Title: Book the Best Hotels with POOL in Cragsmoor in 2026 | Expedia.ca [Hotels in Cragsmoor](https://expedia.ca/Cragsmoor-Hotels.d3000448265.Travel-Guide-Hotels)[Vacation Rentals in Cragsmoor](https://expedia.ca/Cragsmoor-Vacation-Rentals.d3000448265.Travel-Guide-VacationRentals)[Cragsmoor Car Rentals](https://expedia.ca/Car-Rentals-In-Cragsmoor.d3000448265.Car-Rental-Guide)[Cragsmoor Vacation Packages](https://expedia.ca/Cragsmoor.d3000448265.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Cragsmoor, NY from CA $129 - ![](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 Cragsmoor Hotels with a Pool Tonight [Dec 24 - Dec 25](https://www.expedia.ca/Hotel-Search?regionId=3000448265&startDate=2025-12-24&endDate=2025-12-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 25 - Dec 26](https://www.expedia.ca/Hotel-Search?regionId=3000448265&startDate=2025-12-25&endDate=2025-12-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000448265&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=3000448265&startDate=2026-01-02&endDate=2026-01-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Cragsmoor 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) ![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) ![Premium bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/112cd2bf.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 (1001) "Room was clean and staff was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Annemarie CA $109 CA $129 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bdaa6450.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/a9b4d40a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/7df797b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn by Hilton New Paltz [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) New Paltz 9.4/10 Exceptional (1000) "The hotel is quiet and clean and had a very comfortable bed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carolyn CA $167 CA $187 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/046baaca.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 (1004) "The hotel was very clean, enjoyed my stay would recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $127 CA $150 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/d2d7994a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/c4928040.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/067fc37c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/5b25316b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Goshen Middletown [](https://www.expedia.ca/Newburgh-Hotels-Fairfield-Inn-Suites-By-Marriott-Goshen-Middletown.h1214332.Hotel-Information) Goshen 8.8/10 Excellent (1001) "Rooms were clean and as expected. Bed was a bit soft for our taste, but acceptable. Breakfast options were routine, scrambled eggs, bacon or sausage on alternating days, oatmeal, waffles, bagel, toast, English muffins... Pleasant and helpful staff, smooth check-in and check-out. Overall a pleasant place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joon CA $138 CA $170 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Newburgh-Hotels-Fairfield-Inn-Suites-By-Marriott-Goshen-Middletown.h1214332.Hotel-Information) ![Indoor pool, open 6 AM to 11 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/9b9c3b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/b3546f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/w4000h2662x0y0-618f3f1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/7494afa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Newburgh Stewart Airport [](https://www.expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Newburgh-Stewart-Airport.h42673.Hotel-Information) Newburgh 8.2/10 Very good (698) "Property clean rooms clean front desk the Best " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dirwin CA $133 CA $157 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Newburgh-Stewart-Airport.h42673.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/0a5108cc.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/77a42b8a.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 (941) "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 $162 CA $191 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/40000/34300/34237/3c1f5497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking (1 Bedroom)](https://images.trvl-media.com/lodging/1000000/40000/34300/34237/2ebdd972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/40000/34300/34237/3073e3e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/40000/34300/34237/5efb2487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Wurtsboro [](https://www.expedia.ca/Monticello-Hotels-Days-Inn-By-Wyndham-Wurtsboro.h34237.Hotel-Information) Wurtsboro 7.6/10 Good (596) "Very clean and quiet " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeanette CA $130 CA $147 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Monticello-Hotels-Days-Inn-By-Wyndham-Wurtsboro.h34237.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) ![Lobby](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/747581be.