
Holiday 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.

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!

Millionaire $ Views No Xtra Charge! Hot Tub! POOL!
Welcome to The Cottage at Misti Cove, where you can experience the epitome of relaxation and tranquility. Immerse yourself in the serene ambiance of our cottage, aptly named for its simplicity, which belies the luxurious amenities that await you. At The Cottage at Misti Cove, we understand that the essence of a fulfilling vacation lies in the delicate balance between embracing the simple life and indulging in modern comforts. Here, you will discover a haven that seamlessly blends these elements

York River Vacation Home
This lovely, spacious waterfront home is located on the York River in Gloucester County Virginia. It is the perfect get away to enjoy the relaxing sounds and sights of nature. The views are spectacular! Keep an eye out for osprey and dolphins as you enjoy watching the sunrise and set over the water. There is plenty to do! Relax in the salt water pool overlooking the water, bring a pole & fish and crab right off of the private dock, or venture out on the kayaks. 16 ton boat lift, Jet ski lifts.

The Rosé Retreat: Pool-Screened Porch-RELAX
Escape to The Rosé Retreat for peace and relaxation. Enjoy a romantic getaway sipping wine on the screened porch, unwind by the refreshing pool, navigate the waterways by kayak, and stroll to great restaurants/shopping. Savor local oysters and explore nearby wineries. Bring the family for a memorable NNK adventure. The Rosé Retreat is a place to get away from it all. Enjoy a bottle (or more, we're not judging) of Rosé while you're here. Follow on IG:roseretreatva Irvington Occupancy Tax #500

Peaceful Retreat w/ Fire Pit & Spa Services
Country living at its best! Quiet...peaceful & very special place to relax, release, and rejuvenate. We are surrounded by beautiful wineries, which are all minutes away. Gorgeous views of nature and seasonal flowers. Separate from the main house, our guest suite offers awesome privacy & comfort. You will enjoy this very quiet, cozy, peaceful retreat. It is the perfect hideaway with the utmost charm. Board Certified Reflexologist on the premises is available for appointments. So AMAZING!

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?

The Barn at Pond Point - Riverfront Home
The Barn at Pond Point is perfectly situated on the Piankatank River, a salt water arm of the Chesapeake Bay. It shares 19 acres of wooded and waterfront property with the owner's main home. A unique space, Barn was converted from a working horse barn into a residence in the 1980's. With a quarter mile of private, sand beach and a large pool (May-Sept), the Barn is an ideal space for time with family and friends, swimming, hunting for prehistoric shark's teeth, or simply enjoying the view.

Magical wooded cottage pool +priv hottub walk2town
Set among the trees on 2 peaceful wooded acres, this cottage delights with gothic architecture, sun-filled rooms, and a bathroom for every bedroom. Relax in the hot tub under the stars, sip local wines, eat oysters. Take a sunset boat cruise or learn oystering and crabbing from a local waterman. Farm stands, markets, and sea-to-table local fare. Live life in an historic working water town with lots of personality. Close to Tides Inn, Kilmarnock, White Stone, Compass Entertainment.

Summer Escape • Dock, Pool, Firepits, & Kayaks
A waterfront summer retreat tucked into 10 secluded wooded acres above Bland Creek, perfect for long days and relaxed evenings - Screened porch with water views and cool creek breezes - A Pool is available for rent for private use (open Memorial Day–Labor Day) - Dock, kayaks, fishing, firepits, and direct water access -Outdooring dining options and family-friendly - Immaculately clean and thoughtfully stocked for a seamless stay - 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.

Pelican Place, Cozy Retreat | Pool | Walk to Tides
Unwind at this stylish apartment with view of Carters Creek and walking distance to the cutest little town and the iconic Tides Inn Resort. Take a refreshing dip in the pool, enjoy the charming outdoor shower, and star gaze under a blanket from the rooftop deck. Several outdoor spaces and large yard with whimsical touches. The perfect hideaway close to all the Northern Neck has to offer.

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

Wooded Wonderland Miniature Golf Hot tub Pool

Beautiful country house with 5 bedrooms 4.5 baths

Gorgeous Vacation House

Maddie's Place

Perfect Getaway!

Rappahannock Riverfront, Pool, Kayaks, Rose Garden

Serenity Farm Equestrian Retreat in Historic VA

Blue Oyster: Peaceful Getaway, Pool, Walk To Town
Condo rentals with a pool

Charming 2BR Colonial Condo at Wyndham Kingsgate

Charming 2BR Colonial Condo at Wyndham Kingsgate

Williamsburg 2bdr/2ba (6) near all the attractions

Powhatan Resort - 2 bdrm timeshare property

Wyndham Governor's Green, 2 BR Deluxe

Greensprings 4BDR for 12. Great location. $269 up

Kingsgate- 3 bedroom Williamsburg, VA

Relax in Style: 1BR Condo w/ Balcony at CW Governo
Other holiday rentals with a pool

Kingsgate 1 BedrooM

Cottage

The Blue Octopus~Private Pool~HotTub~Beach~FirePit

The Cottage @ Captain Genes - Secluded Waterfront

Waterfront home with heated pool available!

Waterfront Getaway w/ Pool, Firepit, Kayaks, Dock

Kingsgate Resort 3 Bedroom Lockoff

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 | $174 NZD | $183 NZD | $213 NZD | $222 NZD | $234 NZD | $244 NZD | $250 NZD | $223 NZD | $183 NZD | $199 NZD | $209 NZD | $171 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 1,690 holiday rentals in Williamsburg

Nightly prices starting at
Williamsburg holiday rentals start at $53 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
960 properties have a dedicated workspace

Wi-Fi availability
1,690 of Williamsburg holiday 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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- Chesapeake Bay
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- Greater Richmond Convention Center
- First Landing State Park
- Pocahontas State Park
- Jamestown Settlement
- Brown's Island
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- Norfolk Botanical Garden
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- Chrysler Museum of Art
- Science Museum of Virginia
- The Poe Museum
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- Nauticus
- Colonial Williamsburg's Merchants Square
- Altria Theater
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- Hampton University
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