Title: Book the Best Hotels with POOL in Middletown in 2026 | Expedia.ca [Hotels in Middletown](https://expedia.ca/Middletown-Hotels.d8864.Travel-Guide-Hotels)[Vacation Rentals in Middletown](https://expedia.ca/Middletown-Vacation-Rentals.d8864.Travel-Guide-VacationRentals)[Flights to Middletown](https://expedia.ca/Cheap-Flights-To-Middletown.d8864.Travel-Guide-Flights)[Things to do in Middletown](https://expedia.ca/Things-To-Do-In-Middletown.d8864.Travel-Guide-Activities)[Middletown Car Rentals](https://expedia.ca/Car-Rentals-In-Middletown.d8864.Car-Rental-Guide)[Middletown Vacation Packages](https://expedia.ca/Middletown.d8864.Destination-Travel-Guides) ![Route 17 in ny is a great road to view the fall foliage](https://images.trvl-media.com/place/8005/8b2c54c4-af30-4521-9b56-3bdf0a8d1a15.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Vincent Ramundo # Find Hotels with a Pool in Middletown, NY from CA $137 - ![](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 Middletown Hotels with a Pool Tonight [Jan 10 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-01-10&endDate=2026-01-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 11 - Jan 12](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-01-11&endDate=2026-01-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Middletown hotels with a pool ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/cf710d60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/8c9a3fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/88d2ecc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/d055a3f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn by Hilton Middletown [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) Middletown 8.6/10 Excellent (1,007 reviews) "Clean Rooms, clean hotel overall. Plenty of parking." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) KenNETH CA $118 CA $140 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/cdebce5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/26de74c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/fed7909a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/da2d7bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Middletown-Goshen [](https://www.expedia.ca/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.Hotel-Information) Middletown 9.4/10 Exceptional (950 reviews) "Room was large and spacious \~ perfect for all the luggage we brought" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $158 CA $187 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/fb63b6d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/ba2c672f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/0bd48f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/5a64b5a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Middletown Goshen [](https://www.expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) Middletown 8.6/10 Excellent (1,009 reviews) "This our half way point when we travel and we always stop here. Front desk people are always great never had a bad one yet! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Denise CA $128 CA $152 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/f7784036.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Efficiency, Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/6eb13bf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/747581be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1cbd6222.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Middletown - Goshen [](https://www.expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) Middletown 8.6/10 Excellent (1,004 reviews) "The rooms are clean and spacious, the beds are comfortable, and the breakfast is good. This hotel offers good value for an overnight stay." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Einat CA $134 CA $158 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/42000000/41530000/41524600/41524586/02e092b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/42000000/41530000/41524600/41524586/78d303c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/42000000/41530000/41524600/41524586/4231886e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/42000000/41530000/41524600/41524586/47aecc34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Middletown - Goshen by IHG [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Suites-Middletown-Goshen.h41524586.Hotel-Information) Middletown 8.8/10 Excellent (699 reviews) "Stayed on Sunday night, 12/28\. It’s a nice , modern and clean hotel. I had some mess up when booking the room with Expedia but the front desk lady resolved our issue very quickly . She was very responsive and helpful. Breakfast was very good, lots of options, the area was spotless and constantly being cleaned. There is great coffee machine in the lobby with coffee and tea station that added pleasure to our stay. The pool was nice and clean and so is gym. Would definitely come back and... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yelena CA $157 CA $186 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Suites-Middletown-Goshen.h41524586.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/e1246f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/3c35a288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/92beb582.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/27c83ba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Middletown [](https://www.expedia.ca/Newburgh-Hotels-Home2-Suites-By-Hilton-Middletown.h15984645.Hotel-Information) Middletown 9.0/10 Wonderful (749 reviews) "Room is clean and spacious, staffs are friendly and professional, highly recommended!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rocky CA $228 CA $275 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Newburgh-Hotels-Home2-Suites-By-Hilton-Middletown.h15984645.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/ea96dde2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/0da6fc7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/ccd2fb04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/21e70f22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott Middletown Goshen [](https://www.expedia.ca/Newburgh-Hotels-Residence-Inn-By-Marriott-Middletown-Goshen.h48273068.Hotel-Information) Middletown 9.4/10 Exceptional (318 reviews) "Great location, only issue we had occurred on our last night. A couple next door was arguing and cursing so loud that it woke up my wife and I. My wife called the front desk and the matter was handle rather quickly. I would definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachid CA $236 CA $278 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Newburgh-Hotels-Residence-Inn-By-Marriott-Middletown-Goshen.h48273068.