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) ### Sleep Inn & Suites Middletown - Goshen [](https://www.expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) Middletown 8.6/10 Excellent (1000) "Love this hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $141 CA $166 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/26600/26518/cd3eed20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Kitchenette (Living Room;with Sofabed)](https://images.trvl-media.com/lodging/1000000/30000/26600/26518/2c9f1032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26600/26518/91f35d31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26600/26518/399979ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Monticello [](https://www.expedia.ca/Monticello-Hotels-Best-Western-Monticello.h26518.Hotel-Information) Monticello 8.2/10 Very good (1000) "Awesome place to stay" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Mitchell CA $126 CA $143 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Monticello-Hotels-Best-Western-Monticello.h26518.Hotel-Information) ![Waterslide](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/90ceac4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/89050c13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/2309e5e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/w963h620x26y37-b83c1234.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Kartrite Resort & Indoor Waterpark [](https://www.expedia.ca/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information) Monticello 8.2/10 Very good (1876) "Friendly staff , clean , beautiful design in the hotel and decor . " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lusvianca CA $209 CA $324 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.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=2026-01-07&endDate=2026-01-08®ionId=3000448265&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Cragsmoor Hotel Reviews ![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 "Wonderful stay rate’s very reasonable room very clean and quiet. Staff was very inviting and helpful. Looking forward to staying again went in the Middletown New York area" [](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 "Room was not vacuumed, especially the bathroom area, several hairs were on the toilet and floor. " [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) ![Americas Best Value Inn New Paltz](https://images.trvl-media.com/lodging/1000000/900000/897900/897882/1c07aec9_y.jpg) ### Americas Best Value Inn New Paltz 10/10 Excellent "All the staff were wonderful, everything was super clean. The price was amazing. It was fairly quiet. Not super fancy at all but no complaints for the price. It was a great stay!" [](https://expedia.ca/Poughkeepsie-Hotels-Americas-Best-Value-Inn-New-Paltz.h897882.Hotel-Information) ![Hampton Inn & Suites Newburgh Stewart Airport](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/3df08b3c_y.jpg) ### Hampton Inn & Suites Newburgh Stewart Airport 10/10 Excellent "Our room was immaculate with every needed amenity! Our host was kind and courteous beyond measure, going above and beyond the call of duty!" [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Suites-Newburgh-Stewart-Airport.h17262186.Hotel-Information) ![Holiday Inn Express & Suites Montgomery by IHG](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/98944f60_y.jpg) ### Holiday Inn Express & Suites Montgomery by IHG 10/10 Excellent "clean and warm" [](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) ![Hampton Inn by Hilton New Paltz](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb_y.jpg) ### Hampton Inn by Hilton New Paltz 10/10 Excellent "All excellent " [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![Homewood Suites Stewart Airport](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/771d3275_y.jpg) ### Homewood Suites Stewart Airport 10/10 Excellent "Excellent room extremely clean and amazing and helpful staff" [](https://expedia.ca/Newburgh-Hotels-Homewood-Suites-Stewart-Airport.h1764709.Hotel-Information) ![Fairfield Inn & Suites by Marriott Goshen Middletown](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/53a095c1_y.jpg) ### Fairfield Inn & Suites by Marriott Goshen Middletown 10/10 Excellent "Room was clean and convenient. Roll in shower as requested. Breakfast adequate. Need more handicapped parking" [](https://expedia.ca/Newburgh-Hotels-Fairfield-Inn-Suites-By-Marriott-Goshen-Middletown.h1214332.Hotel-Information) ![Days Inn by Wyndham Liberty](https://images.trvl-media.com/lodging/1000000/20000/19400/19381/e60bb869_y.jpg) ### Days Inn by Wyndham Liberty 10/10 Excellent "Been staying here for 30 years and it’s nice to see they are remodeling rooms. " [](https://expedia.ca/Monticello-Hotels-Days-Inn-By-Wyndham-Liberty.h19381.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Cragsmoor? ### What is there to see and do in Cragsmoor? ### When is the best time to book a hotel with a pool in Cragsmoor? ## Explore a world of travel with Expedia - Lodging - Flights - More ways to book - [Cheap Hotels in Accord ](https://www.expedia.ca/Accord-Hotels-Cheap-Hotels.0-0-d6345617-tCheapHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Accord ](https://www.expedia.ca/Accord-Hotels-Romantic-Hotel.0-0-d6345617-tRomanticHotel.Travel-Guide-Filter-Hotels) - [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) - [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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