Title: The Best Hotels with a Pool in Middletown from $105 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 24 - Feb 25](https://www.expedia.com/Hotel-Search?regionId=180934&startDate=2026-02-24&endDate=2026-02-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 25 - Feb 26](https://www.expedia.com/Hotel-Search?regionId=180934&startDate=2026-02-25&endDate=2026-02-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=180934&startDate=2026-02-27&endDate=2026-03-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=180934&startDate=2026-03-06&endDate=2026-03-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Middletown hotels with a pool ![Sauna](https://images.trvl-media.com/lodging/10000000/9450000/9444400/9444378/6c68fdfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed, Poolside | Hypo-allergenic bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/10000000/9450000/9444400/9444378/788e7723.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 (1,010 reviews) "Great location, clean room, quiet and perfect for our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michele $119 nightly $137 total Feb 26 - Feb 27 Total with taxes and fees [](https://www.expedia.com/St-Helena-Hotels-El-Bonita-Motel.h9444378.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) | 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) ![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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1250000/1249600/1249559/7965154c.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 (1,001 reviews) "We LOVE the Tuscan suite! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela $147 nightly $168 total Feb 25 - Feb 26 Total with taxes and fees [](https://www.expedia.com/Geyserville-Hotels-Geyserville-Inn.h1249559.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/11000000/10230000/10226100/10226090/af082332.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/11000000/10230000/10226100/10226090/e951fd47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![36-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/11000000/10230000/10226100/10226090/00f49389.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![36-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/11000000/10230000/10226100/10226090/c2cfd360.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wydown Hotel [](https://www.expedia.com/St-Helena-Hotels-Wydown-Hotel.h10226090.Hotel-Information) St. Helena 9.8/10 Exceptional (351 reviews) "Michael and Sabrina were most welcoming. The woman who served the wonderful breakfast was equally kind and thoughtful. The room was comfortable and quiet. I hope to be a repeat guest at this charming hotel. The freshly baked chocolate chip cookie was delicious, too!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) beryl $184 nightly $212 total Feb 25 - Feb 26 Total with taxes and fees [](https://www.expedia.com/St-Helena-Hotels-Wydown-Hotel.h10226090.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) ![Body treatments, aromatherapy, hot stone massages, deep-tissue massages](https://images.trvl-media.com/lodging/119000000/118740000/118739000/118738917/bc9aaa3c.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 (50 reviews) "Beautiful resort!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer $281 nightly $327 total Feb 25 - Feb 26 Total with taxes and fees [](https://www.expedia.com/Healdsburg-Hotels-Appellation-Healdsburg.h118738917.Hotel-Information) ![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) ![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) ![Suite (Wine Country) | In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/19400/19399/542d60a8.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 (1,009 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 $109 nightly $126 total Feb 25 - Feb 26 Total with taxes and fees [](https://www.expedia.com/Healdsburg-Hotels-Dry-Creek-Inn-MOD-Collection-By-Sonesta.h19399.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) ![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) ![Courtyard](https://images.trvl-media.com/lodging/10000000/9860000/9857000/9856954/7f7164aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9860000/9857000/9856954/057bcc16.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 (1,005 reviews) "Great location - very clean, lovely staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth $149 nightly $171 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Calistoga-Hotels-Golden-Haven-Hot-Springs.h9856954.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) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1620000/1613300/1613295/25289958.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1620000/1613300/1613295/dd087900.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 (885 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 $105 nightly $117 total Feb 26 - Feb 27 Total with taxes and fees [](https://www.expedia.com/Clear-Lake-Hotels-Skylark-Shores-Resort.h1613295.