Guesthouse vacation rentals in Chesapeake

4.92 out of 5 average rating, 12 reviews

Guesthouse in Norfolk

Garden Retreat

Property is close to the bay (2.5 miles) and is on a 0.6 acre lot with dozens of old, mature trees. There is a patio/sitting area among the trees that creates a peaceful getaway. The unit is spacious, with a queen bed, large TV and sitting area, and a desk/workspace that looks out at the trees. Kitchen is full sized. Bathroom is also full sized with a beautiful tiled shower. It feels like a peaceful oasis you will not want to leave, but when you do...you'll end up in another paradise by the bay!

LocationQuietLayout

A spacious upper-level room features a large bed with a light-colored blanket. Natural light enters through two windows, and artwork is hung on the walls. A dining table with black chairs and a small sitting area are visible, creating a cozy and functional living space.

4.97 out of 5 average rating, 69 reviews

Peaceful, Private Studio Apartment.

Indulge yourself in this calm, stylish space. With a king size bed Located in a very peaceful neighborhood. Completely Detached guesthouse on a wooded 3 acre lot, extremely private and extremely quiet, very nice neighborhood, very safe with a 1 mile walking path. Shaded parking spot for two vehicles.. brand new ice cold air conditioning, brand new king size hybrid mattress, huge shower, wifi, netflix, surround sound, everyone loves it! Plus a nice private outdoor space with fire pit and lighting

FamilyLocationWalkability

4.91 out of 5 average rating, 126 reviews

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

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!

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Guesthouse in Downtown Norfolk

A bright sleeping area features a spacious bed with light blankets, accented by a decorative throw. A large circular window allows natural light to fill the space, complemented by dark curtains. A cozy armchair sits nearby, enhancing the room's inviting ambiance.

4.97 out of 5 average rating, 711 reviews

Private Guesthouse, Ghent/Downtown near ODU, EVMS

Legally licensed and permitted with the City of Norfolk! We did it right here! European-style guesthouse between Ghent and the Heart of Downtown. Walking access to many restaurants and hotspots, and across from “The Tide” light rail, and YMCA, Chrysler Museum of Art, Granby St, Colley Ave, EVMS, Town Point Park! 15-min from the ocean. FREE PRIVATE PARKING: designated driveway parking spot; Kitchenette includes– cooktop, sink, microwave, coffee, fridge; Wifi, separate HVAC, bath, FREE laundry.

ValueFamilyLaundry

Guesthouse in Virginia Beach

A rustic stone fireplace serves as a central feature in the living area, its warm glow inviting relaxation. The high ceiling and exposed beam accents create a spacious atmosphere, complemented by hardwood flooring and comfortable seating arrangements nearby.

4.91 out of 5 average rating, 67 reviews

The Sportman's Lodge

The Sportsman’s Lodge is a rustic and relaxing modern getaway with all the conveniences you are accustomed to but surrounded by the gorgeous Back Bay Wildlife Refuge. Enjoy the relaxing countryside at this waterfront property, while still being only a short drive away from Sand Bridge Beach. If you are looking to get away from the standard Virginia Beach Boardwalk tourist experience and get back to nature, this is the place for you. Free kayaking to Back Bay, access to fishing and crabbing.

FamilyLocationPets

The lodging room features a spacious bed with neutral-colored linens alongside a comfortable armchair and an ottoman. A wooden dresser and wall-mounted lamps provide illumination. Decor accents include art and a cozy area rug, creating a welcoming environment.

4.99 out of 5 average rating, 84 reviews

Country Escape - Next DOOR - Hidden Gem

Relax at this tranquil country retreat! This 1,100 sq ft loft sits above a garage behind the main Country Escape rental. The deck overlooks a wooded, park-like yard, giving it a cozy treehouse feel. Thoughtful décor and repurposed doors (the inspiration for its name, “Next Door”) create a welcoming space. Perfect for unwinding and recharging while still close to local attractions. From the time you walk in you will feel the warmth and comfort of a country escape.

LocationFamilyNearby

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.

4.92 out of 5 average rating, 130 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!

ValueFamilyComfort

4.93 out of 5 average rating, 28 reviews

A spacious sleeping area features a luxurious king size bed adorned with decorative pillows. A comfortable sofa and armchair provide additional seating, complemented by a wooden coffee table and a green plant. Natural light fills the room through large windows, offering views of the serene outdoor surroundings.

Guesthouse in Suffolk

The Pintail Cottage

Kick back and relax in this calm, stylish space. 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.

FamilyValueRiver

The exterior of a two-story brick apartment building is shown, featuring a staircase leading to the entrance. Lush green shrubs and trees frame the entrance, while a driveway accommodates two blue recycling bins. A neighboring structure is visible to the left.

4.98 out of 5 average rating, 261 reviews

Beautiful and Chic Studio Apartment

Chic private apartment is located in a quiet neighborhood at the end of the peninsula were the Indian River flows into the Elizabeth River. Centrally located, we are nestled in the heart of Hampton roads with Virginia Beach 1 mile to the east and Norfolk 1 mile to the north. Twenty minutes from everywhere you'll want to go: the airport, the beach, multiple shopping centers and several universities.

FamilyLocationTV

4.99 out of 5 average rating, 411 reviews

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

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.

FamilyValueAmenities

4.95 out of 5 average rating, 22 reviews

Guesthouse in Norfolk

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.

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