A park with a statue of a figure on horseback, surrounded by leafless trees and a clear sky.

Find Hotels with a Pool in Windsor, CA

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November 2026

December 2026

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Our top choices for Windsor hotels with a pool

A swimming pool with a fence, lounge chairs, and a building with columns.

1. Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Windsor

Refresh poolside with panoramic views, hot tub delights, and a sauna that elevates relaxation at this wine country retreat.

$105 nightly

Dec 6 - Dec 7

Total with taxes and fees

A pool area with lounge chairs and umbrellas, surrounded by a building with multiple windows and balconies.

2. Hampton Inn & Suites Windsor - Sonoma Wine Country

Windsor

Dive into aquatic relaxation at this modern hotel featuring a heated outdoor pool and hot tub surrounded by serene lounging areas.

$122 nightly

Nov 20 - Nov 21

Total with taxes and fees

A swimming pool area with lounge chairs and a no diving sign.

3. Holiday Inn Windsor Wine Country by IHG

Windsor

Dive into a year-round swimming oasis at this hotel with a heated indoor pool and 24-hour fitness center.

$118 nightly

Nov 15 - Nov 16

Total with taxes and fees

A house with a swimming pool, outdoor furniture, and a well-maintained garden.

4. Eastside Eden - Pool, Hot Tub and Tastings Included

Healdsburg

$1,157 nightly

Nov 12 - Nov 13

Total with taxes and fees

A swimming pool with a clear blue sky, surrounded by multi-story buildings with balconies.

5. Tuscan by Onalani 3BR Year-round pools & hot tubs

Windsor

$1,654 nightly

Nov 27 - Nov 28

Total with taxes and fees

A swimming pool with lounge chairs and a sunshade, surrounded by large windows.

6. Hilton Garden Inn Sonoma County Airport

Santa Rosa

Dive into serene aquatic bliss at this hotel's indoor pool, open early till late daily.

$114 nightly

Nov 21 - Nov 22

Total with taxes and fees

A Hampton Inn & Suites with a pool area, outdoor seating, and a clear blue sky.

7. Hampton Inn & Suites Santa Rosa Sonoma Wine Country

Santa Rosa

Float in tranquil waters at this wine country hotel, boasting a sun-drenched outdoor pool and a state-of-the-art gym.

$114 nightly

Dec 5 - Dec 6

Total with taxes and fees

A swimming pool with lounge chairs and umbrellas, surrounded by a fence and greenery.

8. Best Western Plus Wine Country Inn & Suites

Santa Rosa

Sparkling outdoor pool retreat with comfortable loungers offers refreshing relaxation in the heart of wine country.

$115 nightly

Dec 5 - Dec 6

Total with taxes and fees

A hotel pool area with a hot tub, lounge chairs, and a building in the background.

9. The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

Santa Rosa

Splash into serene Santa Rosa with a sun-soaked pool experience and poolside cocktails.

$97 nightly

Dec 7 - Dec 8

Total with taxes and fees

A swimming pool with lounge chairs and a covered seating area, surrounded by a white building with arches and a flagpole.

10. Dry Creek Inn MOD Collection by Sonesta

Healdsburg

Dive into sun-soaked relaxation with an outdoor pool, bicycles, and vineyard tours nearby.

$119 nightly

Nov 15 - Nov 16

Total with taxes and fees

View all properties

Choose what matters most at hotels with a pool in Windsor

Breakfast included

Hot tub

Top Windsor Hotel Reviews

Hampton Inn & Suites Windsor - Sonoma Wine Country

Windsor

10/10 Excellent

John

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Windsor

10/10 Excellent

john

Hilton Garden Inn Sonoma County Airport

Santa Rosa

10/10 Excellent

The hotel and the room was very nice. The front desk staff was also very nice. But beware of the slippery bathtubs. They have a rubber mat that you roll out yourself, but it's very small. My husband fell out of the bath tub because of a mis-step. We reported it to the front desk and filed a report just in case. I think he's fine, but remember to step on the rubber mat and not anywhere else in the tub.

Richard

Hampton Inn & Suites Santa Rosa Sonoma Wine Country

Santa Rosa

10/10 Excellent

KATRINA

A swimming pool with a curved edge, surrounded by a deck with lounge chairs and a covered seating area.

Cottages on River Road

Guerneville

10/10 Excellent

Julie

A swimming pool with lounge chairs, a pergola, and a gazebo.

The Lodge at Healdsburg, Tapestry Collection by Hilton

Healdsburg

10/10 Excellent

Andrew

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

Santa Rosa

10/10 Excellent

angela

A resort with a large pool surrounded by lounge chairs and umbrellas, set in a landscaped area with buildings in the background.

Vinarosa Resort & Spa

Santa Rosa

10/10 Excellent

The hotel grounds were lovely, and the room was comfortable and spacious, but the overall service, while friendly, is not as good as it should be for the price. The front desk completely neglected to tell us about any of the "extras", like the free wine tastings at Ferrari-Carrano vineyards (value of $35 per person), the complimentary daily wine tasting at the hotel, and the corkage fee waiver at John Ashe for bottles purchased at Ferrari-Carrano ($25 value). None of these perks are mentioned on...

Sarah

A pool area with lounge chairs and a view of mountains.

The Inn on Pine

Calistoga

10/10 Excellent

Dana

A poolside area with lounge chairs, a flamingo float, and a wooden fence in the background.

Camellia Inn

Healdsburg

10/10 Excellent

Kirk

Dry Creek Inn MOD Collection by Sonesta

Healdsburg

10/10 Excellent

George

A poolside area with lounge chairs, a wooden pergola, and a view of a swimming pool.

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

Santa Rosa

10/10 Excellent

Timm

Best Western Plus Wine Country Inn & Suites

Santa Rosa

10/10 Excellent

dianna

A person floating in a pool with a colorful unicorn float, a building with balconies, and a clear blue sky.

Geyserville Inn

Geyserville

10/10 Excellent

Sharon

A swimming pool with a clear view of the poolside area, including a lounge chair and a metal pool ladder.

Hyatt Regency Sonoma Wine Country

Historic Railroad Square

10/10 Excellent

Bruce

A swimming pool with lounge chairs and umbrellas, surrounded by a multi-story building with balconies.

Holiday Inn Express Santa Rosa North by IHG

Santa Rosa

10/10 Excellent

Nicholas

A poolside area with a tiled deck, a pool with a depth marker, and outdoor seating with chairs and tables.

Harmon Guest House

Healdsburg

10/10 Excellent

Kevin

A swimming pool with a metal safety rail, two red lounge chairs, and a wooden fence.

Grape Leaf Inn

Healdsburg

10/10 Excellent

Hedda

Frequently Asked Questions

How much does a hotel with outdoor pool in Windsor cost?

Enjoy staying in a hotel in Windsor with an outdoor pool. You can find a great deal from $112 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.

Are there hotels in Windsor that have private outdoor pools?

Eastside Eden | Wine Tastings Included is an exceptional choice for those seeking a hotel in Windsor with a private outdoor pool. Rated an impressive 9.0 by guests, this hotel offers a serene retreat where families can enjoy the stunning mountain views and relax in the comfort of their own private pool.

Beyond the inviting pool, Eastside Eden also provides a well-equipped kitchen, superb for preparing meals together, making it convenient for families who prefer dining in. For those eager to explore, the hotel is located near exciting outdoor activities like mountain climbing and biking, ensuring that adventure is just moments away.

Is it cheaper to book flights and a Windsor hotel with a pool as a package?

Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it’s wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.

Can I cancel my hotel reservation on Expedia?

Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Windsor for you.

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