Plan your trip

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

Check prices for these dates

Check prices for these dates, December 13 – 14, 2026

View in a map

Our top choices for Windsor hotels with a pool

1. Hampton Inn & Suites Windsor - Sonoma Wine Country

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

Location: Windsor
Guest rating: 9.2/10 (Wonderful, 1001 reviews)
Price: $122 nightly, $140 total, Nov 20 - Nov 21, Total with taxes and fees, for Our top choices for Windsor hotels with a pool

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

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

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

Location: Windsor
Guest rating: 9.2/10 (Wonderful, 1298 reviews)
Price: $99 nightly, $113 total, Dec 13 - Dec 14, Total with taxes and fees, for Our top choices for Windsor hotels with a pool

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

3. Holiday Inn Windsor Wine Country by IHG

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

Location: Windsor
Guest rating: 8.8/10 (Excellent, 1043 reviews)
Price: $115 nightly (Dive into a year-round swimming oasis at this hotel with a heated indoor pool and 24-hour fitness center.), $131 total, Dec 14 - Dec 15, Total with taxes and fees, for Our top choices for Windsor hotels with a pool

4. Hilton Garden Inn Sonoma County Airport

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

Location: Santa Rosa
Guest rating: 9.2/10 (Wonderful, 1000 reviews)
Price: $114 nightly (Dive into serene aquatic bliss at this hotel's indoor pool, open early till late daily.), $130 total, Nov 19 - Nov 20, Total with taxes and fees, for Our top choices for Windsor hotels with a pool

5. Hampton Inn & Suites Santa Rosa Sonoma Wine Country

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

Location: Santa Rosa
Guest rating: 9.4/10 (Exceptional, 637 reviews)
Price: $114 nightly, $132 total, Dec 5 - Dec 6, Total with taxes and fees, for Our top choices for Windsor hotels with a pool

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

6. Best Western Plus Wine Country Inn & Suites

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

Location: Santa Rosa
Guest rating: 8/10 (Very good, 1001 reviews)
Price: $115 nightly, $134 total, Dec 5 - Dec 6, Total with taxes and fees, for Our top choices for Windsor hotels with a pool

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

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

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

Location: Santa Rosa
Guest rating: 8.6/10 (Excellent, 2498 reviews)
Price: $97 nightly, $113 total, Dec 7 - Dec 8, Total with taxes and fees, for Our top choices for Windsor hotels with a pool

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

8. Dry Creek Inn MOD Collection by Sonesta

A multi-story hotel with a central archway, balconies, and a parking area.

Location: Healdsburg
Guest rating: 8.2/10 (Very good, 1003 reviews)
Price: $119 nightly, $138 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Windsor hotels with a pool

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

9. Holiday Inn Express Santa Rosa North by IHG

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

Location: Santa Rosa
Guest rating: 8.4/10 (Very good, 550 reviews)
Price: $103 nightly, $120 total, Dec 12 - Dec 13, Total with taxes and fees, for Our top choices for Windsor hotels with a pool

Dive into refreshing pool bliss at this Santa Rosa hotel with outdoor retreat and fitness perks.

10. The Lodge at Healdsburg, Tapestry Collection by Hilton

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

Location: Healdsburg
Guest rating: 9/10 (Wonderful, 576 reviews)
Price: $145 nightly, $168 total, Dec 2 - Dec 3, Total with taxes and fees, for Our top choices for Windsor hotels with a pool

Soak in relaxation at this Tuscan-style hotel, where the outdoor pool and 2 hot tubs create a serene retreat in Healdsburg.

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

View all properties

Choose what matters most at hotels with a pool in Windsor

Breakfast included

Hot tub

4 stars

5 stars

Spa

Top Windsor Hotel Reviews

Hampton Inn & Suites Windsor - Sonoma Wine Country

Address: 8937 Brooks Road South, Windsor, CA, 95492, US
Location: Windsor
Star rating: 2.5/5
Guest rating: 9.2/10 (1001 reviews)
Review: Could use a cabinet in the bathroom. There was nowhere to put toiletries down while using the sink etc. Front seat was excellent. overall, great place to stay!, by John, April 22, 2024, rated 10/10 Excellent

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Address: 8865 Conde Lane, Windsor, CA, 95492, US
Location: Windsor
Star rating: 2.5/5
Guest rating: 9.2/10 (1298 reviews)
Review: Good breakfast, by john, February 20, 2025, rated 10/10 Excellent

Hilton Garden Inn Sonoma County Airport

Address: 417 Aviation Blvd, Santa Rosa, CA, 95403, US
Location: Santa Rosa
Star rating: 3/5
Guest rating: 9.2/10 (1000 reviews)
Review: 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., by Richard, March 27, 2018, rated 10/10 Excellent

Hampton Inn & Suites Santa Rosa Sonoma Wine Country

Address: 3815 AIRWAY DR, Santa Rosa, CA, 95403, US
Location: Santa Rosa
Star rating: 2.5/5
Guest rating: 9.4/10 (637 reviews)
Review: Homewood is perfect for family. The property is clean, spacious, comfortable. It has laundry for client use, pool and gym. Also, the reservation includes breakfast which is great. The hotel is 7-9 minutes away from downtown of Santa Rosa. Hotel is on its own, have to drive around to go to restaurants but fortunately nearby places are 7-10 minutes drive only., by KATRINA, June 23, 2024, rated 10/10 Excellent