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/919800/919721/16a4fb6d.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) ### 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 (2,192 reviews) "Clean room, friendly staff and great pool/hot tub area" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon $90 nightly $105 total Feb 27 - Feb 28 Total with taxes and fees [](https://www.expedia.com/Santa-Rosa-Hotels-The-Sandman.h919721.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/84000000/83130000/83127100/83127055/e9b50071.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83130000/83127100/83127055/ebb56a30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/84000000/83130000/83127100/83127055/b71aa388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/84000000/83130000/83127100/83127055/03c41ae0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Santa Rosa Sonoma Wine Country [](https://www.expedia.com/Santa-Rosa-Hotels-Hampton-Inn-Suites-Santa-Rosa-Sonoma-Wine-Country.h83127055.Hotel-Information) Santa Rosa 9.6/10 Exceptional (476 reviews) "Staff were amazing, room was clean. This was our second time staying here. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Becky $118 nightly $137 total Mar 5 - Mar 6 Total with taxes and fees [](https://www.expedia.com/Santa-Rosa-Hotels-Hampton-Inn-Suites-Santa-Rosa-Sonoma-Wine-Country.h83127055.Hotel-Information) ![Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/6000/5969/ef600db1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6000/5969/f1a23991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily full breakfast for a fee](https://images.trvl-media.com/lodging/1000000/10000/6000/5969/2c6069a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, Multiple Beds, Non Smoking | In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/6000/5969/c7d20291.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Garden Inn [](https://www.expedia.com/Santa-Rosa-Hotels-Best-Western-Garden-Inn.h5969.Hotel-Information) Santa Rosa 8.8/10 Excellent (1,003 reviews) "Front desk staff was very helpful! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David $102 nightly $118 total Mar 7 - Mar 8 Total with taxes and fees [](https://www.expedia.com/Santa-Rosa-Hotels-Best-Western-Garden-Inn.h5969.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=2026-03-10&endDate=2026-03-11®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 ![Rancho Caymus Inn](https://images.trvl-media.com/lodging/20000000/19110000/19106800/19106756/55db9461_y.jpg) ### Rancho Caymus Inn 10/10 Excellent "Friendly and knowledgeable staff, great location and charming set up, nice facility and good size rooms make it a perfect stay in the wine country. " [](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 "The room was clean and comfortable, the spa and mud bath were a unique experience. Shout out to Oscar at the mud bath, a lovely person." [](https://expedia.com/Calistoga-Hotels-Golden-Haven-Hot-Springs.h9856954.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 " [](https://expedia.com/Santa-Rosa-Hotels-Flamingo-Resort-Spa-Santa-Rosa-Sonoma.h10357.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 "Amazing staff and place to stay. " [](https://expedia.com/Calistoga-Hotels-Calistoga-Motor-Lodge-And-Spa.h94121.Hotel-Information) ![Harvest Inn](https://images.trvl-media.com/lodging/1000000/530000/527100/527073/1943198c_y.jpg) ### Harvest Inn 10/10 Excellent "Every thing was great " [](https://expedia.com/St-Helena-Hotels-Harvest-Inn.h527073.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 "I stay here every time I go to Calistoga I enjoy every stay the only thing I don’t care for it’s the breakfast it’s literally a cup of coffee and a toast not really breakfast " [](https://expedia.com/Calistoga-Hotels-Mount-View-Hotel-Spa.h26963.Hotel-Information) ![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 "Great value. Chic property and surprisingly decent breakfast. " [](https://expedia.com/Santa-Rosa-Hotels-The-Sandman.h919721.Hotel-Information) ![El Bonita Motel](https://images.trvl-media.com/lodging/10000000/9450000/9444400/9444378/f785b229_y.jpg) ### El Bonita Motel 10/10 Excellent "Newly remodeled and comfy beds and pillows. A great place to stay. We loved it before the remodel. " [](https://expedia.com/St-Helena-Hotels-El-Bonita-Motel.h9444378.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 free s’mores were great at the fire pit. Great room and waking distance to great restaurants " [](https://expedia.com/Santa-Rosa-Hotels-Hyatt-Regency-Sonoma-Wine-Country.h881709.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) - [Rv Parks in Harbin Springs ](https://www.expedia.com/Harbin-Springs-RV-Parks.d553248635975849502-aaRVParks.Travel-Guide-Accommodation) - [Resorts & Hotels with Spas in Hidden Valley Lake ](https://www.expedia.com/Hidden-Valley-Lake-Hotels-Spa-Hotel.0-0-d553248635592781690-tSpaHotel.Travel-Guide-Filter-Hotels) - 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