Title: Book the Best Hotels with POOL in Cuddebackville in 2025 | Expedia.ca [Hotels in Cuddebackville](https://expedia.ca/Cuddebackville-Hotels.d3000448273.Travel-Guide-Hotels)[Vacation Rentals in Cuddebackville](https://expedia.ca/Cuddebackville-Vacation-Rentals.d3000448273.Travel-Guide-VacationRentals)[Flights to Cuddebackville](https://expedia.ca/Cheap-Flights-To-Cuddebackville.d3000448273.Travel-Guide-Flights)[Cuddebackville Car Rentals](https://expedia.ca/Car-Rentals-In-Cuddebackville.d3000448273.Car-Rental-Guide)[Cuddebackville Vacation Packages](https://expedia.ca/Cuddebackville.d3000448273.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 Cuddebackville, NY from CA $144 ![](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 Cuddebackville Hotels with a Pool Tonight [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=3000448273&startDate=2025-10-23&endDate=2025-10-24&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=3000448273&startDate=2025-10-24&endDate=2025-10-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=3000448273&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=3000448273&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cuddebackville Hotels with a Pool ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e.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) "Was a clean room and breakfast was decent" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne CA $155 CA $183 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.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) ![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) ![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) ### La Quinta Inn & Suites by Wyndham Middletown-Goshen Middletown 9.4/10 Exceptional (867) "Clean, pool, great breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eunice CA $156 CA $184 total includes taxes & fees Nov 9 - Nov 10 [](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/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) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/5b25316b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/53a095c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Goshen Middletown Goshen 8.8/10 Excellent (1002) "This place is fantastic from the staff to the rooms. Very clean. Will definitely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda CA $130 CA $160 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Newburgh-Hotels-Fairfield-Inn-Suites-By-Marriott-Goshen-Middletown.h1214332.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/93b27f1d.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) ![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 (1001) "Easy check in, clean, near restaurants. We’d stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $122 CA $144 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.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) ![Lobby](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/6da85435.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 8.2/10 Very good (13) "We loved everything from the staff to the stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Arnassia CA $320 CA $436 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Goshen-Hotels-LEGOLAND-Hotel-NEW-York.h70415091.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/70c821f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/262d6215.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/1ff4f5d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Hunt's Landing Hotel Matamoras/Milford Matamoras 8.4/10 Very good (1002) "Great staff&great area for touring. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christina CA $133 CA $145 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Matamoras-Hotels-Best-Western-Hunts-Landing-Hotel-MatamorasMilford.h27210.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) ![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/1000000/930000/921500/921424/9b61f0f6.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 Middletown 8.6/10 Excellent (1006) "The place was nice and clean. Staff was friendly. I wish the TV was updated so I could put on Netflix, but other than that it was a great stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angel CA $136 CA $160 total includes taxes & fees Nov 9 - Nov 10 [](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) ![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 Middletown 8.4/10 Very good (1003) "The hotel was great it was very clean, had plenty of parking, the staff was very friendly. Continental breakfast was great and fresh. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian CA $145 CA $171 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/34300/34237/4e850782.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Wurtsboro Wurtsboro 7.6/10 Good (568) "Perfect for our stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ines CA $143 CA $161 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Monticello-Hotels-Days-Inn-By-Wyndham-Wurtsboro.h34237.Hotel-Information) ![Indoor pool, open 7 AM to 10 PM, free cabanas, sun loungers](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/95ef3af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Concierge desk](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/e3c7f442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/ecb80f49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 King Bed](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/90e1f183.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Resorts World Catskills Casino Monticello 8.6/10 Excellent (1078) "It is a great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caonabo CA $205 CA $267 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.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=2025-11-06&endDate=2025-11-07®ionId=3000448273&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Cuddebackville Hotel Reviews ![Sleep Inn & Suites Middletown - Goshen](//images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg) ### Sleep Inn & Suites Middletown - Goshen 10/10 Excellent "Very clean and roomy, quiet A/C, nice breakfast." [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Holiday Inn Express & Suites Montgomery by IHG](//images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/98944f60_y.jpg) ### Holiday Inn Express & Suites Montgomery by IHG 10/10 Excellent "good" [](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) ![Hampton Inn Matamoras/Milford](//images.trvl-media.com/lodging/3000000/2780000/2774600/2774574/e1440092_y.jpg) ### Hampton Inn Matamoras/Milford 10/10 Excellent " Friendly" [](https://expedia.ca/Matamoras-Hotels-Hampton-Inn-Matamoras-Milford.h2774574.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chester by IHG](//images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e_y.jpg) ### Holiday Inn Express Hotel & Suites Chester by IHG 10/10 Excellent "Was a clean room and breakfast was decent" [](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Fairfield Inn & Suites by Marriott Goshen Middletown](//images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/53a095c1_y.jpg) ### Fairfield Inn & Suites by Marriott Goshen Middletown 10/10 Excellent "Clean room, breakfast was plentiful and front desk were great." [](https://expedia.ca/Newburgh-Hotels-Fairfield-Inn-Suites-By-Marriott-Goshen-Middletown.h1214332.Hotel-Information) ![Home2 Suites by Hilton Middletown](//images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/3c35a288_y.jpg) ### Home2 Suites by Hilton Middletown 10/10 Excellent "Close to Legoland , great spot to stat if you want to do 2 days at legoland." [](https://expedia.ca/Newburgh-Hotels-Home2-Suites-By-Hilton-Middletown.h15984645.Hotel-Information) ![Best Western Hunt's Landing Hotel Matamoras/Milford](//images.trvl-media.com/lodging/1000000/30000/27300/27210/5acfc319_y.jpg) ### Best Western Hunt's Landing Hotel Matamoras/Milford 10/10 Excellent "Love it" [](https://expedia.ca/Matamoras-Hotels-Best-Western-Hunts-Landing-Hotel-MatamorasMilford.h27210.Hotel-Information) ![Courtyard by Marriott Middletown Goshen](//images.trvl-media.com/lodging/1000000/930000/921500/921424/5eeeba71_y.jpg) ### Courtyard by Marriott Middletown Goshen 10/10 Excellent "Nice room" [](https://expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![Days Inn by Wyndham Wurtsboro](//images.trvl-media.com/lodging/1000000/40000/34300/34237/3073e3e0_y.jpg) ### Days Inn by Wyndham Wurtsboro 10/10 Excellent "Easy check in. Room comfortable with bed also cozy. We slept great and did not have any issues to interrupt our stay! I’m " [](https://expedia.ca/Monticello-Hotels-Days-Inn-By-Wyndham-Wurtsboro.h34237.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Cuddebackville? > [The Kartrite Resort & Indoor Waterpark](https://www.expedia.ca/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information): Hotel, 7-minute walk from Resorts World Catskills. Features a children's pool, an indoor pool, and a water park. [Resorts World Catskills Casino](https://www.expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information): Hotel, 4-minute walk from Resorts World Catskills. Offers 6 restaurants, a pool, and a full-service spa. [Sleep Inn & Suites Middletown - Goshen](https://www.expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information): Provides 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): Features 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): Offers complimentary wired internet access, an indoor pool, and free self parking. ### What is there to see and do in Cuddebackville? > Explore places like LEGOLAND® New York while you're in the area. Surround yourself with nature at Neversink River and Delaware and Hudson Canal County Park. ### When is the best time to book a hotel with a pool in Cuddebackville? > Taking into account the local weather in Cuddebackville 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 30°F. The snowiest months in Cuddebackville 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 - Flights - 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) - [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) - [Business Hotels in Central New York City](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Business-Hotel.0-n553248633938969338-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - 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