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/64788546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/1a5890e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/308be1ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/2d8c93f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Chester by IHG [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) Chester 8.6/10 Excellent (1,004 reviews) "timely & courteous check-in; clean rooms; quiet environment; perfect location for our needs " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Orlando CA $125 CA $148 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/5acfc319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/w5760h3835x0y5-98965903.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/ab56e4cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/95f0eb53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Hunt's Landing Hotel Matamoras/Milford [](https://www.expedia.ca/Matamoras-Hotels-Best-Western-Hunts-Landing-Hotel-MatamorasMilford.h27210.Hotel-Information) Matamoras 8.4/10 Very good (1,003 reviews) "The staff were great, nice lobby, clean rooms. Only downsides were the bathrooms haven’t been updated in many years, and the breakfast was subpar. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olivia CA $126 CA $137 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Matamoras-Hotels-Best-Western-Hunts-Landing-Hotel-MatamorasMilford.h27210.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/40a70d08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room | Living area](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/7a9acd26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/e0fcb0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/9631af0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Harriman Woodbury [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) Central Valley 9.2/10 Wonderful (1,031 reviews) "Easy check in, clean room, very good breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $135 CA $167 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.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=2026-01-24&endDate=2026-01-25®ionId=8864&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Middletown Hotel Reviews ![Overlook Lodge at Bear Mountain](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "I was very happy with my stay, the room was very cozy and the surrounding areas were breathtaking " [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Mountain Creek](https://images.trvl-media.com/lodging/3000000/2900000/2899900/2899900/f09dc021_y.jpg) ### Mountain Creek 10/10 Excellent "Cozy and comfortable bed!" [](https://expedia.ca/Vernon-Hotels-Mountain-Creek.h2899900.Hotel-Information) ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg) ### Sleep Inn & Suites Middletown - Goshen 10/10 Excellent "Check in was easy Nice quiet room Continental breakfast all weekend even though the listing said it was just weekdays. Used the extra blankets in the closet as I like it extra cozy. Loved the in room coffee maker for coffee and tea water. Quick checkout. Economical! Will stay again! " [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Hampton Inn by Hilton Middletown](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/8c9a3fbd_y.jpg) ### Hampton Inn by Hilton Middletown 10/10 Excellent "Clean Rooms, clean hotel overall. Plenty of parking." [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Great Staff" [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Best Western Hunt's Landing Hotel Matamoras/Milford](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/5acfc319_y.jpg) ### Best Western Hunt's Landing Hotel Matamoras/Milford 10/10 Excellent "Helpful front desk. Clean room. Hot tea on s cold day" [](https://expedia.ca/Matamoras-Hotels-Best-Western-Hunts-Landing-Hotel-MatamorasMilford.h27210.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e_y.jpg) ### Holiday Inn Express Hotel & Suites Chester by IHG 10/10 Excellent "Yankee the hotel manager was great. Elevator was out of order but it was still amazing. She was so lovely and accommodating. The place was under construction but rooms were clean and spacious and pool and gym were nice " [](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Home2 Suites by Hilton Middletown](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/3c35a288_y.jpg) ### Home2 Suites by Hilton Middletown 10/10 Excellent "Room is clean and spacious, staffs are friendly and professional, highly recommended!" [](https://expedia.ca/Newburgh-Hotels-Home2-Suites-By-Hilton-Middletown.h15984645.Hotel-Information) ![Courtyard by Marriott Middletown Goshen](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/5eeeba71_y.jpg) ### Courtyard by Marriott Middletown Goshen 10/10 Excellent "Great room sizes. Clean and great staff" [](https://expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Middletown with outdoor pools? > Another excellent choice is the [Hampton Inn by Hilton Middletown](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information), which also boasts an outdoor pool. Families appreciate the spacious and clean rooms, as well as the fresh breakfast provided each morning at no extra charge. With its convenient yet quiet location, this hotel offers a peaceful retreat, alongside free amenities like WiFi and toiletries, ensuring a comfortable stay for everyone. > > > Both of these hotels have received commendable reviews, with the Holiday Inn Express rated 8.8 and the Hampton Inn at 8.6, reflecting the quality service and experience you can expect during your visit. ### How much does a hotel with outdoor pool in Middletown cost? ### Are there hotels with outdoor pools that are close to Galleria at Crystal Run? > Guests rave about the spacious and clean rooms, making it a comfortable base for your adventures. The outdoor pool is described as nice and well-maintained, superb for a refreshing dip after a day of shopping or exploring. > > > Additionally, the Hampton Inn offers a variety of convenient amenities that enhance your stay. Enjoy complimentary WiFi, free self-parking, and a delicious free continental breakfast that guests often mention as fresh and satisfying. Families traveling with young children will benefit from the availability of cribs at no extra charge. ### Is it cheaper to book flights and a hotel in Middletown as a package? ### How can I save on a hotel in Middletown 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 Bloomingburg ](https://www.expedia.ca/Bloomingburg-Hotels-Cheap-Hotels.0-0-d3000448043-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Bloomingburg ](https://www.expedia.ca/Bloomingburg-Hotels-Hotel-With-Pool.0-0-d3000448043-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Campbell Hall ](https://www.expedia.ca/Campbell-Hall-Hotels-Cheap-Hotels.0-0-d6338665-tCheapHotels.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Adults-Only-Resorts.0-n553248633938969338-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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