Title: Book the Best Hotels with POOL in Healdsburg in 2025 | Expedia.ca [Hotels in Healdsburg](https://expedia.ca/Healdsburg-Hotels.d8322.Travel-Guide-Hotels)[Vacation Rentals in Healdsburg](https://expedia.ca/Healdsburg-Vacation-Rentals.d8322.Travel-Guide-VacationRentals)[Flights to Healdsburg](https://expedia.ca/Cheap-Flights-To-Healdsburg.d8322.Travel-Guide-Flights)[Healdsburg Car Rentals](https://expedia.ca/Car-Rentals-In-Healdsburg.d8322.Car-Rental-Guide)[Healdsburg Vacation Packages](https://expedia.ca/Healdsburg.d8322.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/215000/215993-Healdsburg-Sc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Healdsburg, CA from CA $148 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Healdsburg Hotels with a Pool Tonight [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2025-10-11&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2025-10-12&endDate=2025-10-13&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Healdsburg Hotels with a Pool ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273394/e43ebe8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273394/6e9c3a9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273394/739126e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273394/965e1808.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express® Windsor Sonoma Wine Country by IHG Windsor 9.2/10 Wonderful (1202) "perfect for us while passing through" CA $155 CA $177 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Windsor-Hotels-Holiday-Inn-Express-Windsor-Sonoma-Wine-Country.h1273394.Hotel-Information) ![Deluxe Queen Room | View from room](https://images.trvl-media.com/lodging/2000000/1250000/1249600/1249559/5091b1c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1250000/1249600/1249559/7965154c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/2000000/1250000/1249600/1249559/6bcd9a1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, pool views ](https://images.trvl-media.com/lodging/2000000/1250000/1249600/1249559/ad641ef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Geyserville Inn Geyserville 9.2/10 Wonderful (1000) "Great spot in Geyserville!" CA $183 CA $228 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Geyserville-Hotels-Geyserville-Inn.h1249559.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/900000/899000/898926/504341e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/900000/899000/898926/aace526e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/900000/899000/898926/43e5a0f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/900000/899000/898926/828e3c2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottages on River Road Guerneville 9.6/10 Exceptional (1007) "Loved this charming property!" CA $150 CA $180 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Guerneville-Hotels-Cottages-On-River-Road.h898926.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/24000000/23260000/23251300/23251292/d549cb76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/24000000/23260000/23251300/23251292/87244c80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/24000000/23260000/23251300/23251292/53dcce2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/24000000/23260000/23251300/23251292/96f5eb3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Trio Healdsburg Healdsburg 9.4/10 Exceptional (845) "Staff was very welcoming!" CA $226 CA $291 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Healdsburg-Hotels-Hotel-Trio-Healdsburg.h23251292.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/14000000/13240000/13235900/13235845/c52eb6f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/14000000/13240000/13235900/13235845/48ef5836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/14000000/13240000/13235900/13235845/4ee5159b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/14000000/13240000/13235900/13235845/c47d7bff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Windsor Wine Country by IHG Windsor 9.0/10 Wonderful (1012) "Good location, just off the highway" CA $139 CA $158 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Windsor-Hotels-Holiday-Inn-Windsor-Wine-Country.h13235845.Hotel-Information) ![Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/84000000/83700000/83691500/83691429/6b333fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/84000000/83700000/83691500/83691429/a3467580.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/84000000/83700000/83691500/83691429/540cf294.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83700000/83691500/83691429/81a03092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lodge at Healdsburg, Tapestry Collection by Hilton Healdsburg 9.0/10 Wonderful (356) "A wonderful property! Staff friendly, food options. Coffee options, walkable to the town center. Will visit again! " CA $237 CA $275 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Healdsburg-Hotels-The-Lodge-At-Healdsburg.h83691429.Hotel-Information) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/920000/919800/919721/3fddbec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/920000/919800/919721/7e067917.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/920000/919800/919721/1d6a8d35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/919800/919721/5872ccb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel Santa Rosa 8.4/10 Very good (1986) "Nice and family place to stay" CA $128 CA $148 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Santa-Rosa-Hotels-The-Sandman.h919721.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/119000000/118740000/118739000/118738917/406a3e2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed (Vaulted)](https://images.trvl-media.com/lodging/119000000/118740000/118739000/118738917/37e554c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/119000000/118740000/118739000/118738917/9630f2c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118740000/118739000/118738917/a9e929f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Appellation Healdsburg Healdsburg 9.8/10 Exceptional (8) "This hotel is brand now and on the northern end of Healdsburg and we were amongst the first guests. Absolutely loved it - especially the restaurants and the pools. Staff was lovely and accommodating and we cannot wait to return." CA $616 CA $799 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Healdsburg-Hotels-Appellation-Healdsburg.h118738917.