Guesthouse vacation rentals in Chesapeake

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!

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.

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.

The Dismal Loft

Indulge in serenity at our 1 bedroom, 1 bath detached garage loft. Just 5 minutes from Dismal Swamp State Park's extensive trails and 20 minutes from the historic, waterfront downtown of Elizabeth City. For beach lovers, VA Beach Oceanfront is only 45 minutes away, with OBX just an hour's drive. Whether you're an outdoor enthusiast, a traveler seeking a peaceful retreat, or your in-laws are visiting and your home is just not "big enough" for them to stay, our loft is your perfect haven.

Peaceful, Private Studio Apartment.

Kick back and relax in this calm, stylish space. Located in a very peaceful neighborhood. Completely Detached Garage apartment 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 hybrid mattress, huge shower, wifi, netflix, surround sound, everyone loves it! Plus a nice private outdoor space with fire pit and lighting. (fenced in)

Country Escape - Next DOOR - Hidden Gem

Take it easy at this unique and tranquil getaway in the country! This 1100sf rental is above a four car garage in the backyard of the “Country Escape” short term rental. The deck overlooks the serene “park like” backyard in the woods surrounded by trees so you feel like you are in a treehouse. The décor is very comfortable and welcoming. We named it "Next Door" due to the repurposing of old doors. It is the perfect location for you to hide away and relax while you are in the area.

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.

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.

Panoramic river view retreat

Located in the heart of Western Branch, this 3-bedroom 2 bath 2100 square foot guesthouse is located on the 2nd floor of this lovely home nestled up to a full panoramic view of the Elizabeth River. Whether you are needing a quiet place to work, a place to reset while watching the sunset on the balcony or making smores at the firepit with your family, The Cove has something for everyone.