Title: Book the Best Montgomery WINERY Hotels in 2026 | 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) ![Autumn foliage in the Mohawk Valley, Montgomery County, New York State, USA.](https://images.trvl-media.com/place/8728/e92a028d-f2c6-4a41-a280-7692010fed7a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/8728/e92a028d-f2c6-4a41-a280-7692010fed7a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Jan 28 - Jan 29](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2026-01-28&endDate=2026-01-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 29 - Jan 30](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2026-01-29&endDate=2026-01-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Montgomery hotels with winery ![Exterior](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/98944f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/605b2de6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/4856168e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/abf8ab38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Montgomery by IHG [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) Montgomery 8.8/10 Excellent (819 reviews) "The staff was great! The room was clean and the breakfast was excellent." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Joey CA $112 CA $127 total includes taxes & fees Feb 8 - Feb 9 [](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) ![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) ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/00e54810.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/20894557.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borland House Inn [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) Montgomery 9.2/10 Wonderful (147 reviews) "Breakfast was hot and tasty. Staff were all pleasant and accommodating. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) wendy [](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) ![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) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/105000000/104970000/104965400/104965399/3424405a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Hudson Valley Apt 202 - King/Queen/Twin [](https://www.expedia.ca/Montgomery-Hotels-Modern-Hudson-Valley-Apt-202-KingQueenTwin.h104965399.Hotel-Information) Montgomery 9.8/10 Exceptional (16 reviews) "We had a great stay!! I booked for a “get ready” spot for my wedding and it was everything I could have dreamed of. Everything was perfect and very clean! Can’t wait to book again Very centrally located near some amazing small boutiques, a couple restaurants. The town seemed like a popular spot on the weekend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tiffani H. CA $205 CA $370 total includes taxes & fees Jan 29 - Jan 30 [](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/100000000/99760000/99751300/99751209/37d2f11c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/100000000/99760000/99751300/99751209/7a8f89cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/100000000/99760000/99751300/99751209/20dd4d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/100000000/99760000/99751300/99751209/511279ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Farmhouse-Hot Tub, King Beds, Game Room & View [](https://www.expedia.ca/Montgomery-Hotels-Dream-Escape.h99751209.Hotel-Information) Montgomery 10/10 Exceptional (15 reviews) "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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily B. CA $990 CA $1,759 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Montgomery-Hotels-Dream-Escape.h99751209.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/111000000/110300000/110297600/110297545/7ce1352f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110300000/110297600/110297545/e358b978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/111000000/110300000/110297600/110297545/a69379da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/111000000/110300000/110297600/110297545/c1748f32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites Central Valley - Woodbury [](https://www.expedia.ca/Central-Valley-Hotels-Comfort-Suites-Central-Valley-Woodbury.h110297545.Hotel-Information) Central Valley 10/10 Exceptional (4 reviews) "Close to town, restaurants, gas, etc… Very clean, comfy bed, decent breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $127 CA $156 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Central-Valley-Hotels-Comfort-Suites-Central-Valley-Woodbury.h110297545.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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/9a6a049d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/833333a3.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) ### Courtyard by Marriott Poughkeepsie [](https://www.expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) Poughkeepsie 8.8/10 Excellent (1,020 reviews) "The room was clean and the staff was amazing! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tara CA $121 CA $137 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.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) ![55-inch LED TV with satellite channels, streaming services](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/cc7999bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/693279c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/c695ef3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites By Hilton Poughkeepsie [](https://www.expedia.ca/Poughkeepsie-Hotels-Home2-Suites-By-Hilton-Poughkeepsie.h103394153.Hotel-Information) Poughkeepsie 9.4/10 Exceptional (405 reviews) "Rooms were clean, staff was friendly and breakfast was good." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carole CA $140 CA $163 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Poughkeepsie-Hotels-Home2-Suites-By-Hilton-Poughkeepsie.h103394153.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/dab27d3b.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) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/00367844.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 (1,001 reviews) "Excellent service, clean rooms " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rafeena CA $166 CA $186 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.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/e1e7e350.