Title: Book the Best Hotels with BARS in Chester in 2025 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d6046665.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d6046665.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d6046665.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d6046665.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Bar in Chester, NY from CA $151 ![](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 Chester Hotels with Bar ## Top Chester 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) ![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) ![Lobby](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/13890846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Overlook Lodge at Bear Mountain Bear Mountain 8.4/10 Very good (1018) "Clean room, easy parking" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $161 CA $183 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/e31233cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/61f4bfc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/b675c11d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/0564b8da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Crowne Plaza Suffern - Mahwah by IHG Suffern 8.8/10 Excellent (1019) "Excellent staff at a beautiful hotel" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy CA $145 CA $169 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.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) ![Outdoor pool](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/a7704166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/5555dde6.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 " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Arnassia CA $322 CA $438 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Goshen-Hotels-LEGOLAND-Hotel-NEW-York.h70415091.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/800/736/w3839h2556x0y3-9a7a26d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 8:30 AM to 9:30 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/800/736/c532560d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/800/736/13a47184.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/800/736/a3863609.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Nanuet Nanuet 8.8/10 Excellent (1008) "Staff was really friendly" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Wanda CA $160 CA $186 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.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/1000000/930000/921500/921424/9b61f0f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/60661c7b.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) ### Courtyard by Marriott Middletown Goshen Middletown 8.6/10 Excellent (1004) "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. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Angel 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) ![Lobby](https://images.trvl-media.com/lodging/1000000/480000/473500/473490/d11440c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/480000/473500/473490/3770735e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave](https://images.trvl-media.com/lodging/1000000/480000/473500/473490/f101dd2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/480000/473500/473490/c09894ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western The Inn At Ramsey Ramsey 7.2/10 Good (1015) "Clean and comfortable rooms, friendly staff and a really nice hot breakfast." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Karlyn CA $131 CA $151 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Ramsey-Hotels-Best-Western-The-Inn-At-Ramsey.h473490.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) ![Sports facility](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/2f2f704a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/459515b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Fishkill Fishkill 8.6/10 Excellent (1011) "It was a great place to stay " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda CA $150 CA $170 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.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) ![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) ![Reception](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/2a01f3da.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 " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Dirwin CA $142 CA $168 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Newburgh-Stewart-Airport.h42673.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21000/20986/2c7b4ca0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/21000/20986/e5fb47c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/21000/20986/dd17ff0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/21000/20986/96db1dd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Mahwah Mahwah 7.8/10 Good (895) "The property was everything I expected, am I will definitely be back , highly appreciative of the cleanliness, staff and set up No complaints " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Da'Quan CA $160 CA $184 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Mahwah-Hotels-DoubleTree-By-Hilton-Mahwah.h20986.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/91000000/90240000/90233900/90233861/3ea39c39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Double Room, Multiple Beds, 2 Bathrooms](https://images.trvl-media.com/lodging/91000000/90240000/90233900/90233861/9eb11a8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90240000/90233900/90233861/60761b81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/91000000/90240000/90233900/90233861/53f48deb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Orange Inn Boutique Hotel Goshen 9.6/10 Exceptional (145) "Very spacious room, friendly staff, modern touches" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristina CA $263 CA $324 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Goshen-Hotels-The-Orange-Inn-Boutique-Hotel.h90233861.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=2025-10-31&endDate=2025-11-01®ionId=6046665&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![Holiday Inn Express Hotel & Suites Chester by IHG](//images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e_y.jpg) ### Holiday Inn Express Hotel & Suites Chester by IHG 10/10 Excellent "It was a really nice stay and everything was clean and well maintained" [](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.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 "This time got very clean and spacious room. All was great!" [](https://expedia.ca/Newburgh-Hotels-The-Crossroads-Hotel.h14410.Hotel-Information) ![Hampton Inn & Suites Mahwah](//images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/c56a5aff_y.jpg) ### Hampton Inn & Suites Mahwah 10/10 Excellent "Close EV charging and parking. Staff was friendly and helpful." [](https://expedia.ca/Mahwah-Hotels-Hampton-Inn-Suites-Mahwah.h3555820.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) ![Crowne Plaza Suffern - Mahwah by IHG](//images.trvl-media.com/lodging/1000000/10000/2400/2358/e31233cf_y.jpg) ### Crowne Plaza Suffern - Mahwah by IHG 10/10 Excellent "Marvellous stay at this wonderfully equipped, convenient hotel. Front desk staff were delightful (shout out to Yvonne!), friendly as well as competent and efficient. Infinitely more suitable for our business trip than the weird and wanting airbnb options we have tried in the area. Thank you, Crown Plaza!" [](https://expedia.ca/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.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) ![DoubleTree by Hilton Mahwah](//images.trvl-media.com/lodging/1000000/30000/21000/20986/2c7b4ca0_y.jpg) ### DoubleTree by Hilton Mahwah 10/10 Excellent "The property was everything I expected, am I will definitely be back , highly appreciative of the cleanliness, staff and set up No complaints " [](https://expedia.ca/Mahwah-Hotels-DoubleTree-By-Hilton-Mahwah.h20986.Hotel-Information) ![Extended Stay America Suites Ramsey Upper Saddle River](//images.trvl-media.com/lodging/1000000/870000/867400/867313/99577371_y.jpg) ### Extended Stay America Suites Ramsey Upper Saddle River 10/10 Excellent "Happy Happy :-)" [](https://expedia.ca/Ramsey-Hotels-Extended-Stay-America-Suites-Ramsey-Upper-Saddle-River.h867313.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Chester? > Though you might not find a hotel in Chester well-known for its bar, you will find 19 properties to choose from, some of which will have an onsite bar where you can unwind with a late-night cocktail after sightseeing. While you're in the area, consider a visit to LEGOLAND® New York and Woodbury Common Premium Outlets. ### What are the best hotels with bars in Chester? > Here are a few of the top hotels with bars in and around Chester: [Holiday Inn Express Hotel & Suites Chester by IHG](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. [Sonesta Simply Suites Nanuet](https://www.expedia.ca/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information): Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. [Hampton Inn Nanuet](https://www.expedia.ca/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. [Overlook Lodge at Bear Mountain](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. ### What is there to do in Chester? > If you have time to explore, consider visiting LEGOLAND® New York, Woodbury Common Premium Outlets, and Castle Fun Center, and then find a cozy spot for a nightcap. Other places to see include The Rock Sports Complex and Museum Village. Chester is appreciated for its shops and restaurants. ### When is the best time to visit Chester? > Visiting local bars in Chester is more fun when you know what the weather holds. These rainfall averages and temperatures can help you choose the best time for bar hopping. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Chester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall. ### How can I get to Chester and around the area? > You might want to make the most of these transportation choices in and around Chester: Fly into Stewart Intl. Airport (SWF), which is located 13.5 mi (21.7 km) away from the heart of the city. You can also search for flights into Caldwell, NJ (CDW-Essex County), which is 33.6 mi (54.1 km) away. 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