Title: Book the Best Hotels with POOL in Brewster in 2025 | Expedia.ca [Hotels in Brewster](https://expedia.ca/Brewster-Hotels.d183644.Travel-Guide-Hotels)[Vacation Rentals in Brewster](https://expedia.ca/Brewster-Vacation-Rentals.d183644.Travel-Guide-VacationRentals)[Flights to Brewster](https://expedia.ca/Cheap-Flights-To-Brewster.d183644.Travel-Guide-Flights)[Things to do in Brewster](https://expedia.ca/Things-To-Do-In-Brewster.d183644.Travel-Guide-Activities)[Brewster Car Rentals](https://expedia.ca/Car-Rentals-In-Brewster.d183644.Car-Rental-Guide)[Brewster Vacation Packages](https://expedia.ca/Brewster.d183644.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Brewster, NY from CA $189 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Brewster Hotels with a Pool Tonight [Sep 26 - Sep 27](https://www.expedia.ca/Hotel-Search?regionId=183644&startDate=2025-09-26&endDate=2025-09-27&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 27 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=183644&startDate=2025-09-27&endDate=2025-09-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=183644&startDate=2025-09-26&endDate=2025-09-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=183644&startDate=2025-10-03&endDate=2025-10-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Brewster Hotels with a Pool ![Seasonal outdoor pool, open 8:00 AM to 9:00 PM, free cabanas](https://images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/4ed8dfa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room with Kitchen (Private Entrance)](https://images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/8561ada3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/0ce6450f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/76122822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heidi's Inn Brewster 8.8/10 Excellent (787) "It was an amazing place to stay." CA $175 CA $189 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Poughkeepsie-Hotels-Heidis-Inn-Brewster-New-York.h9498859.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=2025-10-10&endDate=2025-10-11®ionId=183644&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Brewster Hotel Reviews ![The Watershed](//images.trvl-media.com/lodging/7000000/6030000/6020100/6020007/c1a1bbc5_y.jpg) ### The Watershed 10/10 Excellent "Decor, views are stunning. I want to model my new bath after the yours. " [](https://expedia.ca/Stamford-Hotels-Hotel-Zero-Degrees-Norwalk.h6020007.Hotel-Information) ![Overlook Lodge at Bear Mountain](//images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "Wonderful staff!" [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG](//images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/58071d11_y.jpg) ### Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG 10/10 Excellent "Clean and spacious. Room is bigger than expected. " [](https://expedia.ca/White-Plains-Hotels-Holiday-Inn-Express-Hotel-Suites-Peekskill-Hudson-Valley.h6541495.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Danbury](//images.trvl-media.com/lodging/1000000/20000/15100/15069/f35501d5_y.jpg) ### La Quinta Inn & Suites by Wyndham Danbury 10/10 Excellent "Overall nice experience. The Van’s pizza next door is very convenient for a drink at the bar and a bite to eat. Staff is always friendly. No complaints at all. " [](https://expedia.ca/Danbury-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Danbury.h15069.Hotel-Information) ![Inn on the Hudson](//images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/b1419d47_y.jpg) ### Inn on the Hudson 8/10 Good "The hotel was very nice. I would stay there again. Quiet at night. The view of the river is breath taking. I enjoyed morning coffee outside. The grab and go breakfast is convenient, but carb heavy for those who need to watch their sugar intake. The event space would make a great place for a party, but the patio could use some sprucing up. I enjoyed the flannel blanket between two top sheets; warm and cosey for cold nights. Wood floors are a rustic touch. Shower was great; plenty of hot water. " [](https://expedia.ca/White-Plains-Hotels-Inn-On-The-Hudson.h1148858.Hotel-Information) ![Hilton Garden Inn Norwalk](//images.trvl-media.com/lodging/1000000/590000/580400/580328/3ea4ab25_y.jpg) ### Hilton Garden Inn Norwalk 10/10 Excellent "Comfortable room " [](https://expedia.ca/Stamford-Hotels-Hilton-Garden-Inn-Norwalk.h580328.Hotel-Information) ![Heidi's Inn](//images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/0ce6450f_y.jpg) ### Heidi's Inn 10/10 Excellent "Great place. Owner was really nice and helpful. " [](https://expedia.ca/Poughkeepsie-Hotels-Heidis-Inn-Brewster-New-York.h9498859.Hotel-Information) ![Ethan Allen Hotel](//images.trvl-media.com/lodging/1000000/850000/848400/848360/9fd70ba0_y.jpg) ### Ethan Allen Hotel 10/10 Excellent "excellent! I would stay there again and recommend to friends and family" [](https://expedia.ca/Danbury-Hotels-Ethan-Allen-Hotel.h848360.Hotel-Information) ![Hotel MTK Mount Kisco](//images.trvl-media.com/lodging/1000000/30000/26800/26788/0d5d6da0_y.jpg) ### Hotel MTK Mount Kisco 10/10 Excellent "Room was beautifully appointed and clean" [](https://expedia.ca/White-Plains-Hotels-Holiday-Inn-Mt-Kisco.h26788.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Brewster? > [Heidi's Inn](https://www.expedia.ca/Poughkeepsie-Hotels-Heidis-Inn-Brewster-New-York.h9498859.Hotel-Information): Features daily, a seasonal outdoor pool, and free self parking. [Comfort Inn Brewster](https://www.expedia.ca/Poughkeepsie-Hotels-Comfort-Inn.h36486712.Hotel-Information): Hotel, 1-minute walk from Bear Mountain State Park. Features a full-service spa, a seasonal outdoor pool, and a snack bar/deli. [Microtel Inn & Suites by Wyndham Bethel/Danbury](https://www.expedia.ca/Danbury-Hotels-Microtel-Inn-Suites-By-Wyndham-BethelDanbury.h579216.Hotel-Information): Features a snack bar/deli, a seasonal outdoor pool, and free self parking. [Overlook Lodge at Bear Mountain](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information): Offers complimentary wired internet access, a pool, and free self parking. [The Watershed](https://www.expedia.ca/Stamford-Hotels-Hotel-Zero-Degrees-Norwalk.h6020007.Hotel-Information): Features daily, a seasonal outdoor pool, and free self parking. ### What is there to see and do in Brewster? > Take a walk along the waterfront at Canopus Beach and Mamanasco Beach. Discover sights such as Brewster Public Library during your stay. ### When is the best time to book a hotel with a pool in Brewster? > You may want to think about a place to stay that offers an outdoor pool if you plan to visit Brewster in the warmest months of July, August, or June when the average temp is 69°F. Lodging offering an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 32°F. ### What's the best way to travel around Brewster? > Knowing the transportation options in Brewster can help you enjoy the area beyond your hotel pool. To see more of the surrounding area, hop aboard a train at Brewster Train Station or Southeast Station. 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