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/f4de9a4d.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 (1,008 reviews) "Room was clean,Staff was very friendly and helpful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Antonio CA $125 CA $141 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.Hotel-Information) ![Resort view](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/0479130a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/d6b9765c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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) ### Resorts World Catskills Casino [](https://www.expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information) Monticello 8.8/10 Excellent (1,114 reviews) "Yessss the hotel was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelvin [](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=2026-02-11&endDate=2026-02-12®ionId=8728&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Montgomery Hotel Reviews ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "Everything was great . " [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg) ### Courtyard by Marriott Poughkeepsie 10/10 Excellent "Friendly staff and updated & very clean room" [](https://expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.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 "Very kind and courteous staff, very clean rooms. " [](https://expedia.ca/Poughkeepsie-Hotels-Americas-Best-Value-Inn-New-Paltz.h897882.Hotel-Information) ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "An amazing experience - the staff was excellent" [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Super 8 by Wyndham Montgomery Maybrook](https://images.trvl-media.com/lodging/1000000/860000/855600/855538/7ac7ec53_y.jpg) ### Super 8 by Wyndham Montgomery Maybrook 10/10 Excellent "Nice place" [](https://expedia.ca/Newburgh-Hotels-Super-8-By-Wyndham-Montgomery-Maybrook.h855538.Hotel-Information) ## Frequently asked questions ### How much does a winery hotel in Montgomery cost? ### Which are the top Montgomery winery hotels for couples? > The 3-star Borland House Inn boasts a lovely guest rating of 9.2, making it a delightful choice for a romantic getaway. This historic inn offers free full breakfast, ensuring you start your day off right. It's conveniently located near local wineries, great for couples looking to enjoy wine tours together. The inn also features beautiful accommodations and is known for its friendly staff, setting a friendly setting for a relaxing retreat. ### Which area of Montgomery is best to stay in for vineyards and wineries? > For couples looking for a romantic escape, the nearby wineries offer intimate experiences great for special moments. Many vineyards provide outdoor seating with breathtaking views, ideal for sharing a bottle of wine as the sun sets over the valley. You might even consider booking a vineyard tour or a wine and cheese pairing experience to enhance your getaway. > > > Families will appreciate the welcoming atmosphere of Montgomery, where some wineries offer kid-friendly activities and spaces. With picnic areas and scenic trails, it's easy to spend a day enjoying the outdoors while the adults partake in tastings. The combination of family-friendly fun and the beauty of the vineyards makes for a memorable trip for all ages. ### Are there hotels in Montgomery near winery tours? > The 3-star Borland House Inn boasts a fantastic review score of 9.2 and is known for its beautiful house and friendly staff. It offers complimentary breakfast and free Wi-Fi, making it a comfortable and welcoming base for couples. Plus, it's conveniently located near winery tours, so you can easily explore the local vineyards. > > > Another great option is the Holiday Inn Express & Suites Montgomery, which has a solid review rating of 8.8\. This hotel features modern and comfortable rooms, excellent service, and a complimentary breakfast. ### What winery activities should we do in Montgomery? > For couples seeking a romantic day out, the nearby Brotherhood Winery is a must-visit. Established in 1839, it is the oldest continuously operating winery in the United States. Here, you can enjoy intimate tastings in their historic cellars, followed by a leisurely stroll through the beautiful grounds. The winery often hosts special events, such as wine and cheese pairings, superb for creating memorable moments together. > > > Families will find the scenic tasting rooms at the Clearview Vineyard particularly enjoyable. With its family-friendly atmosphere, kids can explore the outdoor spaces while adults savour the award-winning wines. The vineyard also offers picnic areas, making it a great spot for a relaxing afternoon surrounded by nature. > > > Adventurous souls should not miss the opportunity to participate in vineyard tours that often include behind-the-scenes insights into the winemaking process. Many local wineries, like the Benmarl Winery, offer vineyard hikes that lead to breathtaking views of the Hudson River, making for an exhilarating experience. ### Does Montgomery host any wine festivals or events? > For couples seeking a romantic outing, these festivals offer a wonderful opportunity to enjoy the scenic beauty of the Hudson Valley while sampling exquisite wines. Strolling through the festival grounds, hand in hand with a glass of local vintage, can create unforgettable memories. > > > Families can also join in the festivities, as many events include activities for children, making it a fun day out for all ages. With food trucks, craft vendors, and interactive experiences, everyone can enjoy the lively option while exploring the local culture. ### How can I save on a winery hotel in Montgomery with Expedia? ### Is it cheaper to book flights and a winery hotel in Montgomery as a package deal? ### Can I cancel my winery hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Blooming Grove ](https://www.expedia.ca/Blooming-Grove-Hotels-Cheap-Hotels.0-0-d3000448042-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Blooming Grove ](https://www.expedia.ca/Blooming-Grove-Hotels-Hotels-With-Free-Breakfast.0-0-d3000448042-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Campbell Hall ](https://www.expedia.ca/Campbell-Hall-Hotels-Cheap-Hotels.0-0-d6338665-tCheapHotels.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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