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!

4.87 out of 5 average rating, 23 reviews

The Serene Retreat; 2 bedrooms & 2 full baths

Make some memories at this unique and family-friendly place, featuring 2 bedrooms with queen beds, 2 baths, a comfortable reading nook, & a pristine kitchen. It is perfect for individual and family relaxation, & less than 14 mins to Busch garden, Colonial Williamsburg, Water park USA, William & Mary college, Governor’s palace, & Jamestown Sightseeing. Only 5 minutes to Sentara Regional, and many shopping malls; Walmart, Williamsburg premium outlets, Ross, etc, making it easy to plan your visits.

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.

The resort features expansive outdoor spaces, including a large pool and a scenic pond with a water fountain. Spacious greenery surrounds the area, providing a serene environment. Multiple buildings, designed with modern architecture, are visible, complementing the landscape.

4.89 out of 5 average rating, 28 reviews

Lovely 1 bedroom suite, GG Williamsburg, VA

Enjoy everything that is wonderful about Williamsburg, Virginia. Relax in this beautiful serene setting including an indoor and outdoor pull, plan a day at the spa, play some games in the activities room, put put or tennis. This suite is located three miles north of historic Williamsburg where you can enjoy walking trails to wineries, beaches, and artisan shops. The location also offers crafts for children, wine and cheese tastings, muffins and mimosas and so much more.

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, 382 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.

An aerial view captures a spacious resort complex overlooking a tranquil pond. The outdoor swimming pool is surrounded by lounge areas, with a fountain creating gentle ripples in the water. Lush green lawns frame the buildings, and rolling hills can be seen in the background.

4.9 out of 5 average rating, 31 reviews

Wyndham Governor's Green, 2 BR Deluxe

The Wyndham Governor’s Green welcomes guests with perfectly manicured grounds and gentle southern hospitality. Softly rolling hills rise to expose placid ponds and tree-lined paths. Guests of the resort have full access to indoor and outdoor swimming pools, hot tubs, and even an adult-only pool. Children are sure to soak the day away at the kids pool and splash zone. Tennis courts, billiards room, and miniature golf will keep you as active as you desire.

A sparkling blue pool is surrounded by a patio featuring several lounge chairs. In the background, a shaded pavilion offers seating and leisure space, with lush greenery visible beyond the pool area, creating a welcoming atmosphere for relaxation.

4.93 out of 5 average rating, 14 reviews

Powhatan Resort- 2 bdrm sleeps 6

This is 2 bedrooms/2 bath fully stocked condo sleeps up to 6 guests . This is a timeshare resort however as our guest you are not required to take a tour. Kitchen and washer/dryer. The master bedroom has a kingsize bed and the 2nd bedroom is either a queen or 2 twins. All ground floor have 2 twins. If you have a preference please let host know. The resort assigns rooms at check in so final decision is at the resort level.

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.

Guest house 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.

Guest house in Gloucester

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.

4.93 out of 5 average rating, 111 reviews

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.

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.