Holiday rentals with a pool in James City County

A cozy bedroom features a king-size bed with crisp white linens and decorative pillows. A large window offers a view of a green space beyond, with a sitting area including a chair and small table. A 50" TV and coffee station are positioned on a wooden dresser.

4.93 out of 5 average rating, 182 reviews

Kingsmill 1bed/1ba on Golf Course 9th Fairway

This beautiful 1 bed-1 bath unit is a cozy 400 sq.ft. and is located in the exclusive Kingsmill neighborhood. This first floor unit offers a king-size bed with a private patio that walks out onto the 9th Fairway of the River Course at Kingsmill. You'll enjoy the luxurious full bathroom with shower/tub combination and upgraded finishes. In the bedroom, you'll also find a computer desk, an over-sized sitting chair, a mini-fridge, a microwave, a Keurig coffee maker, and 50" Roku Smart TV w cable!

The exterior of a charming three-story building is showcased, featuring red brick walls and a steeply pitched roof. Large windows with white railings overlook a landscaped courtyard with fountains and blooming trees, creating a welcoming ambiance surrounded by greenery.

4.96 out of 5 average rating, 47 reviews

Marriott's Manor Club Ford's Colony 2BD Villa Slee

Discover for yourself where the United States began. Surrounding your resort are some of the most iconic spots in our nation's glorious past, including Yorktown and the amazing Jamestown Settlement replica, where costumed historical interpreters describe and demonstrate daily life in pre-Revolutionary War America. Williamsburg also offers fun modern-day attractions for the whole family. Thrill to fantastic rides at the Busch Gardens Williamsburg theme park, or cool down at Water Country USA.

An overhead view showcases the expansive resort area, featuring a large swimming pool surrounded by lounge chairs. Nearby, a mini-golf course with vibrant green turf and multiple holes is visible. Tennis courts are located at the far side, surrounded by lush landscaping.

4.93 out of 5 average rating, 27 reviews

Family-friendly 1BR/1BA condo @ Kingsgate

Welcome to our charming 1BR/1BA condo close to Williamsburg! Located just minutes from historic Williamsburg, you can explore the area or stay on property and relax by the pool and enjoy the many family-friendly amenities on site. Experience all that Williamsburg has to offer from historic landmarks along one of Williamsburg's many walking and biking trails like Powhatan Creek Trail, Historic Jamestown Bike Trail, and Freedom Park, historic downtown Williamsburg, and Busch Gardens.

Top Guest favourite

A lush field is filled with blooming yellow flowers under a clear blue sky. In the background, a red barn is situated near a fence, surrounded by trees that provide a natural border to the landscape.

Farm stay in Williamsburg

4.97 out of 5 average rating, 381 reviews

3 BR Cottage on Mallardee Farm in Williamsburg

Enjoy all the comforts of home during your Williamsburg vacation at Mallardee Farm! Allow us to make our home, your home while you explore all of Williamsburg’s attractions-just a 15 minute drive away! You’ll find that Mallardee Farm will serve as its own attraction with our friendly, rescued farm pets, walking trails through the 57 acre property, complimentary fishing poles, canoe, row boat & kayaks to use on our 7 acre pond. Covid-19 precautions followed.

Superhost

Two figures in historical military uniforms with distinctive red coats are shown standing together. The background features a building with a bright sky, while a British flag is visible nearby, suggesting a reenactment or historical event.

4.75 out of 5 average rating, 130 reviews

Great family vacation resort condo. Sleeps 12.

Welcome to Greensprings Vacation Resort. We combine two adjacent 2BDR/2BA units to create one huge 4BDR unit with 2 full kit/dining and 2 LR, each with a queen sofa sleeper. And we are near everything! Busch Gardens 7 miles (10-15 minutes) Colonial Williamsburg 5 miles (8 minutes ) Water Country USA 7 miles (10-15 minutes) Historic Jamestowne 5 miles (8 minutes) Newport News/Williamsburg International Airport 19 miles (30 minutes)

Top Guest favourite

A serene outdoor seating area is nestled among colorful autumn leaves, with four adirondack chairs arranged around a wooden platform. The setting sun casts a warm glow over the peaceful view of Bland Creek and the marsh, enhancing the natural beauty of the landscape.

