Title: The Best Hotels with a Pool in Middletown from $106 in 2026 | Expedia.com [Middletown Travel Guide](https://expedia.com/Middletown.dx180934)[Hotels in Middletown](https://expedia.com/Middletown-Hotels.d180934.Travel-Guide-Hotels)[Vacation Rentals in Middletown](https://expedia.com/Middletown-Vacation-Rentals.d180934.Travel-Guide-VacationRentals)[Flights to Middletown](https://expedia.com/Cheap-Flights-To-Middletown.d180934.Travel-Guide-Flights)[Car Rentals in Middletown](https://expedia.com/Car-Rentals-In-Middletown.d180934.Car-Rental-Guide)[Middletown Vacation Packages](https://expedia.com/Middletown.d180934.Destination-Travel-Guides) ![Awesome place just to relax. ](https://images.trvl-media.com/place/180934/0cf53fed-8c67-4d1d-be6d-adcfe858199c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Matthew Walls ![](https://images.trvl-media.com/place/180934/0cf53fed-8c67-4d1d-be6d-adcfe858199c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Middletown Hotels with a Pool Tonight [Feb 11 - Feb 12](https://www.expedia.com/Hotel-Search?regionId=180934&startDate=2026-02-11&endDate=2026-02-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 12 - Feb 13](https://www.expedia.com/Hotel-Search?regionId=180934&startDate=2026-02-12&endDate=2026-02-13&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 13 - Feb 15](https://www.expedia.com/Hotel-Search?regionId=180934&startDate=2026-02-13&endDate=2026-02-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=180934&startDate=2026-02-20&endDate=2026-02-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Middletown hotels with a pool ![Outdoor pool, open 7:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/19400/19399/5283d5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19400/19399/4cab251e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Wine Country) | In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/19400/19399/82de180a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19400/19399/8490e741.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dry Creek Inn MOD Collection by Sonesta [](https://www.expedia.com/Healdsburg-Hotels-Dry-Creek-Inn-MOD-Collection-By-Sonesta.h19399.Hotel-Information) Healdsburg 8.0/10 Very Good (1,004 reviews) "Clean, quiet, hospitable, affordable and very close to all the activities in Healdsburg." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela $117 nightly $136 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Healdsburg-Hotels-Dry-Creek-Inn-MOD-Collection-By-Sonesta.h19399.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1620000/1613300/1613295/fe28bfe8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1620000/1613300/1613295/dd087900.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1620000/1613300/1613295/481670e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1620000/1613300/1613295/25289958.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Skylark Shores Resort [](https://www.expedia.com/Clear-Lake-Hotels-Skylark-Shores-Resort.h1613295.Hotel-Information) Lakeport 8.2/10 Very Good (882 reviews) "Beautiful views of the lake. Great property and friendly front desk!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Doug $106 nightly $118 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Clear-Lake-Hotels-Skylark-Shores-Resort.h1613295.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1250000/1249600/1249559/94f22e84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (King Suite) | Living area | 50-inch TV with cable channels](https://images.trvl-media.com/lodging/2000000/1250000/1249600/1249559/382da479.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/2000000/1250000/1249600/1249559/08a0d0e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (King Suite) | In-room safe, iron/ironing board, cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/2000000/1250000/1249600/1249559/cfd74741.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Geyserville Inn [](https://www.expedia.com/Geyserville-Hotels-Geyserville-Inn.h1249559.Hotel-Information) Geyserville 9.2/10 Wonderful (1,000 reviews) "We LOVE the Tuscan suite! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela $147 nightly $168 total Feb 16 - Feb 17 Total with taxes and fees [](https://www.expedia.com/Geyserville-Hotels-Geyserville-Inn.h1249559.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/7000000/6300000/6293500/6293439/b50502a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6300000/6293500/6293439/w2000h1759x0y1-de6f34dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6300000/6293500/6293439/16fea92b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family dining](https://images.trvl-media.com/lodging/7000000/6300000/6293500/6293439/e36254e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Le Petit Pali St. Helena [](https://www.expedia.com/St-Helena-Hotels-Le-Petit-Pali-St-Helena.h6293439.Hotel-Information) St. Helena 10/10 Exceptional (36 reviews) "The room was amazing, great view and amenities are superb. