
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!

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.

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.

Comfortable 1BR Retreat in Williamsburg
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.

Relax in Style: 1BR Condo w/ Balcony at Wyndham GG
Welcome to our beautiful 1BR Condo close to Historic Williamsburg! 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, we offer easy access to some of Williamsburg's most popular destinations.

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.

Waterfront Escape • Pool, Dock & Creek View
A peaceful waterfront retreat tucked into 10 wooded acres above Bland Creek, perfect for long summer days and relaxed evenings. - Private screened-in porch with cooling creek breezes - Pool days, firepits under the stars, and quiet moments outdoors - Kayaks, a floating dock, fishing, and nature right outside your door - Immaculately clean and thoughtfully stocked for a stress-free stay - Quiet setting just minutes from downtown Gloucester

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.

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. Sumptuous, spacious accommodations offer a private balcony, loft and hot tub. Originally built circa 1735, this restored manor house offers a serene getaway during any season.

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.

1 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.

Cozy 2BR Condo in Williamsburg
Welcome to your getaway in Williamsburg, Virginia! Escape to our luxurious condo located in Kingmill resort on a pristine golf course in the heart of historic Williamsburg, Virginia. This beautifully furnished 2-bedroom, 2-bathroom retreat offers the perfect blend of relaxation and adventure for families and vacationers alike.
Popular amenities for Williamsburg rentals with a pool
House rentals with a pool

Wooded Wonderland Miniature Golf Hot tub Pool

York River Vacation Home

Gorgeous Vacation House

Blue Heron WaterSide

Perfect Getaway!

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

Williamsburg Plantation ThanksGiving Large Condo 2

Apartment Resort Williamsburg 2bdrm

Patrick Henry Square Resort | 2-bedroom Suite

Charming 3BR Colonial Condo at Wyndham Kingsgate

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

Cozy condo in the heart of shopping and dining!!!

Upscale condo with Golf Course views

Patriots Place 2 Bedroom
Other holiday rentals with a pool

2 Bedroom Greensprings Vacation Resort (Sleeps 6)

Suitable 1BR Near Top Attractions!

Dreamy Serenity*The Historic Powhatan Resort 1B #3

Spacious 4 BD Suite near Colonial Williamsburg

2 Bedroom(4 beds) @ The Historic Powhatan Resort

1 Bedroom Suite at Historic Resort+Amenities!

Kingsgate 1 bedroom

4 Bedroom at The Historic Powhatan Resort
When is the best time to visit Williamsburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $125 SGD | $132 SGD | $153 SGD | $160 SGD | $168 SGD | $176 SGD | $180 SGD | $161 SGD | $132 SGD | $143 SGD | $151 SGD | $123 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 $38 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
- Greater Richmond Convention Center
- Water Country USA
- First Landing State Park
- Pocahontas State Park
- Buckroe Beach
- Jamestown Settlement
- Brown's Island
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
- Libby Hill Park
- Chrysler Museum of Art
- Science Museum of Virginia
- The Poe Museum
- Hollywood Cemetery
- Virginia Living History Museum
- Old Dominion University
- Colonial Williamsburg's Merchants Square
- Virginia Holocaust Museum
- Altria Theater
- Virginia Zoological Park




