Title: Book the Best Brewster WINERY Hotels in 2026 | 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) ![East Branch Reservoir in Brewster New York](https://images.trvl-media.com/place/183644/6f27c7a3-5688-4530-9f7d-55c36bf42038.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Brewster, NY from CA $143 - ![](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 Brewster Winery Hotels Tonight [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=183644&startDate=2025-12-12&endDate=2025-12-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=183644&startDate=2025-12-13&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=183644&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=183644&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Brewster hotels with winery ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/7271a3ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/afb43ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/75a6f271.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/bc5eecd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus The Inn & Suites At The Falls [](https://www.expedia.ca/Poughkeepsie-Hotels-Best-Western-Plus-The-Inn-Suites-At-The-Falls.h216870.Hotel-Information) Red Oaks Mill 7.6/10 Good (437) "Nice and quaint hotel with beautiful creek behind surrounded by a dorest" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hiram CA $144 CA $163 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Poughkeepsie-Hotels-Best-Western-Plus-The-Inn-Suites-At-The-Falls.h216870.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/f57ee72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/c73b0205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/de450357.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/f3387c76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Fishkill [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Fishkill.h119273.Hotel-Information) Fishkill 8.6/10 Excellent (1000) "Clean, friendly, nice pool!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kate CA $127 CA $143 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Fishkill.h119273.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/1000000/20000/15100/15069/c07c20b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/15100/15069/ae11cdf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/15100/15069/feaf5d5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Arcade](https://images.trvl-media.com/lodging/1000000/20000/15100/15069/cb5c00ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Danbury [](https://www.expedia.ca/Danbury-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Danbury.h15069.Hotel-Information) Danbury 8.4/10 Very good (1000) "Friendly staff and clean rooms always makes for a great stay!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sam CA $148 CA $170 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Danbury-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Danbury.h15069.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/2831de3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/f4de9a4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/3b6f022d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/e02a568f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Fishkill [](https://www.expedia.ca/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.Hotel-Information) Fishkill 8.6/10 Excellent (1006) "Brayden was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Will CA $126 CA $143 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83960000/83956600/83956513/e2bb337d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/84000000/83960000/83956600/83956513/7e730f62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83960000/83956600/83956513/667341b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83960000/83956600/83956513/307575d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly. [](https://www.expedia.ca/Carmel-Hotels-Cozy-Cabin-With-Deck-And-Fireplace-Steps-From-White-Pond-Lake-Dog-Friendly.h83956513.Hotel-Information) Carmel 10/10 Exceptional (3) "It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Varuna S. CA $150 CA $324 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Carmel-Hotels-Cozy-Cabin-With-Deck-And-Fireplace-Steps-From-White-Pond-Lake-Dog-Friendly.h83956513.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/112000000/111830000/111828700/111828646/07823851.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111830000/111828700/111828646/a64ee713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111830000/111828700/111828646/fb67eeb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/112000000/111830000/111828700/111828646/42d46387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New One Bedroom Apartment Centrally Located in Southbury [](https://www.expedia.ca/Southbury-Hotels-Simple-Living-Retreat-1-Bedroom-Apartment.h111828646.Hotel-Information) Southbury 9.8/10 Exceptional (19) "Perfect sized apartment for a short stay - very convenient to my destination" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) S CA $124 CA $170 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Southbury-Hotels-Simple-Living-Retreat-1-Bedroom-Apartment.h111828646.Hotel-Information) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717468/7b3193ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717468/7fbb18e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717468/120892ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717468/8a733476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Local Artist Inspired | Walk to WestPoint + King Bed [](https://www.expedia.ca/Highland-Falls-Hotels-Local-Artist-Inspired-Walk-To-WestPoint-King-Bed.h94717468.Hotel-Information) Highland Falls 9.2/10 Wonderful (9) "Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jesse C. CA $124 CA $527 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Highland-Falls-Hotels-Local-Artist-Inspired-Walk-To-WestPoint-King-Bed.h94717468.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/3a9ea66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/e56d490f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/dfec5e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/c55e3667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands [](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) Fort Montgomery 9.8/10 Exceptional (129) "It has an incredible mountain and water view. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MIHYUN CA $259 CA $419 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103760000/103760000/103759987/1d63c478.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103760000/103760000/103759987/ffcdd459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/104000000/103760000/103760000/103759987/3f3ffc87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/104000000/103760000/103760000/103759987/31ccdf44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Creekside Retreat Tent [](https://www.expedia.ca/New-Milford-Hotels-Creekside-Retreat-Tent.h103759987.Hotel-Information) New Milford 10/10 Exceptional (4) "Absolutely beautiful location and wonderful hosts very romantic spot lots of hiking trails near and on premises me and my husband loved the fact we slept by the water and can hear the water running all night very peaceful and beautiful site ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) yarelis t. CA $207 CA $265 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/New-Milford-Hotels-Creekside-Retreat-Tent.h103759987.Hotel-Information) ![Free daily local cuisine breakfast](https://images.trvl-media.com/lodging/79000000/78090000/78087000/78087000/624b7f29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78090000/78087000/78087000/b61e0c9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room 6 - The George, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/79000000/78090000/78087000/78087000/733c3739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78090000/78087000/78087000/9448f66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Millbrook Inn [](https://www.expedia.ca/Millbrook-Hotels-The-Millbrook-Inn.h78087000.Hotel-Information) Millbrook 10/10 Exceptional (5) "Love it! beautiful inn and amazing food!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yasmin [](https://www.expedia.ca/Millbrook-Hotels-The-Millbrook-Inn.h78087000.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=2025-12-27&endDate=2025-12-28®ionId=183644&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Brewster Hotel Reviews ## Explore a world of travel with Expedia - Lodging - More ways to book - [Beach Hotel Hotels in Carmel ](https://www.expedia.ca/Carmel-Hotels-Beach-Hotel.0-0-d553248634998943944-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Carmel ](https://www.expedia.ca/Carmel-Hotels-Cheap-Hotels.0-0-d553248634998943944-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Carmel ](https://www.expedia.ca/Carmel-Hotels-Hotel-With-Pool.0-0-d553248634998943944-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Carmel ](https://www.expedia.ca/Carmel-Hotels-Luxury-Hotel.0-0-d553248634998943944-tLuxuryHotel.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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