Family-friendly holiday rentals in Hampton Roads

Storybook Cottage

Beautiful studio within walking distance to downtown Hampton waterfront, marinas, shopping, dining, microbreweries, arts & museum district. Short drive to beaches, NASA/Langley AFB, Hampton U., and Ft. Monroe. Centrally located off I-64 between Williamsburg and Va. Beach. Quiet and cozy. Has private front and rear entrances and covered private back porch. Perfect for couples & business travelers. Complimentary coffee, tea , water, etc. No 3rd party reservations. Self check in after 3 pm.

Moody Modern:Hot tub, Tile Shower, Fire Pit, Views

Escape to this beautifully remodeled guest cottage, designed for an unforgettable stay. Nestled in a serene 6.5-acre setting with private creek views, it's just minutes from shopping, breweries, and dining. Wake up to breathtaking scenery, unwind in a peaceful setting, and enjoy modern amenities. Relax by the fire pit or soak in the hot tub. Perfect for a romantic retreat or a fun-filled family getaway in the Historic Triangle. Unmatched comfort, charm, and relaxation—your perfect escape awaits!

Guesthouse at Vessel Farm & Winery, Waterfront

Just 5 miles from Cape Charles and 30 minutes from Virginia Beach, our contemporary Guesthouse gives you the peace and solitude characteristic of the Eastern Shore along with the convenience of being close to town. Our twenty acre waterfront farm, home to both a Vineyard and an Oyster Farm, has plenty of nearby walking or biking and a dock on a secluded arm of the Chesapeake Bay. Our farm is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

Romantic Sailboat Experience by Seafood Restaurant

We can't adequately describe how romantic & carefree it feels to step aboard our sail boat. After a wonderful meal at the marina seafood restaurant our guests love to snuggle up together on deck and watch the sunset turn the sky pink & purple with a glass of bubbly. The marina atmosphere is simply magical & you'll love sleeping to the gentle sway of calm waters. Come enjoy a night aboard this amazingly cozy & romantic sail boat. Convenient to Norfolk & Virginia Beach, the location is prime!

Near Beach Eclectic Retreat

Unwind in our urban oasis: a 2-bed, 1-bath apartment moments from dining, shops, and entertainment. Your comfort is paramount, with a fully equipped kitchen, cozy living space, and a pull-out sofa. With proximity to Virginia Beach, Portsmouth Casino, Buckroe Beach, Busch Gardens, Boo Williams Sportsplex, Virginia Beach Sportsplex and Hampton WaterPlex, your dream vacation is at your doorstep. Count on us for personalized suggestions to elevate your stay. Welcome to the ultimate city retreat!

One block from the Beach

Stay at one of the highest rated homes in Willoughby Beach. It has everything you need to have a relaxing getaway. Enjoy the breezes of the Willoughby Bay on the back 2 decks, and the Chesapeake Bay on the front 2 decks. 500 ft walk to Chesapeake beach access, and an outdoor shower ready when you return. We have been hosting since 2018 and you can read our reviews to see that this property is our pride and joy. Let us show you what a five star experience is on Airbnb... Mandy and Kevin

"Shangri-La", of Hampton, Virginia

2nd story 1200 square foot apartment with 2 BR's, Wi-Fi, microwave, fridge and bar with sink. Walk in glass enclosed shower & soaker tub. Private deck with gas grill down the spiral stairs below on ground level patio. Pool table in BnB. We share our pool with our BnB guests seasonally. Please inquire about pool availability if important to your booking. Local history, sites, nature and beaches abound. Security cameras surround the exterior of our home for our protection as well as yours!

*No Cleaning Fee*The Pirate's Cove~Lux Furnishings

Welcome to Pirate’s Cove! Just over the bridge from the home of The Pirates of the illustrious HAMPTON UNIVERSITY! *Great walk-able location to all of downtown's restaurants & features the following: *Brand New Carpet* Fresh paint* Premium Luxury Furnishings/Bedding *2 Designated work spaces/desks on each level w/Super Fast WIFI Internet *Fully Equipped Eat In Kit w/Seating for 6-8 *A Coffee/Tea Bar Note:King Bed can also be a single(2 Twin Mattresses)

Sojourn Guest House: Buckroe Beach Suite B

The Sojourn Guest House at Buckroe Beach are short term rentals located in the Buckroe Beach Neighborhood of Hampton, Va. The house is located in a quiet neighborhood just a 10 min walk/2 min drive to the newly renovated Buckroe Beach. The property has a large back yard and the house makes for a cozy stay with one bedroom suite, one bathroom, enclosed patio great for a morning cup of coffee or a relaxing evening.