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1870000/1865900/1865821/6b56192d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1870000/1865900/1865821/c1fa54a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1870000/1865900/1865821/96c44de3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/2000000/1870000/1865900/1865821/dc1b4807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Sonoma County Airport Santa Rosa 9.2/10 Wonderful (981) "Nice hotel with awesome friendly staff. " CA $160 CA $182 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Santa-Rosa-Hotels-Hilton-Garden-Inn-Sonoma-County-Airport.h1865821.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19400/19399/992810dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/19400/19399/2ee3c403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Fireplace (with Sofabed) | Living area](https://images.trvl-media.com/lodging/1000000/20000/19400/19399/f85bb490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/20000/19400/19399/3671ac65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Dry Creek Inn Healdsburg 8.0/10 Very good (1006) "Great place to stay" CA $195 CA $227 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Healdsburg-Hotels-Best-Western-Dry-Creek-Inn.h19399.Hotel-Information) 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](https://expedia.ca/Hotel-Search?startDate=2025-10-25&endDate=2025-10-26®ionId=8322&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Healdsburg Hotel Reviews ![Best Western Dry Creek Inn](//images.trvl-media.com/lodging/1000000/20000/19400/19399/f85bb490_y.jpg) ### Best Western Dry Creek Inn 10/10 Excellent "Great place to stay" [](https://expedia.ca/Healdsburg-Hotels-Best-Western-Dry-Creek-Inn.h19399.Hotel-Information) ![Hotel Healdsburg](//images.trvl-media.com/lodging/1000000/790000/786900/786805/9d93bedd_y.jpg) ### Hotel Healdsburg 10/10 Excellent "Lovely hotel in the heart of Healdsburg. Wonderful stay. " [](https://expedia.ca/Healdsburg-Hotels-Hotel-Healdsburg.h786805.Hotel-Information) ![Fairview Inn and Suites](//images.trvl-media.com/lodging/2000000/1120000/1111500/1111427/55aee5ca_y.jpg) ### Fairview Inn and Suites 10/10 Excellent "Very Clean and Modern. Would definitely stay again." [](https://expedia.ca/Healdsburg-Hotels-Fairview-Inn-And-Suites.h1111427.Hotel-Information) ![H2Hotel](//images.trvl-media.com/lodging/4000000/3620000/3618400/3618334/92a67a3e_y.jpg) ### H2Hotel 10/10 Excellent "I enjoyed the ambiance, friendliness and cleanliness. Everyone seemed to be happy" [](https://expedia.ca/Healdsburg-Hotels-H2hotel.h3618334.Hotel-Information) ![The Madrona](//images.trvl-media.com/lodging/1000000/460000/451700/451693/ac03bc94_y.jpg) ### The Madrona 10/10 Excellent "My stay at The Madrona was nothing short of beautiful, relaxing and calming. The property itself is stunning, quiet and soothing and my room was more than I could have asked for. I was only staying for one night so I had dinner there and it was delicious. I wish I could have stayed longer. The staff is friendly and welcoming and I will be returning as soon as I possibly can. It’s a perfect place to relax. " [](https://expedia.ca/Healdsburg-Hotels-The-Madrona.h451693.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Healdsburg? > [Hotel Trio Healdsburg](https://www.expedia.ca/Healdsburg-Hotels-Hotel-Trio-Healdsburg.h23251292.Hotel-Information): Features a snack bar/deli, an outdoor pool, and full. [Fairview Inn and Suites](https://www.expedia.ca/Healdsburg-Hotels-Fairview-Inn-And-Suites.h1111427.Hotel-Information): Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. [Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!](https://www.expedia.ca/Healdsburg-Hotels-Spectacular-Healdsburg-Manor-4BR45BA.h96823655.Hotel-Information): Provides complimentary wireless internet access, a pool, and kitchens. [Healdsburg, sleeps 10, pool, hot tub, gardens, BBQ, Vineyard Views](https://www.expedia.ca/Healdsburg-Hotels-Healdsburg.h93235284.Hotel-Information): Features kitchens, a pool, and a hot tub. ### What is there to see and do in Healdsburg? > Spend some time experiencing the great outdoors at Russian River and Healdsburg Ridge Open Space Preserve. During your stay, check out sights such as Healdsburg Plaza, Jordan Vineyard & Winery, and SingleThread Farm at Dry Creek. Healdsburg appeals to visitors with its beautiful river views, selection of wineries, and array of dining options. ### When is the best time to book a hotel with a pool in Healdsburg? > You may want to consider a place to stay with an outdoor swimming pool if you're planning to visit Healdsburg in the hottest months of July, August, or September when the average temperature is 69°F. 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[Boutique Hotels in Geyserville](https://www.expedia.ca/Geyserville-Hotels-Boutique-Hotel.0-0-d182974-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Geyserville](https://www.expedia.ca/Geyserville-Hotels-Cheap-Hotels.0-0-d182974-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Geyserville](https://www.expedia.ca/Geyserville-Hotels-Luxury-Hotel.0-0-d182974-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Geyserville](https://www.expedia.ca/Geyserville-Hotels-Pet-Friendly-Hotel.0-0-d182974-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Geyserville](https://www.expedia.ca/Geyserville-Hotels-Spa-Hotel.0-0-d182974-tSpaHotel.Travel-Guide-Filter-Hotels) - [Winery Hotels in Geyserville](https://www.expedia.ca/Geyserville-Hotels-Winery-Hotel.0-0-d182974-tWineryHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Napa](https://www.expedia.ca/Napa-Hotels-Business-Hotel.0-0-d6141-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Napa](https://www.expedia.ca/Napa-Hotels-Hotels-With-Bar.0-0-d6141-tHotelswithBar.Travel-Guide-Filter-Hotels) - 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