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 $162 ![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 Montgomery Hotels with Bar ## Top Montgomery Hotels with Bar ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/47637293.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) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/91f0a8ce.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) ### Borland House Inn Montgomery 9.2/10 Wonderful (128) "Unique experience, very comfortable, clean and quaint" CA $143 CA $162 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.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=2025-10-17&endDate=2025-10-18®ionId=8728&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Montgomery Hotel Reviews ![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 "This place has one of the best showers! The water pressure is almost like getting power washed. My husband loved it! Convient to Main St Poughkeepsie for dining options." [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.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 "T" [](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 staff, clean rooms. Could use better seating." [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.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 spacious, clean, and comfortable. There is direct TV available for entertainment. Breakfast was nice. The presence of a pool and hot tub is great too. This hotel accepts dogs and cats 50 lbs and under with additional fee." [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.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 "This hotel was wonderful. We attended a concert at the Civic Center and staying here was so convenient. Very clean, friendly staff, " [](https://expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information) ![Quality Inn Poughkeepsie](//images.trvl-media.com/lodging/1000000/10000/6500/6465/a647c710_y.jpg) ### Quality Inn Poughkeepsie 10/10 Excellent "Really wonderful staff." [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Poughkeepsie.h6465.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 "Great natural setting. Comprehensive facilities." [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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 "Convenient, great parking, quiet, comfortable room with a friendly staff." [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Suites-Fishkill-South-Near-I-84.h1766609.Hotel-Information) ![The Crossroads Hotel, Newburgh](//images.trvl-media.com/lodging/1000000/20000/14500/14410/5440914b_y.jpg) ### The Crossroads Hotel, Newburgh 10/10 Excellent "The staff was efficient. The rooms were clean the common areas i.e. hallways need to be updated and repaired. The hotel is very quiet. The rooms are nice. I’d stay here again." [](https://expedia.ca/Newburgh-Hotels-The-Crossroads-Hotel.h14410.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Montgomery? > Montgomery features 23 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. [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. [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. ### 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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