Title: Book the Best Hotels with BARS in Montgomery 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 Hotels with Bar in Montgomery, NY from CA $161 ![](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 Hotels with Bar ## Top Montgomery Hotels with Bar ![Restaurant](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/383ffb6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/13890846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Non Smoking (Stone Cottages at Bear Mountain)](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/42067525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Overlook Lodge at Bear Mountain Bear Mountain 8.4/10 Very good (1014) "Clean room, easy parking" CA $145 CA $165 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/9bb388bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/f1893b0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/c1f101cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/28ad5864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Poughkeepsie / Hudson Valley Crown Heights 8.8/10 Excellent (1009) "Great place to stay " CA $166 CA $192 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hyatt-Place-Poughkeepsie.h37960419.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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/a90c96fc.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) ![Living area](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/dc93786c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Poughkeepsie Poughkeepsie 8.8/10 Excellent (1011) "Clean room, staff is friendly especially at the cafe. " CA $154 CA $175 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.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) ![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) ![Concierge desk](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/e3c7f442.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 (1088) "I went on a family trip and had a really great time. " CA $206 CA $268 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.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) ![Children's play area - indoor](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/9834d0ca.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) ### LEGOLAND Hotel NEW York Goshen 8.6/10 Excellent (11) "We loved everything from the staff to the stay " CA $321 CA $438 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Goshen-Hotels-LEGOLAND-Hotel-NEW-York.h70415091.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/acc87956.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/875b6b8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/025b23c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Mountain View | Living area](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/78e69393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Poughkeepsie Convention Center Downtown Poughkeepsie 8.4/10 Very good (1016) "Over all it is a nice hotel to stay." CA $154 CA $181 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information) ![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/1000000/930000/921500/921424/046baaca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/bacb5b9b.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) ### Courtyard by Marriott Middletown Goshen Middletown 8.6/10 Excellent (1001) "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. " CA $136 CA $161 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![Premium bedding, down comforters, in-room safe, laptop workspace](https://images.trvl-media.com/lodging/105000000/104100000/104096900/104096853/8d195da7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed (Heartwood)](https://images.trvl-media.com/lodging/105000000/104100000/104096900/104096853/c4dc468a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Heartwood)](https://images.trvl-media.com/lodging/105000000/104100000/104096900/104096853/b95154c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/105000000/104100000/104096900/104096853/8ab8e144.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Heartwood Arlington 9.8/10 Exceptional (205) "Beautiful hotel, friendly and helpful staff, great experience all around " CA $219 CA $255 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Poughkeepsie-Hotels-The-Heartwood.h104096853.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/7494afa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 6 AM to 11 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/9b9c3b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/2a01f3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/b3546f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Newburgh Stewart Airport Newburgh 8.2/10 Very good (685) "Property clean rooms clean front desk the Best " CA $142 CA $167 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Newburgh-Stewart-Airport.h42673.Hotel-Information) ![7 bars/lounges](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/9db559da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/a57b1b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, steam room, body treatments](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/af635e5a.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/101000000/101000000/100997000/100996967/1bb15d19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Alder at Resorts World Catskills Monticello 8.2/10 Very good (182) "Great place to stay " CA $150 CA $205 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Monticello-Hotels-The-Alder-At-Resorts-World-Catskills.h100996967.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=2025-10-28&endDate=2025-10-29®ionId=8728&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Montgomery Hotel Reviews ![The Crossroads Hotel, Newburgh](//images.trvl-media.com/lodging/1000000/20000/14500/14410/5440914b_y.jpg) ### The Crossroads Hotel, Newburgh 10/10 Excellent "Yes " [](https://expedia.ca/Newburgh-Hotels-The-Crossroads-Hotel.h14410.Hotel-Information) ![DoubleTree by Hilton Poughkeepsie Convention Center](//images.trvl-media.com/lodging/1000000/20000/14600/14563/acc87956_y.jpg) ### DoubleTree by Hilton Poughkeepsie Convention Center 10/10 Excellent "The parking garage needs a little more lighting at night. The ice machine on the 10th floor did not seem to be working so I ventured to the 8th floor for ice. Would be nice to have hook on the back of the bathroom door. liked that there was bottled water in my room." [](https://expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information) ![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 "Great " [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Suites-Fishkill-South-Near-I-84.h1766609.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 "Clean comfortable room. Bed was very comfortable. Hotel was quiet " [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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 staff were extraordinary. From the moment we arrived to the moment we departed they were friendly, attentive to our needs and helpful with suggestions for a local restaurant that we could walk to (excellent Peruvian food!), to pouting out the freshly baked cookies and refreshed coffee and tea in the afternoon (we would have walked right past and the "pick me up" was just what we needed after a long day of travel. Claire, who works the evening shift, was especially helpful. Our room was clean and quiet although the bathroom was a bit dated. All in all we were delighted." [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](//images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 10/10 Excellent "Great Views, very convenient " [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Hampton Inn by Hilton New Paltz](//images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb_y.jpg) ### Hampton Inn by Hilton New Paltz 10/10 Excellent "Friendly, attentive staff. Prompt service. Room in perfect condition. Climate control great. " [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![Ramada by Wyndham Newburgh/West Point](//images.trvl-media.com/lodging/1000000/20000/11400/11304/98af6d38_y.jpg) ### Ramada by Wyndham Newburgh/West Point 10/10 Excellent "Parking, easy checking in " [](https://expedia.ca/Newburgh-Hotels-Ramada-By-Wyndham-NewburghWest-Point.h11304.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Montgomery? > Montgomery features 22 properties to choose from, and likely many will have a bar where you can unwind with a late-night cocktail. While you're in the area, you can check out LEGOLAND® New York and Woodbury Common Premium Outlets. ### What are the best hotels with bars in Montgomery? > Below are some of top hotels with bars in and around Montgomery: [Super 8 by Wyndham Montgomery Maybrook](https://www.expedia.ca/Newburgh-Hotels-Super-8-By-Wyndham-Montgomery-Maybrook.h855538.Hotel-Information): Hotel with 5 restaurants. Enjoy the 2 bars, water park, and breakfast. [Holiday Inn Express & Suites Montgomery by IHG](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information): Hotel with 6 restaurants. Enjoy the 6 bars, full-service spa, and casino. [The Kartrite Resort & Indoor Waterpark](https://www.expedia.ca/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information): Resort with restaurant. Enjoy the 3 bars, free WiFi, and free parking. [Quality Inn Poughkeepsie](https://www.expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Poughkeepsie.h6465.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. [Resorts World Catskills Casino](https://www.expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. ### What is there to do in Montgomery? > In the area, you can visit LEGOLAND® New York, Woodbury Common Premium Outlets, and Orange County Arboretum, then find a cozy spot for a nightcap. Other places to see include City Winery Hudson Valley and Highland Lakes State Park. Montgomery is appreciated for its restaurants. ### When is the best time to visit Montgomery? > Visiting local bars in Montgomery is more fun when you know what the weather holds. These temperatures and rainfall averages can help you decide the best time for bar hopping. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Montgomery are January, February, March, and April, with each month seeing an average of 6 inches of snowfall. ### How can I get to Montgomery and around the area? > You might want to make the most of these transportation choices in and around Montgomery: Fly into Stewart Intl. Airport (SWF), which is located 8 mi (12.9 km) away from the city center. 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