Title: Book the Best Montgomery WINERY Hotels in 2025 | Expedia.ca [Hotels in Montgomery](https://expedia.ca/Montgomery-Hotels.d8728.Travel-Guide-Hotels)[Vacation Rentals in Montgomery](https://expedia.ca/Montgomery-Vacation-Rentals.d8728.Travel-Guide-VacationRentals)[Things to do in Montgomery](https://expedia.ca/Things-To-Do-In-Montgomery.d8728.Travel-Guide-Activities)[Montgomery Car Rentals](https://expedia.ca/Car-Rentals-In-Montgomery.d8728.Car-Rental-Guide)[Montgomery Vacation Packages](https://expedia.ca/Montgomery.d8728.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/7258650cf3c9c107b2e4d18aa267cfe2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by ViajandoconAna Rustrian # Find Winery Hotels in Montgomery, NY from CA $156 ![](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 Montgomery Winery Hotels Tonight [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-10-11&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Montgomery Winery Hotels ![Exterior](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/98944f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/fe354234.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/f3b7bb7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/dc5981dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Montgomery by IHG Montgomery 8.8/10 Excellent (767) "We really like the hotel and area very safe" CA $133 CA $156 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/47637293.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/25051ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/49ef52ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hanlon Suite | Children's theme room](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/05c3d7b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borland House Inn Montgomery 9.2/10 Wonderful (130) "Unique experience, very comfortable, clean and quaint" CA $144 CA $162 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/105000000/104970000/104965400/104965399/feb0c593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/105000000/104970000/104965400/104965399/c01759b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/105000000/104970000/104965400/104965399/217d0423.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/105000000/104970000/104965400/104965399/d8180870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Hudson Valley Apt 202 - King/Queen/Twin Montgomery 9.8/10 Exceptional (12) "Such a cute apartment and very clean. Everything is new and the town is very quaint!! Close to other things like shopping and restaurants. Definitely would stay again and recommend to anyone looking for a clean, quiet and safe area to stay." CA $213 CA $397 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Montgomery-Hotels-Modern-Hudson-Valley-Apt-202-KingQueenTwin.h104965399.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99760000/99751300/99751209/7ce217c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/100000000/99760000/99751300/99751209/4246803e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99760000/99751300/99751209/26c38d83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99760000/99751300/99751209/33d9a952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Farmhouse-Hot Tub, King Beds, Game Room & View Montgomery 10/10 Exceptional (15) "We loved our stay here! The property is gorgeous and the hosts were helpful and communicative. The house was clean and had everything we needed." CA $828 CA $1,581 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Montgomery-Hotels-Dream-Escape.h99751209.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) ![Reception](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/dab27d3b.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) ![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 New Paltz 9.4/10 Exceptional (1009) "Good breakfast, quiet and clean nice place" CA $171 CA $192 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/ecb80f49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bars/lounges](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/90312aff.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) ![Concierge desk](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/e3c7f442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Resorts World Catskills Casino Monticello 8.6/10 Excellent (1080) "Great place to stay" CA $205 CA $267 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/7472348e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/130ec357.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/4ae12198.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Accessible (Hearing)](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/4eb66254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites By Hilton Poughkeepsie Poughkeepsie 9.4/10 Exceptional (348) "Great stay" CA $160 CA $185 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Poughkeepsie-Hotels-Home2-Suites-By-Hilton-Poughkeepsie.h103394153.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/dc93786c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/1765b81e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/a90c96fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Poughkeepsie Poughkeepsie 8.8/10 Excellent (1005) "Clean room, staff is friendly especially at the cafe. " CA $154 CA $174 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/e1e7e350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/2831de3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/239951b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/2f2f704a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Fishkill Fishkill 8.6/10 Excellent (1003) "It was a great place to stay " CA $167 CA $189 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/3df08b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/11f1915d.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/18000000/17270000/17262200/17262186/e34f60f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/275854de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Newburgh Stewart Airport Newburgh 9.2/10 Wonderful (952) "Nice place to stay! " CA $194 CA $229 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-Suites-Newburgh-Stewart-Airport.h17262186.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=2025-10-25&endDate=2025-10-26®ionId=8728&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Montgomery Hotel Reviews ![Quality Inn & Suites Fishkill South near I-84](//images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/12805cb0_y.jpg) ### Quality Inn & Suites Fishkill South near I-84 10/10 Excellent "Spacious Bathroom " [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Suites-Fishkill-South-Near-I-84.h1766609.Hotel-Information) ![Hampton Inn Harriman Woodbury](//images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Found this hotel last year, it is super convenient for getting to the NY ren faire and has a Popeye's just up the driveway plus a whole shopping complex but you would never know when you are at the hotel. It is tucked all the way in the back and is nice & quiet. " [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Hampton Inn & Suites Poughkeepsie](//images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "The room was very large and the price was great." [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Holiday Inn Express Poughkeepsie by IHG](//images.trvl-media.com/lodging/1000000/20000/12200/12157/9d729415_y.jpg) ### Holiday Inn Express Poughkeepsie by IHG 10/10 Excellent "Good stay. Nothing really special about the place except the breakfast which had more choices than usual." [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.Hotel-Information) ![Americas Best Value Inn New Paltz](//images.trvl-media.com/lodging/1000000/900000/897900/897882/1c07aec9_y.jpg) ### Americas Best Value Inn New Paltz 10/10 Excellent "When it comes to a pleasant surprise, this was definitely IT! Clean, comfortable, inexpensive, friendly, renovated, and (did I mention) inexpensive!?? Adorable little breakfast area with complimentary breakfast foods as well. " [](https://expedia.ca/Poughkeepsie-Hotels-Americas-Best-Value-Inn-New-Paltz.h897882.Hotel-Information) ![Super 8 by Wyndham Montgomery Maybrook](//images.trvl-media.com/lodging/1000000/860000/855600/855538/7ac7ec53_y.jpg) ### Super 8 by Wyndham Montgomery Maybrook 6/10 Okay "Staff Registration person excellent. Aged property-Some furniture needs replacement. Clean bed and bathroom. Typical Super 8 property. Close to I 84. EZ off and on." 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