Guesthouse vacation rentals in Chesapeake

BlueBird Nest

Keep it simple at this peaceful and centrally-located oasis, tucked away in coastal Virginia. Our newly renovated 1BR/1BA barn apartment on 3 acres is ideal for those who want to live like a local. We are 3 miles from the heart of the American Revolution in Yorktown, and Yorktown Beach, and a short drive to area attractions in the Historic Triangle. Unwind after a day of exploring with a glass of wine on the balcony or enjoy the firepit and the view. This is an upstairs apartment with stairs.

Charming Quiet Carriage House

Escape to this adorable newly furnished modern apartment on 6 acres. Near amphitheater, PACC, sportsplex, and many shops & great restaurants! 8 easy miles to the beach. Brand new furniture. Refinished hardwood floors. New stainless steel appliances. New queen bed and mattress. New pullout couch to accommodate 2 additional guests. Quiet space surrounded by woods and gardens. The Carriage House is located above a detached garage, private space. Washer and dryer provided. Perfect relaxing getaway!

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.

Cozy country studio apartment

Escape the city and recharge in this serene, thoughtfully designed studio. Enjoy a restful night in the comfortable queen-size bed, and take advantage of the well-equipped kitchenette for easy meals during your stay. Located just 45 minutes from the beach, this retreat makes it simple to spend the day by the ocean, then return to the calm of your private hideaway—away from the crowds, noise, and stress.Whether you’re here to relax, explore, or both, this cozy studio is the perfect home base.

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)

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!

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.

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.