Holiday Inn Windsor Wine Country by IHG

Address: 8755 Old Redwood Hwy, Windsor, CA, 95492, US
Location: Windsor
Star rating: 3/5
Guest rating: 8.8/10 (1043 reviews)
Review: Will stay again, by Gek Hong, July 6, 2025, rated 10/10 Excellent

Cottages on River Road

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

Location: Guerneville
Review: Great place, friendly staff. Comfortable accommodations with a nice breakfast. Pool is wonderful during the summer months. There are 2 great places to eat across the street right by the river-Farmhand & Stumptown brewery-very convenient. Also convenient to Armstrong Woods. Will be back!, by Julie, January 21, 2025, rated 10/10 Excellent

Hotel Trio Healdsburg

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

Location: Healdsburg
Review: Excellent & helpful staff. Great downtown area., by Allison, April 9, 2025, rated 10/10 Excellent

Vinarosa Resort & Spa

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

Location: Santa Rosa
Review: 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..., by Sarah, July 24, 2017, rated 10/10 Excellent

The Lodge at Healdsburg, Tapestry Collection by Hilton

Address: 1261 Grove St, Healdsburg, CA, 95448, US
Location: Healdsburg
Star rating: 4/5
Guest rating: 9/10 (576 reviews)
Review: Everything was awesome except for the sauna and stem room which either did not work or work very well. Also, why charge for parking? Not a big fan of that. Other thank that amazing., by Andrew, April 5, 2023, rated 10/10 Excellent

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

Address: 3421 Cleveland Ave, Santa Rosa, CA, 95403, US
Location: Santa Rosa
Star rating: 3/5
Guest rating: 8.6/10 (2498 reviews)
Review: The only negative was that yard maintenance was happening at 0700 in the morning with blowers. But all else was perfect., by angela, March 25, 2025, rated 10/10 Excellent

Camellia Inn

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

Location: Healdsburg
Review: What we liked most was the staff was very friendly. The parking and pool area not inviting at all. Nothing was kept crisp and clean.The surroundings of the parking lot needs more coverage from the neighbors., by Kirk, May 19, 2025, rated 10/10 Excellent

Harmon Guest House

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

Location: Healdsburg
Review: Absolutely wonderful stay, maybe my favorite hotel in America. Very clean, very well designed, elegant but not ornate. Loved it., by Kevin, June 17, 2025, rated 10/10 Excellent

The Inn on Pine

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

Location: Calistoga
Review: We could walk the 2 blocks for shopping and dinner. The owners were great, loved breakfast outside each day, We stayed just 2 night so we had a smaller room. Next time we will stay longer and opt for something larger. We also had a massage one day, Nina and Salvatore were both excellent., by Dana, March 25, 2017, rated 10/10 Excellent

Holiday Inn Express Santa Rosa North by IHG

Address: 2632 Cleveland Ave, Santa Rosa, CA, 95403, US
Location: Santa Rosa
Star rating: 2.5/5
Guest rating: 8.4/10 (550 reviews)
Review: This is my go to Hotel when in Santa Rosa. Clean, friendly and comfortable beds to sleep. Very convenient location to get out to Calistoga or the West County and close to 101., by Nicholas, November 28, 2024, rated 10/10 Excellent

Grape Leaf Inn

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

Location: Healdsburg
Review: We are return visitors to The Grape Leaf Inn. Good location, beautiful Inn, outstanding attention to service by the Innkeeper. Delicious breakfasts. Loved the Speak Easy and mixologist. Would return again., by Hedda, May 12, 2015, rated 10/10 Excellent

Best Western Plus Wine Country Inn & Suites

Address: 870 Hopper Ave, Santa Rosa, CA, 95403, US
Location: Santa Rosa
Star rating: 2.5/5
Guest rating: 8/10 (1001 reviews)
Review: As soon as we walked in we were greeted with friendliness and polite staff. Right away offered cookies, coffee and water. Rooms clean. Excellent location. Conveniently walking distance to food and shopping. Would definitely stay again when in area., by dianna, March 2, 2025, rated 10/10 Excellent

Geyserville Inn

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

Location: Geyserville
Review: Great hotel to stay at while we dined at Cyrus. Cute and great price. Wish they had breakfast on Friday morning. Cassidy was very helpful- she went out of her way to accommodate us on the 1st floor., by Sharon, January 29, 2023, rated 10/10 Excellent

Appellation Healdsburg

A swimming pool with lounge chairs and umbrellas, surrounded by a landscaped area and buildings.

Location: Healdsburg
Review: Beautiful property! The room was beautiful and spacious. The location was great, a few minutes from the town so we got to enjoy that area as well. I really recommend this hotel., by Alexis, March 30, 2026, rated 10/10 Excellent

H2Hotel

A swimming pool area with lounge chairs, a glass wall with plants, and a modern interior design.

Location: Healdsburg
Review: Loved the location, very nice, quiet and modern and spacious rooms. Easy 3 minute walk to the town square with nice boutiques and wonderful restaurants. The continental breakfast should have more selection options for breads. At 8:30am they only had one type of small cinnamon pastry, no toasts or croissants. There was yogurt, cereal and fruit but some fresh baked goods, croissants, breads, bagels and jams would be nice and are served at most places that offer continental breakfast., by Anonymous traveler, January 27, 2022, rated 10/10 Excellent

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.

Explore a world of travel with Expedia

Lodging