Vacation rentals in Bennett Harbor

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Bennett Harbor

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

%{current} / %{total}1 / 1

Top guest favorite

A well-appointed bedroom features a spacious bed with a textured white cover. Colorful accent pillows add depth to the decor. A wooden dresser stands against one wall, while a bedside lamp illuminates the space. Natural light filters through a window adorned with light curtains.

Home in Smithfield

4.97 out of 5 average rating, 305 reviews

Mason Manor - Downtown Smithfield next to WCP

Historic Smithfield 233 S Mason Street 2 Bedrooms 1 Bath Located in the heart of historic Smithfield boasts old world charm and character with a touch of today’s conveniences. The living room has gas fireplace for cool evenings & leads to dining area & updated fully equipped kitchen. The full bath is updated with jetted tub. Front porch swing for relaxing and back deck for entertainment. Windsor Castle Park just steps away. Located just around the corner from restaurants, shopping & more.

Top guest favorite

The Purple Room features a spacious bed with white linens and purple accents. A cozy seating area is visible beside large windows with light filtering through sheer curtains. Decorative elements, including wall art and a soft purple rug, enhance the vibrant atmosphere.

Guest suite in Chesapeake

4.96 out of 5 average rating, 365 reviews

Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!

Welcome to The Purple Room, get ready for an AirBnB experience unlike any others. This one of a kind AirBnB not only offers a memorable staying experience, but will be a welcome end to an exciting day at the beach, dinner and drinks at a local restaurant or bar, or an adventurous day exploring all the culture and history the area has to offer. We are centrally located, offer free parking, wifi and kitchenette. We have local art, free wine and food samples. Come see what the excitement is about!

Top guest favorite

A private balcony is outlined by wooden railings, featuring two white adirondack chairs. A potted plant with white flowers adds a touch of greenery, while a tranquil view of the water stretches out toward the horizon under a clear sky.

Guesthouse in Coinjock

4.98 out of 5 average rating, 401 reviews

Church's Island Carriage House

Welcome to Church's Island Carriage House, located on the Currituck Sound directly across from the Corolla Lighthouse. Watch the the sun rise over a panoramic view of the Currituck Sound from your private balcony as you enjoy your morning coffee. It's the perfect set up for a single or couple with separate bedroom, bath, living area and kitchenette. The apartment is up one fight of stairs. Private and located in the quaint community of Waterlily just 30 minutes from OBX and the Virginia line.

Guest favorite

Large windows provide stunning views of the lake, reflecting vibrant colors of the sunset. A small potted plant sits on a table beside a white chair, while light from the setting sun casts a warm glow across the interior space.

Home in Norfolk

4.97 out of 5 average rating, 122 reviews

THE POINT! Private waterfront Oasis!

Enjoy breath taking views & a fully equipped home w/ many amenities. Looking for a private & intimate experience of quality time & a relaxing retreat w/ nature & ample space to spread out, this is IT! Convenient to VB Oceanfront, Downtown Norfolk, Rivers Casino, Waterside & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect family/friends group trips, 12 minutes from Carnival Cruise Port. Oh & bring your fishing poles, river is fully stocked!

Guest favorite

A classic Cape Cod home is surrounded by well-maintained greenery. The brick exterior is complemented by a gravel pathway leading to the front steps. A concrete driveway provides access to an attached garage, while flags are displayed on the front porch, enhancing the home's welcoming appearance.

Home in Portsmouth

4.97 out of 5 average rating, 39 reviews

The Bartlett Inn

Welcome to The Bartlett Inn, a charming Cape Cod home built in 1948, nestled in the serene Green Acres neighborhood of Portsmouth, VA. Enjoy the timeless appeal of hardwood floors, traditional Cape Cod architecture, and the peaceful ambiance of a well-established yard and neighborhood. Conveniently located near parks, shopping, and dining options, casino, hospitals, bases and so much more! The Bartlett Inn offers a delightful blend of nostalgia and comfort that welcomes anyone home.

Top guest favorite

A house with a blue and white exterior is situated on the edge of the water, reflecting in the calm surface. Lily pads float nearby, while flags adorn the porch railing, indicating a welcoming environment. Greenery surrounds the area, enhancing the serene landscape.