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janelle $300 nightly $346 total Feb 26 - Feb 27 Total with taxes and fees [](https://www.expedia.com/St-Helena-Hotels-Le-Petit-Pali-St-Helena.h6293439.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) ![Dining](https://images.trvl-media.com/lodging/119000000/118740000/118739000/118738917/eb671f40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/119000000/118740000/118739000/118738917/e8f2b209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, Tempur-Pedic beds, in-room safe](https://images.trvl-media.com/lodging/119000000/118740000/118739000/118738917/1acafb74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Appellation Healdsburg [](https://www.expedia.com/Healdsburg-Hotels-Appellation-Healdsburg.h118738917.Hotel-Information) Healdsburg 9.0/10 Wonderful (46 reviews) "Beautiful resort!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer $256 nightly $298 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Healdsburg-Hotels-Appellation-Healdsburg.h118738917.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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/920000/919800/919721/6551e7d3.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) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/920000/919800/919721/d1dc54b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel [](https://www.expedia.com/Santa-Rosa-Hotels-The-Sandman.h919721.Hotel-Information) Santa Rosa 8.4/10 Very Good (2,176 reviews) "Clean room, friendly staff and great pool/hot tub area" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon $91 nightly $106 total Feb 17 - Feb 18 Total with taxes and fees [](https://www.expedia.com/Santa-Rosa-Hotels-The-Sandman.h919721.Hotel-Information) ![Sauna](https://images.trvl-media.com/lodging/10000000/9450000/9444400/9444378/6c68fdfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/10000000/9450000/9444400/9444378/115ae849.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/10000000/9450000/9444400/9444378/cd679390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples dining](https://images.trvl-media.com/lodging/10000000/9450000/9444400/9444378/ed91ae44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### El Bonita Motel [](https://www.expedia.com/St-Helena-Hotels-El-Bonita-Motel.h9444378.Hotel-Information) St. Helena 9.2/10 Wonderful (1,011 reviews) "Great location, clean room, quiet and perfect for our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michele $129 nightly $149 total Feb 16 - Feb 17 Total with taxes and fees [](https://www.expedia.com/St-Helena-Hotels-El-Bonita-Motel.h9444378.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/10000000/9860000/9857000/9856954/cde0eb66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/10000000/9860000/9857000/9856954/23cd9c0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/10000000/9860000/9857000/9856954/7f7164aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room | Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/10000000/9860000/9857000/9856954/a66bc4c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Golden Haven Hot Springs [](https://www.expedia.com/Calistoga-Hotels-Golden-Haven-Hot-Springs.h9856954.Hotel-Information) Calistoga 9.4/10 Exceptional (998 reviews) "Great location - very clean, lovely staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth $149 nightly $171 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Calistoga-Hotels-Golden-Haven-Hot-Springs.h9856954.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) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83700000/83691500/83691429/ed6e99e0.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/dff5470c.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) ### The Lodge at Healdsburg, Tapestry Collection by Hilton [](https://www.expedia.com/Healdsburg-Hotels-The-Lodge-At-Healdsburg.h83691429.Hotel-Information) Healdsburg 9.0/10 Wonderful (433 reviews) "Helpful staff, clean, modern, great shower. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Christina $169 nightly $196 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/Healdsburg-Hotels-The-Lodge-At-Healdsburg.h83691429.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273394/e43ebe8c.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273394/1aee19ff.