
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 2bd2ba Condo on Golf Course 9th Fairway!
This beautiful, 2B2Ba condo is 1400 sq.ft. in the exclusive Kingsmill neighborhood. This 1st floor unit has two master suites w/ king beds. One features a luxurious bathroom w/ a walk-in shower & dual shower heads, the other has a shower/tub combo as well as a private patio, stepping out onto the 9th Fairway. The open-concept living space has dining for 6, a queen sleeper sofa, a fully stocked kitchen, and an additional private patio. Golf course views from anywhere in the main living space!

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

Blue Heron WaterSide
Blue Heron Waterside awaits you...Private Hot Tub and Pool!Waterfront and Pier- Kayaks included! This retreat is set up with you in mind for a special get away.Relax.Enjoy being together plus space to have quiet time. Sunroom, spacious deck, private Pool, Hot tub and Pier create a waterfront living experience. Grab a book, go for a swim or lounge by the pool. Explore the water with a variety of Kayaks plus a Stand Up Paddle Board.Great location to fish and crab from the pier. Are you ready?

Kingsgate 2BR w/ Kitchen
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. 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 resort.

Wtrfrnt aptmnt w/pool/dock on private farm
Escape to this serene waterfront estate, offering a private, fully-equipped studio apartment with stunning cove views from every window. 14 acres of peaceful grounds—saltwater pool, fish from the private dock, or kayak right from the shore. 10 minutes from Mathews and Gloucester’s farm-to-table dining, and steps from the Peninsula's famed art scene with galleries, antiques, and local crafts. Plus, we're right on the doorstep of the Historic Triangle—Williamsburg, Yorktown, and Jamestown.

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.

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.

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.

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.

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.

1BR Suite in Williamsburg @ All Inclusive 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.

1 Bedroom Suite at Historic Resort+Amenities!
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.
Popular amenities for Williamsburg rentals with a pool
House rentals with a pool

York River Vacation Home

Chesapeake Bay Retreat Waterfront Indoor Pool

Gorgeous Vacation House

The Rosé Retreat: Fireplace-Screened Porch-RELAX

Magical wooded cottage pool +priv hottub walk2town

Waterfront Cottage Getaway Views/Kayaks/Fire Pit

𓂃Tidal Creek Retreat: Near CNU, JLab and Busch𓂃

4BD home w/ game room & pool near Langley & PTC!
Condo rentals with a pool

Wyndham Kingsgate (2 BD)

Charming 3BR Colonial Condo at Wyndham Kingsgate

Great family vacation resort condo. Sleeps 12.

3BDR 2 bath, Sleeps up to 8 Guests

Historic Powhatan resort 2 bdrm

Wyndham Patriots' Place one bedroom

Wyndham Governor's Green (3 Bed Deluxe)

Cozy 1 Bedroom Condo at Kingsgate Wyndham Resort
Other holiday rentals with a pool

Kingsgate one bedroom

Patriots Place studio

Historic Powhatan Resort- 2 bedroom condo!

Spacious 4 BD Suite near Colonial Williamsburg

Historic Charm & Modern Comfort at Hilton Powhatan

Historic Powhatan Resort- 2 bedroom condo!

The Historic Powhatan, 2br suite, Saturday check-i

Club Wyndham Kingsgate One-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 | $173 NZD | $181 NZD | $211 NZD | $220 NZD | $232 NZD | $242 NZD | $248 NZD | $222 NZD | $181 NZD | $206 NZD | $223 NZD | $195 NZD |
| 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 1,700 holiday rentals in Williamsburg

Nightly prices starting at
Williamsburg holiday rentals start at $52 NZD per night before taxes and fees

Verified guest reviews
Over 9,850 verified reviews to help you choose

Family-friendly holiday rentals
1,000 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
1,010 properties have a dedicated workspace

Wi-Fi availability
1,700 of Williamsburg holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Buckroe Beach
- Carytown
- Water Country USA
- First Landing State Park
- Pocahontas State Park
- Haven Beach
- Buckroe Beach
- Brown's Island
- Jamestown Settlement
- Grandview Beach
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