Home in Moyock

4.94 out of 5 average rating, 383 reviews

Sportsman's Paradise ( Hunting & Fishing )

Sportsman's Paradise is just minutes away from the Currituck Sound which is famous for it's duck hunting and fishing. It overlooks Tull's Bay and Tull's Creek and is surrounded by the Northwest River Marsh Game Lands. The kitchen and living room have 9 windows so you can look out three sides of the house at the water. The walls are old rough cut boards and the ceilings are plywood. The living room and bedrooms are carpeted and the bathrooms and kitchen are laminate wood floor.

Guest favorite

A charming two-story cottage is set on a lush green lawn, with a clear view of the Chesapeake Bay in the background. The cottage features large windows and a sloped roof, with a small wooden addition on one side, surrounded by well-maintained grass.

Tiny home in Cape Charles

4.98 out of 5 average rating, 341 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.

Guest favorite

A two-story cabin made of wood stands beside a serene pond, surrounded by tall pine trees. The cabin features large windows and a spacious deck with rocking chairs, inviting peaceful moments by the water's edge.

Cabin in Cape Charles

4.95 out of 5 average rating, 219 reviews

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

Top guest favorite

A two-story house featuring a welcoming porch with white railings and steps leading to the front door. The exterior is clad in light siding, complemented by well-kept landscaping and a driveway leading to a garage on the right. Trees provide a natural backdrop.

Home in Suffolk

4.85 out of 5 average rating, 108 reviews

Perfect Getaway!

Home away from home!! Beautiful 2 story house with 3 bedrooms, 3 bathrooms, and a huge playroom over the garage. The master suite has a beautiful bathroom with a jacuzzi tub, and huge walk in shower. The fenced in backyard has plenty of space to run around, and has an awesome saltwater inground pool for fun! In addition, there is a 2 level, new deck, and patio furniture to sit and relax on. There is something for everyone to do here.. I’m positive you will love it!

Guest favorite

An inviting interior features a spacious bed adorned with soft bedding and decorative pillows. Natural light filters through large windows, illuminating the cozy sitting area with comfortable chairs and a wooden coffee table. Artwork and decorative accents add charm to the welcoming atmosphere.

Guesthouse in Suffolk

4.88 out of 5 average rating, 26 reviews

The Harlequin Cottage

This unique place has a style all its own. Cottages on the Point was launched in 2018 and offers timeless interior styling and stunning resort style outdoor views. The property features a seasonal (Mid-April to the end of October) 14,000 SF outdoor tiki bar with a shared saltwater pool with swim up bar, outdoor kitchen, and live music. The residences are adjacent to the tiki bar deck and include open layouts, terraces, and custom décor.

Top guest favorite

The living room features comfortable navy sofas with decorative cushions and an ottoman in a warm tone. A lamp stands beside a built-in bookshelf adorned with books and decor. Light streams through the windows, and a decorative fireplace adds to the room's character.

Home in Portsmouth

4.98 out of 5 average rating, 185 reviews

Gorgeous Olde Towne historic home - modern updates

Full of historic charm, modern in all the right places! This 1880s home is located in the heart of Olde Towne Portsmouth, just one block from the Elizabeth River harbor. Walk 3 minutes to the ferry stop and ride across the river to Norfolk's downtown and waterfront restaurants, or walk 5 minutes to Portsmouth's High Street to enjoy Olde Towne's charming coffee shops, restaurants, museums, and theaters. This location is unbeatable!

Top guest favorite

The barn loft is illuminated under the night sky, highlighting its rustic red exterior and decorative features. The front displays large garage doors, flanked by well-maintained landscaping and outdoor lighting. A weathervane sits atop the roof, while an American flag adds a touch of charm to the entrance.

Barn in Suffolk

5 out of 5 average rating, 24 reviews

Cozy Waterfront Barn Loft

Rustic Charm Meets Modern Comfort in Our Barn Loft Retreat Welcome to our beautifully converted hay loft, a serene escape nestled on a former horse farm along the picturesque Chuckatuck Creek. This rustic yet modern loft offers the perfect combination of charm and convenience, making it ideal for family getaways (sleeps up to 8 with pullouts), work trips, wedding weekends, or a peaceful retreat to recharge your soul.