiling. Two comfortable chairs are positioned in front of a large projector screen, creating an ideal viewing area. Soft lighting adds warmth, while a few shelves with storage bins and a small table enhance the space's functionality.

4.97 out of 5 average rating, 166 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, 160 reviews

Cottage in Chincoteague

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, 449 reviews

An overhead view of the open living area reveals a cozy couch and a circular chair, complemented by a modern coffee table. Sliding glass doors offer unobstructed bay views, leading to a porch with outdoor seating. Natural light fills the room, creating a bright and airy feel.

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 :)

4.97 out of 5 average rating, 116 reviews

Home in Cape Charles

Wander Cape Charles

A sanctuary, an oasis, a one of a kind experience communing with nature while lounging in civilized splendor—all are apt descriptions of this New York architect designed beach house on the shores of the Chesapeake Bay. Guests enjoy stunning waterfront views from a finished floor height of 36 feet. The Eastern Shore of Virginia is famous for its flat tidewaters, but this property is perched amongst unusual relic Sandhills, complete with pines, gum trees and vast sea and sunset vistas.

4.96 out of 5 average rating, 275 reviews

A wide-angle view captures the beach and ocean, with soft waves lapping at the shore. The surrounding buildings are visible, including the condominium structure featuring floor-to-ceiling windows. A beachfront pool and tennis courts occupy the area below, while sunbathers and umbrellas dot the sandy beach.

Condo in Ocean City

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

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, 131 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.

4.75 out of 5 average rating, 211 reviews

The image displays a serene sunset over a body of water, with the sun positioned low on the horizon. Silhouettes of trees and vegetation can be seen along the far shore, contrasting against the warm hues of orange and pink in the evening sky.

Guest suite in Crisfield

The Serenity House

Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.

4.92 out of 5 average rating, 230 reviews

A spacious living area showcases a modern kitchen with sleek cabinetry and a cozy seating arrangement. Large glass doors provide a view of the ocean and lead to a private balcony. Decorative elements include a patterned rug and two vibrant blue chairs.

Condo in Ocean City

Sun, Sand & Sea | Your Cozy Oceanfront Hideaway

**2025 guests: Our pool and hot tub are in the process of being renovated and will be closed during your stay. This does not impact our condo, but you will not be able to use these amenities.** -Oceanfront -Indoor pool & Hot tub -Walk to local dining and shopping -Elevator accessible plus luggage carts -Full kitchen for cooking meals -Fast Wifi and Streaming TVs -Fully Stocked Home: Clean linens, towels, toilet paper, paper towels & more!

Guest suite in Chincoteague

A serene outdoor view is captured from the balcony, revealing a sandy beach and calm waters beyond. A partially covered deck area is visible, alongside a barbecue grill. Lush trees frame the scene, providing a natural backdrop to the tranquil setting.

4.94 out of 5 average rating, 316 reviews

Baywatch North-Waterfront & Roaming Ponies

Lovely space! 2 queen bdrm 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, shared patio cooking area, bbq grill, fantastic view, beach items, plenty of parking, 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 too!

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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.

4.72 out of 5 average rating, 100 reviews

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.

Cottage in Chincoteague

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.

A coffee maker is positioned on a marble countertop, accompanied by a sign that reads 'HELLO COFFEE.' On the left, a wall-mounted holder displays coffee pods, while to the right, two wooden containers filled with coffee supplies are visible.

4.99 out of 5 average rating, 71 reviews

Bikes-Kayaks-Outdoor Shower Grill-Firepit-Beach Eq

LorraineRating, 5 stars1 week ago

This place had a great location; it was less than 10 minutes for the local restaurants and only a 15 drive to the beach. The kitchen had everything you needed, there was plenty of space for atleast 6 people (even though there was just the two of us). The airbnb itself was really charming. Host was amazing, really responsive and communicative. Their checkin and checkout procedures were really clear. My only “asterisk” is that since it is an older house and in the middle of a marshland basically, it was pretty humid inside. It seems normal for the area especially considering it was raining half of our stay. The AC boxes in every room definitely helped but just something to note about our stay. I’d recommend a dehumidifier to the hosts. Overall a great stay, would recommend this place to all when staying in Chincoteague!!

An indoor garage game room is showcased, featuring a blue ping pong table positioned centrally. Exposed wooden beams and insulation panels line the walls. A staircase is present in the corner leading to an upper level, while a white chair is placed near a window.

5 out of 5 average rating, 15 reviews

‘Beach Bay Pony Place’ w/ Ponies: 1 Mi to Water!

DanelRating, 5 stars4 weeks ago

Our stay was very peaceful, had 4 beautiful ponies behind a very well maintained home. Enjoy walking around town and the many sea food restaurants. Enjoy the park looking for the somewhat wild ponies, hiking, biking, and the beach was all worth the trip! Was fun and very relaxing trip for us!

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!!!

4.98 out of 5 average rating, 64 reviews

Central Location- Walk to Dining & Entertainment!

JackieRating, 5 stars2 days ago

We had a great time at the Reel Deal on Teal. The place was adorable, beautifully decorated, and cozy. He provided everything, and I mean everything you could possibly need. Kitchen is expertly stocked and allowed us to cook a few meals. The location was right in the middle of everything. Chip was an excellent host and had great recommendations for restaurants and things to do. He even provided a park pass to see the ponies, which was much appreciated. We would highly recommend this place to anyone looking for a relaxing getaway.

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!