Title: Book the Best Hotels with POOL in Healdsburg in 2026 | 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) ![Dry Creek Vineyard showing signage](https://images.trvl-media.com/place/6240812/8658489b-fa3e-4a38-b1bf-af5bdb5d9bd5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Healdsburg, CA from CA $144 - ![](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 [Dec 21 - Dec 22](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2025-12-21&endDate=2025-12-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2025-12-22&endDate=2025-12-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2026-01-02&endDate=2026-01-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Healdsburg Hotel Reviews ![Fairview Inn and Suites](https://images.trvl-media.com/lodging/2000000/1120000/1111500/1111427/55aee5ca_y.jpg) ### Fairview Inn and Suites 10/10 Excellent "Nice spacious suite. Loved the jet tub. Very peaceful location… Will be back…. " [](https://expedia.ca/Healdsburg-Hotels-Fairview-Inn-And-Suites.h1111427.Hotel-Information) ![Best Western Dry Creek Inn](https://images.trvl-media.com/lodging/1000000/20000/19400/19399/5ab8ae96_y.jpg) ### Best Western Dry Creek Inn 10/10 Excellent "conveniently located, room and staff exceeded expectations" [](https://expedia.ca/Healdsburg-Hotels-Dry-Creek-Inn-MOD-Collection-By-Sonesta.h19399.Hotel-Information) ![H2Hotel](https://images.trvl-media.com/lodging/4000000/3620000/3618400/3618334/92a67a3e_y.jpg) ### H2Hotel 10/10 Excellent "Everything was great from check in to the room to check out. " [](https://expedia.ca/Healdsburg-Hotels-H2hotel.h3618334.Hotel-Information) ![Hotel Healdsburg](https://images.trvl-media.com/lodging/1000000/790000/786900/786805/9d93bedd_y.jpg) ### Hotel Healdsburg 10/10 Excellent "All we expected. Continental bfast unexpectedly filling and delish" [](https://expedia.ca/Healdsburg-Hotels-Hotel-Healdsburg.h786805.Hotel-Information) ![The Madrona](https://images.trvl-media.com/lodging/1000000/460000/451700/451693/ac03bc94_y.jpg) ### The Madrona 10/10 Excellent "Love the Madrona. Absolutely beautiful property with the cutest rooms & delicious dining. " [](https://expedia.ca/Healdsburg-Hotels-The-Madrona.h451693.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Healdsburg with outdoor pools? > For a more luxurious experience, consider [H2Hotel](https://www.expedia.ca/Healdsburg-Hotels-H2hotel.h3618334.Hotel-Information), a 4-star property that not only offers a beautiful outdoor pool but also a full-service spa with a range of treatments, including massages and body wraps. Guests appreciate the lovely rooms and the helpful staff, contributing to its impressive rating of 9.4\. Located in a prime area, this hotel is great for those wanting to explore the best of Healdsburg while enjoying a relaxing retreat. > > > If you're looking for the ultimate in luxury, [Montage Healdsburg](https://www.expedia.ca/Healdsburg-Hotels-Montage-Healdsburg.h57173926.Hotel-Information) is a 5-star gem that features an exquisite outdoor pool along with poolside cabanas and a bar. With a rating of 9.6, this hotel is celebrated for its stunning views, delicious dining options, and attentive service. Families can enjoy a day by the pool while also indulging in the full-service spa amenities, ensuring a memorable stay. > > > Another luxurious option is [The Ruse](https://www.expedia.ca/Healdsburg-Hotels-The-Ruse.h89177143.Hotel-Information), also rated 9.6 by travellers. This stunning hotel features an outdoor pool, a restaurant by the poolside, and beautiful mountain views. Guests love the top service and the premium rooms, making it an excellent choice for families wanting both adventure and relaxation. > > > Lastly, [Grape Leaf Inn](https://www.expedia.ca/Healdsburg-Hotels-Grape-Leaf-Inn.h6948841.Hotel-Information), a 4-star hotel, offers a delightful outdoor pool alongside a relaxing spa experience. With a traveller rating of 9.4, this inn is much-loved for its delicious breakfast and serene atmosphere, great for families seeking a quaint getaway in Healdsburg. ### How much does a hotel with outdoor pool in Healdsburg cost? ### Are there hotels in Healdsburg with outdoor pool cabanas or loungers? > Another fantastic option is [Appellation Healdsburg](https://www.expedia.ca/Healdsburg-Hotels-Appellation-Healdsburg.h118738917.Hotel-Information), a 4.5-star hotel also boasting an outdoor pool outfitted with free cabanas and sun loungers. With a similar traveller rating of 9.6, it offers a relaxing atmosphere combined with amenities like evening entertainment and premium bedding, ensuring a comfortable stay for families and those seeking an upscale experience. ### Which Healdsburg hotels offer poolside service for food and drinks? > Another excellent option is [Appellation Healdsburg](https://www.expedia.ca/Healdsburg-Hotels-Appellation-Healdsburg.h118738917.Hotel-Information), a charming 4.5-star hotel that also features an outdoor pool complete with a poolside bar for convenient service. With the same top rating of 9.6, guests appreciate the cozy atmosphere and upscale amenities, including complimentary poolside cabanas and evening entertainment. The combination of designer toiletries and premium bedding in the beautifully appointed rooms adds to the overall appeal, creating a delightful retreat in the heart of California's wine country. ### Are there hotels with outdoor pools that are close to Russian River? > Another exceptional option is [The Ruse](https://www.expedia.ca/Healdsburg-Hotels-The-Ruse.h89177143.Hotel-Information), also a 5-star property that boasts an inviting outdoor pool and a delightful poolside restaurant. With a superb rating of 9.6, travellers appreciate the beautiful and clean rooms, as well as the top, friendly staff. Families can enjoy a round of tennis on-site or soak in the stunning mountain views while savoring a delicious breakfast. > > > For those looking for a slightly more budget-friendly option, the [Grape Leaf Inn](https://www.expedia.ca/Healdsburg-Hotels-Grape-Leaf-Inn.h6948841.Hotel-Information) offers a charming 4-star experience with an outdoor pool that provides a relaxing atmosphere after a day of exploring the nearby Russian River. Rated 9.4 by guests, this inn is complemented by a lovely winery tasting room and spa treatments, making it a delightful choice for families seeking comfort and quality. > > > Finally, [Hotel Healdsburg](https://www.expedia.ca/Healdsburg-Hotels-Hotel-Healdsburg.h786805.Hotel-Information) is a well-rated 4-star hotel featuring an outdoor pool and offering complimentary continental breakfast. Guests have highlighted the excellent location and friendly service, with a great rating of 9.2\. This hotel is superb for families looking to explore Healdsburg while enjoying a refreshing swim. ### Is it cheaper to book flights and a hotel in Healdsburg as a package? ### How can I save on a hotel in Healdsburg with Expedia? ### Can I cancel my hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Alexander Valley ](https://www.expedia.ca/Alexander-Valley-Hotels-Cheap-Hotels.0-0-d736344212904407040-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Alexander Valley ](https://www.expedia.ca/Alexander-Valley-Hotels-Luxury-Hotel.0-0-d736344212904407040-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Downtown San Francisco ](https://www.expedia.ca/Downtown-San-Francisco-San-Francisco-Hotels-All-Inclusive-Hotel.0-n6151902-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Downtown San Francisco ](https://www.expedia.ca/Downtown-San-Francisco-San-Francisco-Hotels-Golf-Hotel.0-n6151902-0-tGolfHotel.Travel-Guide-Filter-Hotels) - 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