House holiday rentals in Chincoteague Bay

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Top-rated house rentals in Chincoteague Bay

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

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Guest favourite
A charming tiny house features wooden shingles and a welcoming front door. It is framed by colorful flowers in a garden, enhancing the outdoor landscape. A sign above the door adds a personal touch, while large windows allow natural light to fill the space.
Home in Ocean View
4.91 out of 5 average rating, 605 reviews

Tiny House at Good Earth, near Bethany Beach

A custom 165 sq. ft. "Tiny House" located right between our theater and the garden dining area. True to the show "Tiny House Nation".. cool interior with custom woodwork, stairs to a lofted bed. Fully functioning kitchen. Spacious bathroom & shower. We provide TV and internet in the unit. We have 2 on-site restuarants, market, theater, and parking. Our AIRBNB village consists of 2 tiny houses, 2 cottages, tent sites, a loft appartment, and more! Staying at Good Earth is more than a beach trip!

Guest favourite
Home in Chincoteague
4.94 out of 5 average rating, 126 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, kayaking on the 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.

Top guest favourite
The exterior of the cottage is framed by vibrant flowerbeds filled with blooming roses and lush green shrubs. A well-manicured path leads to the entrance, flanked by tall greenery, with glimpses of the sparkling water visible in the background.
Home in Shady Side
5 out of 5 average rating, 185 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5-star retreat for those who value tranquility over spectacle. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our reviews.

Top guest favourite
A bright living area features large glass doors that open to an oceanfront deck, enhancing the panoramic views. Soft, light-colored furnishings are arranged around a natural wood coffee table, with textured area rugs underfoot. A telescope is positioned by the window for viewing the coastline.
Home in Strathmere
5 out of 5 average rating, 105 reviews

Strathmere Beachfront House

Luxury Beachfront Home Welcome to the Strathmere Beachfront home. A beautifully designed, luxury vacation home, where every detail is set to provide a you dream getaway. When you enter the home, you will be immediately taken by the panoramic ocean views from Atlantic City to Avalon. This well-appointed home, from chef’s kitchen Wolf and Sub-Zero appliances, to the Serena and Lily bedding, to the coastal / modern furniture, provides you and your family a welcoming environment. Treat yourself!

Top guest favourite
The historic home features a charming exterior with a mix of white clapboard and dark shingles. An inviting porch is framed by green shutters and surrounded by well-maintained landscaping. A gravel driveway leads to the front entrance, enhancing the property’s welcoming appeal.
Home in Lusby
5 out of 5 average rating, 156 reviews

Historic Rousby Hall, Waterfront, Pool, Beach

**Heated pool open to Nov 2. Thanksgiving chef dinner options** Rousby Hall is a stunning 5-star waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee additional).

Top guest favourite
A spacious outdoor dining area features a long table set with colorful placemats and floral centerpieces. The view overlooks the water and a tree, with a pier visible in the distance under a clear blue sky.
Home in Gloucester Courthouse
4.97 out of 5 average rating, 321 reviews

"Bee-Z Haven" Waterfront Cottage on the Ware River

Curious about what makes Gloucester so wonderful? Live like a local at this Upscale Waterfront Retreat and find out for yourself why renters say "Enjoy the Breath Taking Views". Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our area is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

Guest favourite
A charming two-story island home is nestled among tall trees, providing a natural setting. The structure features a sloped roof and a front porch with a railing. Sunlight filters through the branches, casting dappled shadows on the ground.
Home in Chincoteague
4.97 out of 5 average rating, 179 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.

Top guest favourite
A bright sun porch features a round glass dining table surrounded by four light-colored chairs. Large windows provide views of the waterfront, allowing natural light to fill the space. A cozy seating area is visible in the background, offering a serene atmosphere.
Home in Leonardtown
5 out of 5 average rating, 135 reviews

White Point Cottage -- Quiet Waterfront Getaway

Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. More on IG @whitepointcottage, and be sure to visit our sister property, Water's Edge Cottage.

Guest favourite
A serene canal view captures waterfront homes reflecting in calm waters at sunset. Docked boats and lush trees frame the scene, showcasing the tranquil atmosphere of the eastern shore. The clear sky hints at the day's end, lending a peaceful ambiance to the surroundings.
Home in Greenbackville
4.91 out of 5 average rating, 100 reviews

Stunning waterfront panoramic view getaway house

Welcome to this thoughtfully remodeled waterfront property on the beautiful eastern shore of Virginia. Immerse yourself in jaw-dropping panoramic canal views of the Chincoteague Bay. Secluded escape for the nature enthusiast, balanced with country club amenities. Pools, boating and a golf course are within walking distance. Outdoor adventures and pristine beaches are just a short drive away! This property was designed to gather, recharge, explore, love, work remotely and inspire.

Guest favourite
Two classic white Adirondack chairs are positioned on a grassy bank overlooking the calm water of the Rappahannock River, framed by gently swaying trees. The sky displays a soft transition of colors as the sun sets, creating a serene and inviting view.
Home in Locust Hill
4.97 out of 5 average rating, 150 reviews

Waterfront Cottage Getaway Views/Kayaks/Fire Pit

A timeless cottage on a quiet property on the Rappahannock River with charming rose garden, relaxing pool, and quintessentially Virginia feel. Find us on IG @rosehilllcottagerappahannock! Explore nearby towns of Urbanna, White Stone, and Irvington, or stay close to home to enjoy sweeping views, waterfront adirondack chairs, and kayaks — perfect for a cocktail or coffee, or take a dip in the river or pool. With open living spaces and thoughtful decor, this is your waterfront retreat.

Top guest favourite
An aerial view captures the riverfront A-Frame home surrounded by lush greenery. The spacious deck extends toward the water, showcasing a blend of natural beauty and modern architecture under a soft, early evening sky.
Home in Charles City
4.99 out of 5 average rating, 308 reviews

Hutch's Bluff - Waterfront near Williamsburg

Charming riverfront A-Frame home on 2 acres overlooking the Chickahominy River. Completely updated interior, including all furnishings and appliances. Wake in a King bed loft space with a majestic view of the river, or choose one of the two Queen bedrooms below. First floor all tile bathroom with a walk in shower. Stainless appliances and granite countertops. Bring your fishing gear, relax at the end of the pier, or enjoy the views from the large deck and fire pit.

Guest favourite
A charming bungalow is shown at dusk, featuring large windows that allow natural light to fill the interior. A neatly landscaped yard complements the exterior, which is painted in soft blue tones. A parking sign is visible in the foreground, indicating designated parking availability.
Home in Chincoteague
4.95 out of 5 average rating, 132 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.

Popular amenities for house rentals in Chincoteague Bay