
Holiday rentals in Hampton Roads
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Top-rated holiday rentals in Hampton Roads
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On Beach 3BD+Loft: Sauna|HotTub|Billard|FencedDeck
Wake up to breathtaking Chesapeake Bay views at the Sunrise Retreat, the beach-facing side of our oceanfront duplex. Step directly onto the beach, watch the sky come alive at sunrise, and keep an eye out for pods of dolphins swimming by during the warmer months. Spend your days by the water, then unwind in the hot tub or private sauna. You’ll love the direct private beach access, panoramic bay views, hot tub, sauna, chef’s kitchen, game room with pool table, bar areas, spacious deck and more!
5.0 out of 5 average rating, 63 reviews
All About Amanzi (Water in Zulu)
Recently refurbished and refitted with all the mod-cons our fully equipped townhouse offers you the perfect haven in the heart of Ole Town Hampton and within 30 yards of the Hampton River with its ever changing tranquility. The 2nd floor has an open plan layout with a large deck and water views from every space to make the most of this asset. The 3rd floor has the master bedroom and bathroom with a private balcony for those early morning coffees while watching the changing colors of Amanzi.
4.9 out of 5 average rating, 78 reviews
Wooded Wonderland Miniature Golf Hot tub Pool
Make yourself at home! This property offers a warm and welcoming environment for guests, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!
4.93 out of 5 average rating, 176 reviews
Fully Furnished Home in Hampton 5mins from H Uni
Relax with the whole family at this newly renovated and furnished home. The spacious backyard is a prime spot for family fun. This house can easily sleep 11 people with 7 beds total including a fold-out futon. Enjoy a variety of board games and movies on the TV in every room. Located 10 minutes away from places such as the Hampton Roads Convention Center, Hampton Coliseum, Hampton Virginia Aquaplex, Hampton University, and The American Theatre. *You must be 21 years of age or older to book*
4.94 out of 5 average rating, 152 reviews
*Beautiful Water Views* King Bed*Fast WIFI
Do you desire Peace, Quiet & Tranquility? This townhome is the PERFECT getaway! It's RIGHT on the water and features the following: *Newer Furnishings! *Blazing Fast Panoramic WIFI & Dedicated Workspace *Bedroom 1: KING size bed overlooking the water. Not a bad way to wake up?!? *Gourmet Kit w/Granite Countertops, Stainless Steel Appliances, complete w/a Convection Oven & Coffee Maker & Creamers * Smart TVs w/Adjustable Wall Mounts for your view preference, in Each Bedroom & Living Room.
4.98 out of 5 average rating, 115 reviews
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.
4.96 out of 5 average rating, 599 reviews
Comfy 3 Bedroom Hideaway Minutes From H.U. & Beach
Welcome To Our Place! Ideal For Family Trips, Traveling For Business, Staycations Or Baecations In The Downtown Hampton Area. The Home (Unit A) Is Equipped With Complimentary WiFi, 65” Smart TV, Fully Stocked Kitchen, Coffee Bar, Washer & Dryer! Walking Distance To Restaurants & Nightlife! 5 Min: Buckroe Beach Fort Monroe Hampton University 15 Min: Norfolk International Airport Norfolk Premium Outlets 25 Min: Busch Gardens Williamsburg Water Country USA Virginia Beach Oceanfront
4.9 out of 5 average rating, 131 reviews
4BR Oasis: Your Home Away
Uncover the allure of our 4-bedroom retreat, steps from dining and entertainment. Thoughtfully designed with a fully equipped kitchen, inviting living spaces, and an amazing master bedroom. Proximity to Buckroe Beach, Busch Gardens, Boo Williams Sportsplex, Hampton Waterplex, and the historic charm of Williamsburg awaits your adventure. Let us tailor your stay with personalized recommendations. Welcome to your expansive haven, where every corner is crafted for your enjoyment!
4.79 out of 5 average rating, 125 reviews
Family Holiday House. Events and Beaches Nearby
Large comfy 5BR/3BA home in established neighborhood w/Roku TV & high speed internet! Near Buckroe Beach, Hampton Coliseum Event Center, NASA, Langley Air Base, Boo Williams Sports Arena and Newport News. Also near Virginia Beach, Williamsburg and Busch Gardens There are many parks for recreation. We have a large enclosed porch for lounging. The front entry has an easy wheelchair ramp. Restaurants galore and endless shopping. NEAR AIRPORTS in Newport News and Norfolk.
4.86 out of 5 average rating, 419 reviews
Perfect Getaway!
Home away from home!! Beautiful 2 story house with 3 bedrooms, 3 bathrooms, and a huge playroom over the garage. The master suite has a beautiful bathroom with a jacuzzi tub, and huge walk in shower. The fenced in backyard has plenty of space to run around, and has an awesome saltwater inground pool for fun! In addition, there is a 2 level, new deck, and patio furniture to sit and relax on. There is something for everyone to do here.. I’m positive you will love it!
4.85 out of 5 average rating, 117 reviews
Life on a Sandbar right on Chesapeake Bay
Two bedroom, two bath cottage located on Willoughby Beach right on the shore of the Chesapeake Bay. Centrally located between Williamsburg, Jamestown, Hampton, and Norfolk, Virginia Beach, and the Outer Banks. Close to Norfolk Naval Bases and Old Dominion University. Great for surf fishing or pier fishing on nearby Ocean View Fishing Pier and Restaurant. THIS PROPERTY CANNOT BE RENTED THOUGH CRAIGSLIST!!! DON'T BE SCAMMED!!!
4.98 out of 5 average rating, 112 reviews
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.
4.99 out of 5 average rating, 417 reviewsPopular amenities for Hampton Roads holiday rentals
Other great holiday rentals in Hampton Roads

*NEW* Cozy & Very Stylish home for your family!
5.0 out of 5 average rating, 42 reviews
Charming Oasis: A Quaint Retreat
4.86 out of 5 average rating, 80 reviews
Stunning Cottage in Historic Village
4.99 out of 5 average rating, 93 reviews
Sandy Serenity - On Beach- No Pets
4.95 out of 5 average rating, 97 reviews
Boho beach house w/foosball & patio
4.95 out of 5 average rating, 102 reviews
Prime Downtown 2BR/2BA Near Hampton U & Waterfront
4.74 out of 5 average rating, 667 reviews
4 Bedroom House 5 Minutes from Both Beaches
4.84 out of 5 average rating, 167 reviews
Historic Carriage House at the Church Point Manor
4.98 out of 5 average rating, 181 reviewsDestinations to explore
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- Virginia Beach Oceanfront
- Chesapeake Bay
- Busch Gardens Williamsburg
- Buckroe Beach
- Carova Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Old Dominion University
- Norfolk Botanical Garden
- Regent University
- First Landing Beach
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- The Mariners' Museum
- The Military Aviation Museum
- Back Bay National Wildlife Refuge-N
- Town Point Park
- Nauticus
- Chrysler Museum of Art
- Hampton University
- Virginia Living History Museum





