Vacation rentals with a pool in Williamsburg

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Top-rated rentals with a pool in Williamsburg

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite
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.
Condo in Williamsburg
4.93 out of 5 average rating, 178 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!

Guest favorite
Two classic white Adirondack chairs are positioned on a grassy bank overlooking the calm water of the Rappahannock River, framed by gently swaying trees. The sky displays a soft transition of colors as the sun sets, creating a serene and inviting view.
Home in Locust Hill
4.97 out of 5 average rating, 152 reviews

Waterfront Cottage Getaway Views/Kayaks/Fire Pit

A timeless cottage on a quiet property on the Rappahannock River with charming rose garden, relaxing pool, and quintessentially Virginia feel. Find us on IG @rosehilllcottagerappahannock! Explore nearby towns of Urbanna, White Stone, and Irvington, or stay close to home to enjoy sweeping views, waterfront adirondack chairs, and kayaks — perfect for a cocktail or coffee, or take a dip in the river or pool. With open living spaces and thoughtful decor, this is your waterfront retreat.

Superhost
A spacious guest room features a king bed with crisp white linens and a neutral-colored bed skirt. Two bedside lamps illuminate the dark wood nightstands. A dresser and a chair are positioned near a window that allows natural light to brighten the room.
Apartment in Williamsburg
5 out of 5 average rating, 4 reviews

Beautiful 1BR at Williamsburg + Amenities

Built on the lush grounds of a former golf course, this quiet resort community is surrounded by the stunning landscape and historic spirit of Williamsburg. A great retreat any time of year, its central location also provides convenient access to explore all the area has to offer. • Guest checking in must be 21+ with valid ID. • Guest must have debit/credit card to put $250 refundable security deposit on hold at resort check-in. • Name on reservation must match photo ID at check-in.

Top guest favorite
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, 379 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.

Top guest favorite
The Gothic Revival-style cottage is showcased from its charming exterior, featuring large arched windows and a welcoming front porch. Two wooden chairs sit invitingly on the porch, complemented by seasonal decorations. Surrounding trees provide a sense of tranquility within the peaceful setting.
Cottage in Irvington
5 out of 5 average rating, 222 reviews

Peaceful Haven: nature & charming town

Do you want to get away from it all, change your surroundings and recharge yourself mentally and physically? Welcome to Peaceful Haven. Shops and restaurants of the lovely historic Village of Irvington are only a couple of minutes away. Hike just outside your door or in nearby parks, ride bikes around the meadows or to town, hang outside and listen to the birds, or just sink into the comfy couch to enjoy a movie on our large TV screen.

Top guest favorite
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, 147 reviews

Creekside Guesthouse - Dock and Pool on 10 acres

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 favorite
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.
Apartment in Williamsburg
4.85 out of 5 average rating, 169 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.

Superhost
The historic manor house is set on a landscaped property featuring manicured gardens and walkways. The two-story brick structure showcases symmetrical windows and a central door, framed by lush trees and colorful shrubs. The surrounding lawn is carefully maintained, enhancing the colonial architectural style.
Apartment in Williamsburg
4.94 out of 5 average rating, 34 reviews

2 Bedroom @ The Historic Powhatan Resort

Step back in time at The Historic Powhatan Resort, located on 256 acres of rolling woodland hills in historic Williamsburg, Virginia. • 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.

Top guest favorite
A row of well-maintained two-story condos is set against a bright blue sky. Neatly trimmed hedges and vibrant flowering shrubs enhance the front landscaping, providing a welcoming appearance. The buildings feature light-colored siding and gabled roofs, creating a charming residential atmosphere.
Apartment in Williamsburg
4.89 out of 5 average rating, 151 reviews

Historic Powhatan Resort- 2 bedroom condo!

Peacefully situated amid 256 acres of rolling woodland hills, and boasting all the character of a distinguished manor house, The Historic Powhatan Resort captures the essence of its Colonial surroundings. Originally built circa 1735, this restored manor house offers a serene getaway during any season.

Superhost
A serene lakeside view showcases a collection of three-story apartment buildings. The peaceful pond reflects the structures and greenery, while a gently bubbling fountain adds a touch of tranquility to the landscape.
Apartment in Williamsburg
4.93 out of 5 average rating, 14 reviews

Kingsgate Resort 3 Bedroom Lockoff

Located close to historic Williamsburg, the decor and atmosphere of Kingsgate Resort embodies the region's Colonial spirit. This peaceful resort is furnished in the style of the colonial period, yet it offers all the modern amenities and activities that will make your stay an enjoyable experience.

Guest favorite
The exterior of a historic brick building is shown, featuring a classic symmetrical design with multiple windows and a central entrance. A winding pathway leads through a landscaped yard, framed by trees and flower beds, suggesting a serene outdoor environment.
Apartment in Williamsburg
4.86 out of 5 average rating, 118 reviews

Best Resort/$$$ for Colonial Wburg & Busch Gardens

Our place is close to restaurants, supermarkets, dining and family-friendly activities. The resort is great for couples, solo adventurers, business travelers, families (with kids), and big groups. We are 10 minutes from Colonial Wburg & Jamestown and 20 minutes from Busch Gardens.

Superhost
A circular brick fire pit is surrounded by wooden chairs, providing an inviting gathering space. The outdoors is softly illuminated by ambient lighting, showcasing the cozy resort building in the background amidst lush greenery and a clear evening sky.
Apartment in Williamsburg
4.82 out of 5 average rating, 60 reviews

Cozy studio suite near Williamsburg historic area.

Built on the lush grounds of a former golf course, this quiet resort community is surrounded by the stunning landscape and historic spirit of Williamsburg. A great retreat any time of year, its central location also provides convenient access to explore all the area has to offer.

Popular amenities for Williamsburg rentals with a pool

When is the best time to visit Williamsburg?

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Quick stats about vacation rentals with a pool in Williamsburg

  • Total vacation rentals

    Explore 1,700 vacation rentals in Williamsburg

  • Nightly prices starting at

    Williamsburg vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 9,850 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,000 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    1,010 properties have a dedicated workspace

  • Wi-Fi availability

    1,700 of Williamsburg vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Williamsburg rentals

  • 4.7 Average rating

    Williamsburg stays receive an average rating of 4.7 out of 5 from guests

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