Holiday houses in Hampton Roads

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Top-rated holiday rentals in Hampton Roads

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

A well-appointed bedroom features a spacious bed with a textured white cover. Colorful accent pillows add depth to the decor. A wooden dresser stands against one wall, while a bedside lamp illuminates the space. Natural light filters through a window adorned with light curtains.

Home in Smithfield

4.97 out of 5 average rating, 326 reviews

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.

Guest favourite

A couple relaxes on the deck of the sailboat, enjoying drinks against a vibrant sunset backdrop of pink and purple hues. Soft blankets and a cozy atmosphere are present, with the marina and boats gently reflected in the calm water.

Boat in Norfolk

4.91 out of 5 average rating, 140 reviews

Romantic Sailboat Experience + Seafood Restaurant

We can't adequately describe how romantic & carefree it feels to step aboard our sail boat. The perfect stay begins by treating yourselves to dinner at the marina's seafood restaurant, then snuggle up together on deck to watch the sunset turn the sky pink & purple. The marina atmosphere is simply magical & you'll love rocking with the gentle sway of calm waters. Come enjoy a weekend aboard this amazingly cozy & romantic sail boat. Convenient to Norfolk & Virginia Beach, the location is prime!

Guest favourite

An aerial view of the property reveals a spacious backyard featuring a swimming pool surrounded by lounge chairs and inflatable pool toys. Lush greenery encircles the area, enhancing the sense of privacy, and the house is seen with its inviting deck and patio area.

Home in Portsmouth

4.92 out of 5 average rating, 173 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!

Guest favourite

A serene view of a calm waterway is presented, featuring a long pier extending into the horizon. Gentle ripples reflect the blue sky dotted with fluffy white clouds. The landscape around the water includes patches of grass, enhancing the tranquil atmosphere of the setting.

Townhouse in Hampton

4.98 out of 5 average rating, 110 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.

Guest favourite

A charming studio entrance is framed by lush greenery and flowering plants. A yellow exterior is complemented by a welcoming front porch adorned with climbing vines. A brick pathway leads to the door, inviting guests into a cozy retreat.

Guest suite in Hampton

4.96 out of 5 average rating, 592 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.

Superhost

A spacious bedroom is illuminated by natural light from a large window with soft blue curtains. A cozy seating area features a grey sofa and a round coffee table. The room includes a comfortable bed, dark wood furniture, and decorative wall art, creating a serene environment.

Home in Hampton

4.8 out of 5 average rating, 122 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!

Guest favourite

A two-story cabin made of wood stands beside a serene pond, surrounded by tall pine trees. The cabin features large windows and a spacious deck with rocking chairs, inviting peaceful moments by the water's edge.

Cabin in Cape Charles

4.96 out of 5 average rating, 254 reviews

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

Guest favourite

Home in Newport News

4.84 out of 5 average rating, 116 reviews

The Artist House

Welcome to the Art House! Enjoy stunning local artwork displayed throughout our property which is a perfect blend of comfort & creativity. Our ideal location places you three minutes from the Shipyard, ten minutes from Coliseum Central & Hampton University, & fifteen minutes from Christopher Newport University. You want more! We are twenty five minutes from Norfolk state and ODU. Let’s not forget the beach too! We are fifteen minutes from buckroe beach in Hampton.

Guest favourite

An inviting interior features a spacious bed adorned with soft bedding and decorative pillows. Natural light filters through large windows, illuminating the cozy sitting area with comfortable chairs and a wooden coffee table. Artwork and decorative accents add charm to the welcoming atmosphere.

Guesthouse in Suffolk

4.91 out of 5 average rating, 47 reviews

The Harlequin Cottage

This unique place has a style all its own. Cottages on the Point was launched in 2018 and offers timeless interior styling and stunning resort style outdoor views. The property features a seasonal (Mid-April to the end of October) 14,000 SF outdoor tiki bar with a shared saltwater pool with swim up bar, outdoor kitchen, and live music. The residences are adjacent to the tiki bar deck and include open layouts, terraces, and custom décor.

Top Guest favourite

The Purple Room features a spacious bed with white linens and purple accents. A cozy seating area is visible beside large windows with light filtering through sheer curtains. Decorative elements, including wall art and a soft purple rug, enhance the vibrant atmosphere.

Guest suite in Chesapeake

4.97 out of 5 average rating, 392 reviews

Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!

Welcome to The Purple Room, where every guest is made to feel like royalty. More than an Airbnb, it’s a one-of-a-kind boutique retreat intentionally designed to create unforgettable memories. From the peaceful atmosphere and thoughtful touches to your private entrance and relaxing escape, every detail has been curated to help you unwind, recharge, and experience something truly special. Come discover The Purple Room experience. 💜

Superhost

Home in Norfolk

4.83 out of 5 average rating, 197 reviews

Norfolk Beach Casita | Fenced Yard | Dog Friendly

🏡 Unique Spanish-style Norfolk vacation home 🐶 Dog-friendly stay with fenced backyard 🌿 Private patio and outdoor seating area 🛋 Bright living room with vaulted ceilings 🍽 Open dining space perfect for gathering 🍳 Full kitchen for easy home-cooked meals 🚗 Easy access to highways and downtown Norfolk 🌊 Less than 2 miles from the beach 🛒 Close to grocery stores and restaurants 👨‍👩‍👧 Comfortable space for up to 4 guests

Top Guest favourite

An aerial view showcases a beach cottage with a white roof situated near a sandy shore. The beach is visible with gentle waves lapping at the coastline. Surrounding vegetation and neighboring homes are seen, enhancing the coastal ambience.

Cottage in Norfolk

4.98 out of 5 average rating, 108 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!!!