
Holiday rentals with a pool in Williamsburg
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Williamsburg
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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!

Creekside, Pool, Dock & Firepits, Elevated Porch
- Waterfront retreat on 10 wooded acres above Bland Creek - Immaculately clean, frequently described as spotless and pristine - Private screened-in porch with peaceful creek and marsh views - Kayaks, a floating dock, fishing, firepits, and nature right outside your door - Well-stocked kitchen plus full-size washer and dryer - Thoughtful hosting with local recommendations, guidebook, and fresh cookies - Peaceful setting just minutes from downtown Gloucester and 45 minutes from Williamsburg

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.

Charming 1BR Colonial Condo at Wyndham 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.

Suitable 1BR Near Top Attractions!
Furnished in the Colonial style, this resort offers all the modern amenities and activities you could want. Surrounded by the area's top attractions and historic landmarks, there's plenty to explore, ensuring that your getaway is one to remember. • 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. . Resort Fee at $7 per night. • Name on reservation must match photo ID at check-in.

Chic Urban Living: 1BR in Kingsgate!
Furnished in the Colonial style, this resort offers all the modern amenities and activities you could want. Surrounded by the area's top attractions and historic landmarks, there's plenty to explore, ensuring that your getaway is one to remember. • 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. . Resort Fee at $7 per night. • Name on reservation must match photo ID at check-in.

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.

Wyndham Governor's Green, 3 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.

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.

Governor’s Green 2 BR DLX
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. Just three miles north of historic Williamsburg, Club Wyndham Governor's Green offers easy access to some of Williamsburg's most popular destinations.

*Historic Powhatan Resort- 2 bedroom
Step back in time at The Historic Powhatan Resort, located on 256 acres of rolling woodland hills in historic Williamsburg, Virginia. The resort features a distinguished manor house that was originally built in 1735 and captures the true essence of its Colonial surroundings. Discover the nation’s history at one of Williamsburg’s history museums, monuments or battlefields, and immerse yourself in the city’s Colonial spirit.

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.
Popular amenities for Williamsburg rentals with a pool
House rentals with a pool

York River Vacation Home

Chesapeake Bay Retreat Waterfront Indoor Pool

Our Home Away from Home

Gorgeous Vacation House

Blue Heron WaterSide

The Rosé Retreat: Fireplace-Screened Porch-RELAX

Magical wooded cottage pool +priv hottub walk2town

𓂃Tidal Creek Retreat: Near CNU, JLab and Busch𓂃
Apartment rentals with a pool

Charming 3BR Colonial Condo at Wyndham Kingsgate

Great value! Popular Powhatan Resort 2BDR

Marriott Manor Club Luxury 1BD villa sleeps 4

Charming 1BR Colonial Condo at Wyndham Kingsgate

Wyndham Patriots' Place one bedroom

1br Colonial in Williamsburg -Fun by Busch Gardens

Colonial Williamsburg Spacious 4 Bedroom Suite!

Wyndham Kingsgate (3 BD LO)
Other holiday rentals with a pool

Kingsgate one bedroom

1BR Suite in Williamsburg @ All Inclusive Resort!

Spacious 4 BD Suite near Colonial Williamsburg

Historic Charm & Modern Comfort at Hilton Powhatan

Historic Powhatan Resort- 2 bedroom condo!

3 Bedroom Suite in Historic Williamsburg!

Kingsgate 2BR w/ Kitchen

Historic Powhatan Resort- 2 bedroom condo!
When is the best time to visit Williamsburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $128 SGD | $134 SGD | $156 SGD | $162 SGD | $171 SGD | $179 SGD | $183 SGD | $164 SGD | $134 SGD | $152 SGD | $165 SGD | $144 SGD |
| Avg. temp | 5°C | 6°C | 9°C | 15°C | 19°C | 24°C | 26°C | 25°C | 22°C | 16°C | 11°C | 7°C |
Quick stats about holiday rentals with a pool in Williamsburg

Total holiday rentals
Explore 1,690 holiday rentals in Williamsburg

Nightly prices starting at
Williamsburg holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 10,640 verified reviews to help you choose

Family-friendly holiday rentals
1,000 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
960 properties have a dedicated workspace

Wifi availability
1,690 of Williamsburg holiday rentals include wifi 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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- Chesapeake Bay
- Busch Gardens Williamsburg
- Carytown
- Water Country USA
- First Landing State Park
- Pocahontas State Park
- Buckroe Beach
- Jamestown Settlement
- Brown's Island
- Outlook Beach
- Norfolk Botanical Garden
- Cape Charles Beachfront
- Chrysler Museum of Art
- Libby Hill Park
- The Poe Museum
- Science Museum of Virginia
- Hollywood Cemetery
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- Nauticus
- Old Dominion University
- Greater Richmond Convention Center
- First Landing Beach
- Colonial Williamsburg's Merchants Square
- Hampton University




