Guest house holiday rentals in Chesapeake

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.

New Coinjock guesthouse w/elevator, kitchen & W/D

Nestled in charming Coinjock, this newly built unit offers a perfect blend of comfort and coastal charm. Guests can use the elevator or front entry doors to enter your private and secure space on second level. This suite provides everything needed for a relaxing escape. Enjoy a fully equipped kitchen, a cozy bedroom and modern amenities including AC, WiFi and a washer/dryer. With stunning views of the Corolla lighthouse and ample parking, you'll find it easy to unwind and savor your stay.

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.

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 or house hunting. 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!

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.