Guesthouse in Gloucester

5 out of 5 average rating, 150 reviews

The Bluebird — Waterfront, Pool, Dock & Firepits

With stunning views overlooking Bland Creek, this guesthouse is the perfect place to unwind or start your adventure. This two-bedroom apartment is nestled high in the treetops, perfectly situated on 10 acres of wooded and coastal beauty. When the time comes to explore, guests are only minutes away from eclectic shopping and dining in historic downtown Gloucester, with Williamsburg and Richmond an easy 45 minutes away.

The historic manor house, built in 1735, features a robust brick exterior with large windows and a slate roof. Lush green gardens and flower beds surround the structure, complemented by a winding brick pathway leading to the entrance.

5 out of 5 average rating, 10 reviews

3 Bedroom Suite in Historic Williamsburg!

Step back in time at The Historic Powhatan Resort, located on 256 acres of rolling woodland hills in historic Williamsburg, Virginia. Bring the whole family to this great place with lots of room for fun • Guest checking in must be 21+ with valid ID. • Guest must have debit/credit card to put $100 refundable security deposit on hold at resort check-in. • Name on reservation must match photo ID at check-in..

4.93 out of 5 average rating, 110 reviews

A serene river view is captured at sunset, showcasing vibrant hues of orange, pink, and purple across the sky. A wooden pier extends into the water, backed by silhouetted trees. The calm surface reflects the colorful sky, creating a tranquil atmosphere.

Guesthouse in Gloucester

Clay Bank River Front Cottage

Recently updated waterfront cottage 2 bedroom - 2 queen beds, a pull out sofa, 28 private acres on the York River in Gloucester, Va. Great remote getaway with a pool, kayaks and private pier for fishing/crabbing. Lightly traveled river. Access to Yorktown, Newport News, Williamsburg, Jamestown, Richmond, Norfolk, Urbanna. Shares the property with the main house where owner lives.

The exterior of the building displays a welcoming layout, featuring multiple covered porches and classical architectural elements. Lush landscaping surrounds the entrance, with well-maintained shrubs and trees complementing the brick facade. The sky adds a soft evening glow to the scene.

4.83 out of 5 average rating, 29 reviews

Governor’s Green 1BR Dlx Condo w/ Full Kitchen

Everything needed for a memorable getaway to historic Williamsburg is right here. Take advantage of on-site recreation and endless amenities in a picturesque setting. The well-manicured lawns and pristine lakes make a lovely retreat after a day of adventuring in Colonial Williamsburg. This suite includes a King bed, and a Queen sleeper sofa in the main living area.

Superhost

An aerial view captures the expansive outdoor recreational area, featuring two swimming pools, a miniature golf course, and well-maintained tennis courts. Surrounding landscaped greenery enhances the inviting space, with lounge chairs positioned around the pools for relaxation and enjoyment.

4.85 out of 5 average rating, 41 reviews

Wyndham Kingsgate, 2 BR Deluxe

Located just 5 minutes from historic Williamsburg, Club Wyndham Kingsgate provides convenient access to historic attractions, wineries, beaches, and local artisan shops. Relax by the pool or indulge in the natural splendor surrounding this charming resort. Experience scenic vistas and historic landmarks along one of Williamsburg's many walking and biking trails.

A resort pool area is depicted, featuring a vibrant blue swimming pool surrounded by lounge chairs. The brick building in the background is characterized by rows of windows and a variety of green umbrellas, set against a clear blue sky.

4.85 out of 5 average rating, 170 reviews

Westgate Historic Williamsburg One Bedroom

Offering a one bedroom apartment in Westgate Historic Williamsburg Resort with a king size bed, sofa bed and full kitchen. This fabulous resort has fantastic amenities and is a great location to visit the area attractions such as Colonial Williamsburg, Busch Gardens Williamsburg and Water Country USA. A great location to visit the local attractions.

A row of well-maintained townhouses is situated in a green landscape. Lush bushes and manicured lawns frame the buildings. A flowering tree adds color to the scene under a bright blue sky with scattered clouds.