Holiday houses in Bennett Harbor

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Top-rated holiday rentals in Bennett Harbor

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Top Guest favourite
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, 346 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!

Guest favourite
A vibrant bedroom features a full-size bed with a colorful patterned quilt and decorative pillows. Two bedside lamps illuminate the room, and a tapestry hangs on the wall, depicting a historical scene. Wooden flooring and a small table add warm accents to the space.
Apartment in Suffolk
4.93 out of 5 average rating, 15 reviews

Private Guest Suite in Historic house

You will have 2nd floor of historic home to yourself. Completely private and separate from downstairs of house. Suite has own private entrance and own driveway/parking area. Outside sitting/smoking area Includes full size fridge,microwave, expresso maker and drip coffee maker. Along with complimentary bottle of wine and fresh baked muffins for breakfast. Bedroom has very comfortable full size bed and TV with Netflix,Prime Video. Restaurants, parks, lakes nearby. 2 guests for short term stays.

Guest favourite
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
4.93 out of 5 average rating, 116 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 favourite
Condo in Chesapeake
5 out of 5 average rating, 10 reviews

Luxe Cozy Condo in - Western Branch

Come relax and enjoy this cozy stylish newly renovated smart home. This home includes two bedrooms and one bathroom with a fully equipped kitchen and laundry room. The main bedroom has a private balcony. The living room includes a sleeper couch for extra guests. This unit is located on the second floor of a family-friendly condominium community. This home caters to long-term traveling professionals. This home is located near a YMCA, Bowling Alley, Mall, Restaurants, Shops, and Hospitals.

Top Guest favourite
Home in Suffolk
4.92 out of 5 average rating, 12 reviews

Nix Cove Haven

Clean, comfy, private room with a queen bed and entire ground floor in a safe and quiet neighborhood. Enjoy the privacy & comfort of your own space with everything you need to relax after a long day: bedroom with TV, private bathroom, high speed WiFi, coffee bar, fridge, microwave & the added convenience of a washer/dryer. All the modern conveniences of home with the feel of a cabin in the woods. Cozy up and watch a movie by the electric fireplace inside or relax on the deck by the water.

Guest favourite
Home in Portsmouth
5 out of 5 average rating, 15 reviews

The Main House

Welcome to Ary’s House! Relax and unwind at my ranch-style home featuring cozy beds, two full bathrooms, and a dedicated workspace with a sleeper sofa for an extra guest. A fully equipped kitchen and dining area stocked with many of your cooking essentials. For added convenience, a washer and dryer are available in unit. Enjoy the private backyard patio, perfect for grilling out or gathering around the fire pit. Our home is family-friendly, We look forward to hosting you!

Top Guest favourite
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, 107 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 favourite
A two-story garage features a sloped roof and a set of double windows on the upper level. A concrete driveway extends beside it, flanked by greenery and a seating area. Sunlight illuminates the space, enhancing its inviting appearance.
Guesthouse in Chesapeake
4.89 out of 5 average rating, 93 reviews

Western Branch Loft Suite

Enjoy your own space in this quiet studio located near Navy bases, hospitals, and the beach. It’s perfect for those looking for a little bit of peace while they are in the area for work, house hunting, visiting family or friends. This comfy guesthouse is in a safe neighborhood 5 minutes from grocery stores, restaurants, gyms, and highways to get around. Avoid the busiest traffic areas here while still being able to enjoy a day trip to the beach!

Guest favourite
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, 17 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 favourite
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, 21 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.

Guesthouse in Norfolk
5 out of 5 average rating, 4 reviews

The garden house

Cozy 1-bed guest house retreat with heart over perfection. A peaceful, character-filled hideaway for slow mornings, homemade meals, and coffee/tea rituals. Includes a stocked coffee & tea bar and full kitchen. LGBTQ+ friendly stay. Shared backyard with owner (not fully private). 420-friendly outside only—please be respectful and keep all smoking outdoors. Come rest, cook, sip, and belong.

Top Guest favourite
An aerial view depicts the guest suite, nestled among lush greenery, with a spacious swimming pool nearby. The main house, along with various outdoor amenities, is visible, showcasing well-maintained landscaping and open fields surrounding the property.
Guesthouse in Suffolk
4.97 out of 5 average rating, 158 reviews

Country Living Guest House (Upstairs/Downstairs)

This country living guest suite is conveniently positioned on Lone Star Lakes Park. It is located in a quiet, private drive. Prepare quality meals in the down-stairs fully equipped eat-in kitchen with built-in cabinets, spacious countertops, a full-sized fridge, an electric stove, and everything you need to feel at home. Just off the kitchen is a half-bath. NO PETS ALLOWED.

Popular amenities for Bennett Harbor holiday rentals

  1. Airbnb
  2. United States
  3. Virginia
  4. Suffolk
  5. Bennett Harbor