Vacation rentals in Bennett Harbor

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Top-rated vacation rentals in Bennett Harbor

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

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Top guest favorite

A modern kitchen features light cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator, oven, and dishwasher, are visible. Soft lighting highlights the spacious layout, which is complemented by tiled flooring and a seamless flow into the adjacent dining area.

Home in Portsmouth

5 out of 5 average rating, 102 reviews

Hidden Gem.4/bedroom cozy home fenced in yard

Make yourself at home!Hidden Gem offers a clean welcoming space for guests, located in a quiet established neighborhood. Guests should expect a clean and comfortable stay. Conveniently located near parks,shopping, and dining options. Attractions aren’t too far away Rivers casino.2.9. Virginia Beach Ocean Front.23miles. Waterside district Norfolk 8.5 miles. Town center 17.miles. Busch Gardens 40 miles. Old Dominion University 9.8 miles. Norfolk State University 8.8 miles.Hampton University23miles

Guest favorite

A couple relaxes on the deck of the sailboat, enjoying drinks against a vibrant sunset backdrop of pink and purple hues. Soft blankets and a cozy atmosphere are present, with the marina and boats gently reflected in the calm water.

Boat in Norfolk

4.94 out of 5 average rating, 133 reviews

Romantic Sailboat Experience + Seafood Restaurant

We can't adequately describe how romantic & carefree it feels to step aboard our sail boat. The perfect stay begins by treating yourselves to dinner at the marina's seafood restaurant, then snuggle up together on deck to watch the sunset turn the sky pink & purple. The marina atmosphere is simply magical & you'll love rocking with the gentle sway of calm waters. Come enjoy a weekend aboard this amazingly cozy & romantic sail boat. Convenient to Norfolk & Virginia Beach, the location is prime!

Guest favorite

A bright living area is featured with a modern kitchen, including white cabinetry and granite countertops. A comfortable gray sofa is positioned opposite a wall-mounted TV, complemented by colorful throw pillows. Large windows allow natural light to illuminate the space.

Guesthouse in Suffolk

4.91 out of 5 average rating, 122 reviews

The Magnolia Guesthouse With A Private Entrance

This special place is close to everything, making it easy to plan your visit. Within walking distance to places like Chick-fil-A, Texas Roadhouse, Kroger, Food Lion and more. You’re about 20-30min from all surrounding cities. The studio includes keyless entry, in unit washer and dryer, full kitchen, queen size Murphy bed, and a 50in smart tv. We also have a level 2 charger for our electric car travelers. Linens and towels will be provided as well. Allow us to make your experience a great one!

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

4.96 out of 5 average rating, 132 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 serene view of a calm waterway is presented, featuring a long pier extending into the horizon. Gentle ripples reflect the blue sky dotted with fluffy white clouds. The landscape around the water includes patches of grass, enhancing the tranquil atmosphere of the setting.

Townhouse in Hampton

4.98 out of 5 average rating, 108 reviews

*Beautiful Water Views* King Bed*Fast WIFI

Do you desire Peace, Quiet & Tranquility? This townhome is the PERFECT getaway! It's RIGHT on the water and features the following: *Newer Furnishings! *Blazing Fast Panoramic WIFI & Dedicated Workspace *Bedroom 1: KING size bed overlooking the water. Not a bad way to wake up?!? *Gourmet Kit w/Granite Countertops, Stainless Steel Appliances, complete w/a Convection Oven & Coffee Maker & Creamers * Smart TVs w/Adjustable Wall Mounts for your view preference, in Each Bedroom & Living Room.

Guest favorite

A cozy living space features a light-colored sofa with blue cushions and an armchair. A wooden coffee table sits on a patterned rug, accompanied by two lamps providing soft light. Artwork adorns the walls, and a small plant adds a touch of greenery.

Apartment in Portsmouth

4.94 out of 5 average rating, 131 reviews

Lovely Two Bedroom, 1 1/2 bath, King bed Townhouse

Your family will be close to everything when you stay at this centrally-located place. Beautiful re-done townhouse. New carpet and luxury vinyl, new vanities and toilets, Maytag washer and dryer, central heat and air, brand new hot water tank, small patio in back. Close to shopping, Kroger, T J Maxx, Walmart, CVS, and other shops. Plenty of take out food, like chick-fil-A, Panda Express, Wendys, Rallys, Dunkin Donuts, and more. Brand new Rivers Casino less than a mile away!

Top 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

4.96 out of 5 average rating, 245 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

4.86 out of 5 average rating, 112 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

4.92 out of 5 average rating, 36 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 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

4.97 out of 5 average rating, 387 reviews

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

Welcome to The Purple Room, where every guest is made to feel like royalty. More than an Airbnb, it’s a one-of-a-kind boutique retreat intentionally designed to create unforgettable memories. From the peaceful atmosphere and thoughtful touches to your private entrance and relaxing escape, every detail has been curated to help you unwind, recharge, and experience something truly special. Come discover The Purple Room experience. 💜

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, 35 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.

Top guest favorite

A vibrant sunset is captured over the water, with shades of orange and pink blending into the horizon. A wooden dock stretches into the foreground, surrounded by evenly spaced posts that rise from the calm water's surface.

Guesthouse in Hampton

4.99 out of 5 average rating, 406 reviews

Sun Sea and Sand

Welcome to Sun Sea and Sand, a Caribbean theme in Hampton, Virginia. Sun, Sea and Sand is a beautiful, waterfront, second story, two-bedroom, one-bath guest house located on a private drive providing lots of privacy including your own private entrance as well as stairs leading from your private balcony directly to the waterfront. High-speed fiber-optic wifi and cable with blue ray player provided.