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) ### Holiday Inn Express® Windsor Sonoma Wine Country by IHG [](https://www.expedia.com/Windsor-Hotels-Holiday-Inn-Express-Windsor-Sonoma-Wine-Country.h1273394.Hotel-Information) Windsor 9.2/10 Wonderful (1,304 reviews) "Hotel was very clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rene $103 nightly $117 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Windsor-Hotels-Holiday-Inn-Express-Windsor-Sonoma-Wine-Country.h1273394.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.com/Hotel-Search?startDate=2026-02-26&endDate=2026-02-27®ionId=180934&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Middletown Breakfast included 4 stars Ocean view Hot tub 5 stars ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AFFINITY_SPRING_PROMO_180934) ## Top Middletown Hotel Reviews ![The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/920000/919800/919721/6551e7d3_y.jpg) ### The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel 10/10 Excellent "Room and bathroom were a generous size, room was clean. I would for sure stay here again. Close to Sonoma airport, and centrally located downtown Santa Rosa and restaurants in Sonoma and Napa. " [](https://expedia.com/Santa-Rosa-Hotels-The-Sandman.h919721.Hotel-Information) ![Rancho Caymus Inn](https://images.trvl-media.com/lodging/20000000/19110000/19106800/19106756/55db9461_y.jpg) ### Rancho Caymus Inn 10/10 Excellent "The staff was wonderful. " [](https://expedia.com/St-Helena-Hotels-Rancho-Caymus-Inn.h19106756.Hotel-Information) ![Golden Haven Hot Springs](https://images.trvl-media.com/lodging/10000000/9860000/9857000/9856954/cde0eb66_y.jpg) ### Golden Haven Hot Springs 10/10 Excellent "Excellent!" [](https://expedia.com/Calistoga-Hotels-Golden-Haven-Hot-Springs.h9856954.Hotel-Information) ![Calistoga Motor Lodge and Spa](https://images.trvl-media.com/lodging/1000000/100000/94200/94121/0c2722fb_y.jpg) ### Calistoga Motor Lodge and Spa 10/10 Excellent "It was a charming, well-curated property. They did a great job transforming a motel into a cute, modern version. It would be even better if the front-side rooms had pendant lighting or window shutters to add a bit more character. The room was clean and comfortable. If I had to mention one downside, it would be the water pressure, which could be improved." [](https://expedia.com/Calistoga-Hotels-Calistoga-Motor-Lodge-And-Spa.h94121.Hotel-Information) ![El Bonita Motel](https://images.trvl-media.com/lodging/10000000/9450000/9444400/9444378/f785b229_y.jpg) ### El Bonita Motel 10/10 Excellent "Everything was great! Clean refurbished since we were there last! " [](https://expedia.com/St-Helena-Hotels-El-Bonita-Motel.h9444378.Hotel-Information) ![UpValley Inn & Hot Springs Napa Valley, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/21200/21123/4454bcc5_y.jpg) ### UpValley Inn & Hot Springs Napa Valley, an Ascend Collection Hotel 10/10 Excellent "This is the eight time I stayed in this resort I love it" [](https://expedia.com/Calistoga-Hotels-UpValley-Inn-Hot-Springs.h21123.Hotel-Information) ![Mount View Hotel & Spa](https://images.trvl-media.com/lodging/1000000/30000/27000/26963/a0d0b5bd_y.jpg) ### Mount View Hotel & Spa 10/10 Excellent "Loved the location, the pool and spa, the restaurant and rum room and our cottage. Would definitely stay again!" [](https://expedia.com/Calistoga-Hotels-Mount-View-Hotel-Spa.h26963.Hotel-Information) ![Hyatt Regency Sonoma Wine Country](https://images.trvl-media.com/lodging/1000000/890000/881800/881709/1114123a_y.jpg) ### Hyatt Regency Sonoma Wine Country 10/10 Excellent "The room was spotless, but the staff were terrific! Particularly Hajar at the front desk." [](https://expedia.com/Santa-Rosa-Hotels-Hyatt-Regency-Sonoma-Wine-Country.h881709.Hotel-Information) ![Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton](https://images.trvl-media.com/lodging/1000000/20000/10400/10357/ded94e64_y.jpg) ### Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton 10/10 Excellent "Great stay" [](https://expedia.com/Santa-Rosa-Hotels-Flamingo-Resort-Spa-Santa-Rosa-Sonoma.h10357.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Middletown? ### What is there to see and do in Middletown? ### When is the best time to book a hotel with a pool in Middletown? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Beaver Creek Vineyards ](https://www.expedia.com/Beaver-Creek-Vineyards-Hotels.0-l6335693-0.Travel-Guide-Filter-Hotels) - [Hotels near Twin Pine Casino ](https://www.expedia.com/Twin-Pine-Casino-Hotels.0-l553248621532640814-0.Travel-Guide-Filter-Hotels) - 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