Title: Book the Best Hotels with POOL in Middletown in 2025 | 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 $131 - ![](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 [Nov 21 - Nov 22](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2025-11-21&endDate=2025-11-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 22 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2025-11-22&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Middletown Hotels with a Pool ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/0a5108cc.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) ![Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/633769f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/d1fd54a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Middletown-Goshen Middletown 9.4/10 Exceptional (917) "great staff, clean rooms, nice breakfast .. overall a pleasant & safe atmosphere !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emerson CA $154 CA $182 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.Hotel-Information) ![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/1000000/290000/282000/281932/93b27f1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/7c606992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn by Hilton Middletown Middletown 8.6/10 Excellent (1002) "Nice quiet place The workout center and breakfast were both lovely and the location was easy to find " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachael CA $113 CA $133 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/38a9650f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/046baaca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/60661c7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/5eeeba71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Middletown Goshen Middletown 8.6/10 Excellent (1002) "The hotel was very clean, enjoyed my stay would recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $130 CA $154 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/02e6ff39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/cefa7296.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 Middletown 8.6/10 Excellent (1000) "Friendly staff, clean room and great breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janet CA $143 CA $168 total includes taxes & fees Dec 21 - Dec 22 [](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) ![Property amenity](https://images.trvl-media.com/lodging/42000000/41530000/41524600/41524586/4231886e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/42000000/41530000/41524600/41524586/697f516f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds, Accessible Bathtub, Non Smoking (Comm, Mobil, Access Tub)](https://images.trvl-media.com/lodging/42000000/41530000/41524600/41524586/6bec0a1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Middletown - Goshen by IHG Middletown 8.8/10 Excellent (695) "Clean and close to shopping. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Arthur CA $182 CA $215 total includes taxes & fees Nov 23 - Nov 24 [](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) ![Lobby](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/e39f1f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/2f1506bc.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 Middletown 9.0/10 Wonderful (739) "the room was very clean, friendly staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nyowa CA $201 CA $243 total includes taxes & fees Dec 21 - Dec 22 [](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/b44e4aa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/2fad5b45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/09797bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/d400e8cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott Middletown Goshen Middletown 9.4/10 Exceptional (315) "Room and service were excellent." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cymantha CA $239 CA $282 total includes taxes & fees Dec 7 - Dec 8 [](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) ![Reception](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/92dbf0a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/09941fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Chester by IHG Chester 8.4/10 Very good (1001) "Great for a quick stay 👍" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerry CA $110 CA $131 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/2396df2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's play area - indoor](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/9834d0ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/a7704166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/5555dde6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LEGOLAND Hotel NEW York Goshen 8.6/10 Excellent (22) "We loved everything from the staff to the stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Arnassia CA $158 CA $357 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Goshen-Hotels-LEGOLAND-Hotel-NEW-York.h70415091.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) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/da52c924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9.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 Central Valley 9.2/10 Wonderful (1006) "Staff were friendly and very helpful and the hotel was well cared after. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason CA $134 CA $165 total includes taxes & fees Dec 11 - Dec 12 [](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=2025-12-05&endDate=2025-12-06®ionId=8864&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_8864) ## Top Middletown Hotel Reviews ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "new remodels rooms, nice hotel and very clean" [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 10/10 Excellent "Great job" [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.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 "Breakfast was very good, room was clean, however no information about check out, simlply no information about anyfhing" [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) ![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 "Great experience highly recommend. " [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Super 8 by Wyndham Middletown](https://images.trvl-media.com/lodging/1000000/460000/459800/459783/63cc5778_y.jpg) ### Super 8 by Wyndham Middletown 10/10 Excellent "Great location, a little aged but ok for the price." [](https://expedia.ca/Newburgh-Hotels-Super-8-By-Wyndham-Middletown.h459783.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 "Best hotel I’ve stayed in for a while. Very clean, friendly staff, very comfortable. Walking distance to everything. Breakfast was excellent. We stayed 5 nights and breakfast was different every day…. Fried eggs, scramble, omelet, sausage, bacon, empanadas, waffles, it was excellent!" [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.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 "Clean nice hotel in a very cute area with restaurants in walking distance away" [](https://expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.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 "This hotel was clean and very friendly, dogs are also allowed on the property. The room was definitely spacious especially since you basically get half of a kitchen. Breakfast was average, although the drink choices were not really good (orange and apple juice tasted very water down). Other than that, my stay was a 10/10, would definitely recommend others to visit. " [](https://expedia.ca/Newburgh-Hotels-Home2-Suites-By-Hilton-Middletown.h15984645.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Middletown? > [Sleep Inn & Suites Middletown - Goshen](https://www.expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information): Features continental, an indoor pool, and complimentary wired internet access. [La Quinta Inn & Suites by Wyndham Middletown-Goshen](https://www.expedia.ca/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.Hotel-Information): Offers daily, an indoor pool, and free self parking. [Courtyard by Marriott Middletown Goshen](https://www.expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information): Provides complimentary wired internet access, an indoor pool, and free self parking. [Super 8 by Wyndham Middletown](https://www.expedia.ca/Newburgh-Hotels-Super-8-By-Wyndham-Middletown.h459783.Hotel-Information): Offers daily, a seasonal outdoor pool, and complimentary wired internet access. [Hampton Inn by Hilton Middletown](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information): Features daily, an indoor pool, and complimentary wired internet access. ### What is there to see and do in Middletown? > Spend some time experiencing the great outdoors at Highland Lake and Thomas Bull Memorial Park. During your stay, check out sights such as Paramount Theatre, Orange County Fair Speedway, and Orange County Fairgrounds. Travelers love Middletown for its array of dining options. ### When is the best time to book a hotel with a pool in Middletown? > Taking into account the local weather in Middletown can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Middletown are January, February, March, and April, with each month seeing an average of 6 inches of snowfall. ## 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) - [Beach Hotel Hotels in Central New York City](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Beach-Hotel.0-n553248633938969338-0-tBeachHotel.Travel-Guide-Filter-Hotels) - 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