House holiday rentals in Hampton Roads

4.96 out of 5 average rating, 282 reviews

Home in Smithfield

Mason Manor - Downtown Smithfield next to WCP

Historic Smithfield 233 S Mason Street 2 Bedrooms 1 Bath Located in the heart of historic Smithfield boasts old world charm and character with a touch of today’s conveniences. The living room has gas fireplace for cool evenings & leads to dining area & updated fully equipped kitchen. The full bath is updated with jetted tub. Front porch swing for relaxing and back deck for entertainment. Windsor Castle Park just steps away. Located just around the corner from restaurants, shopping & more.

4.96 out of 5 average rating, 136 reviews

Home in Gloucester Point

Charming coastal home w/ outdoor area and river views

Tucked away at the end of a quiet road, our home welcomes you. This spacious, thoughtfully designed 1 BR/1.5 BA home on 4 acres is ideal for those looking to relax and get away from it all while still being just minutes away from some of the areas best dining and attractions. Whether you want to watch the sun rise over the York River, spend the day exploring the Williamsburg historic triangle (Busch Gardens), or just take it easy around the house and enjoy the outdoor area, the choice is yours.

4.87 out of 5 average rating, 110 reviews

Home in Portsmouth

Penny’s Palace 1 Bed/1 Bath Home

Welcome to Penny’s Palace! A charming home nestled in quiet community of Portsmouth, VA. Entire home for you with sectioned off suite and bathroom. Penny’s Palace is vibrant & elegantly furnished yet practically designed to sleep 2 people comfortably. This bungalow offers an outdoor sitting area with a dreamy lighted canopy & outdoor grill. It’s perfectly located minutes from major Hampton Roads attractions: Olde Town Portsmouth, Children’s Museum, Downtown Norfolk, Casino, and Virginia Beach.

Home in Gloucester Courthouse

4.97 out of 5 average rating, 318 reviews

"Bee-Z Haven" Waterfront Cottage on the Ware River

Curious about what makes Gloucester so wonderful? Live like a local at this Upscale Waterfront Retreat and find out for yourself why renters say "Enjoy the Breath Taking Views". Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our area is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

4.98 out of 5 average rating, 123 reviews

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

4.84 out of 5 average rating, 114 reviews

2-Bedroom Beach Bungalow

Two-bedroom condo across the street from the beach. Closest beach access 1 block down, or vacant lot to access beach across the street. Access to house via 1 set of stairs, no elevator. Heat/AC, dishwasher, w/d, and deck. Linens, bath towels, beach chairs, toys, and towels provided. Quiet family beach, bay water is calm- perfect for children. Close to Norfolk military bases and ODU, EVMS, NSU, Virginia Wesleyan, Hampton University. Approx 25 min from downtown Virginia Beach and Williamsburg.

4.89 out of 5 average rating, 117 reviews

Home in Hampton

Home-Sweet-Home

ADORABLE RANCH-STYLE-HOME! ONLY 1.5 Miles to Buckroe Beach! FIRE-PIT OUT BACK GARAGE w/ WORKOUT SPACE HAVE a great time at this adorable 3BR 1BA ranch home with large detached garage. Fully Renovated and Fully Furnished. Kitchen features new cabinets, stainless steel appliances and opens to family room. New flooring. Nice neighborhood. Ceiling fans throughout. Garage with workout bench and dumb-bells. Back yard with sail-shade, chairs, grill and fire-pit. Make this your GETAWAY home!!!

4.85 out of 5 average rating, 167 reviews

Spanish Style Casita • 2BR/2BA • Dogs Welcome

✨ Welcome to Casita on Granby! ✨ Enjoy a short drive to the beach (less than 2 miles, about 5 minutes), restaurants, grocery stores, and easy nearby highway access to downtown Norfolk, Virginia Beach, and Hampton! We LOVE pups! 🐶 Bring your 4-legged best friend along to bask in our fenced backyard. Must be pre-approved, and additional fees apply. Please read the house rules for additional info. Your perfect getaway is waiting at Casita on Granby. Book now for a stay you won’t forget!

5 out of 5 average rating, 123 reviews

Quiet East Beach Bungalow, 1 block to beach!

Brand new construction located exactly one block from the beautiful Chesapeake Bay at East Beach in Oceanview! A quick walk to the beach or Bay Oaks Park, this bungalow is perfect for relaxing getaways. Fireplace, patio, grill, spacious front porch, new appliances, washer/dryer, private off-street parking. A quick trip to the Naval Bases! Guests are provided with linens, towels, toiletries, and high speed internet(SmartTV). Additional rooms available case by case basis. Please ask.

5 out of 5 average rating, 103 reviews

Charming & Cozy Getaway Steps to Beach/Shops

Escape to The Peche Beche and find everything you need for a relaxing & fun-filled stay! Situated just blocks from the Ocean View beach on the Chesapeake Bay and steps from local favorites, shops, & grocery. You'll find everything you need for the beach, kiddos, pups, remote work, relaxing, feasting, and restful sleep to recharge & enjoy all that Norfolk has to offer! Life’s a peach at the beach! You won't want to leave the coziness and charm as you create unforgettable memories here!

5 out of 5 average rating, 102 reviews

Home in North

The Llama House

Located half-way between Mathews and Gloucester on the beautiful North River with views of the Mobjack Bay, New Point Comfort Lighthouse and Gloucester Point. The ideal spot for anyone needing to reconnect with someone, nature, or themselves. Enjoy fishing, crabbing, kayaking, playing corn hole, birdwatching, napping in a hammock, sipping wine, grilling out, amazing sunsets, listening to old records, playing the ukulele, and other simple pleasures of days gone by.