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Find Hotels with Bar in Chester, NY from CA $153

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Check availability on Chester Hotels with Bar

Tonight
Oct 2 - Oct 3
Tomorrow
Oct 3 - Oct 4
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Chester hotels with a bar

A landscaped outdoor area with a fire feature, seating, and a pathway.
A Courtyard by Marriott hotel with a sign, parking, and landscaped flower beds.
A modern hotel lobby with a seating area, large windows, and a television screen.
A modern hotel lobby with a fireplace, comfortable seating, and a television.

1. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
Middletown
United States
john
CA $144
CA $170 total
includes taxes & fees
Oct 28 - Oct 29
Courtyard by Marriott Middletown Goshen
A swimming pool with colorful umbrellas and lounge chairs.
A hotel room with a large bed, a bookshelf, a mural, and a window with curtains.
A bar area with a long counter, multiple hanging lights, and a variety of bottles.
A colorful play area with a check-in counter and a mascot.

2. LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
Goshen
United States
Kylaia
CA $154
CA $369 total
includes taxes & fees
Oct 4 - Oct 5
LEGOLAND Hotel NEW York
A brick exterior with outdoor seating, tables covered with white tablecloths, and brick walls.
A lobby with green and blue upholstered chairs, a Christmas tree, and a bar area with red bar stools.
A hotel room with a large bed, a desk, a chair, and a TV.
A cozy lounge area with green and blue upholstered chairs, marble tables, and a fireplace.

3. The Orange Inn Boutique Hotel

The Orange Inn Boutique Hotel
Goshen
United States
DENISE
CA $329
CA $405 total
includes taxes & fees
Oct 8 - Oct 9
The Orange Inn Boutique Hotel
An outdoor patio with a dining table and chairs, a barbecue grill, and a fire pit.
A spacious lobby with modern seating, a stone accent wall, and large windows offering views.
An indoor swimming pool with clear water, surrounded by grey tiled flooring and walls, large windows offering views of the outside, and a lifeguard station with a ladder.
A modern bar area with a stone accent wall, a long wooden bar counter, and a flat-screen TV mounted above the bar.

4. Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen
Middletown
United States
jubert cruz
CA $268
CA $316 total
includes taxes & fees
Nov 1 - Nov 2
Residence Inn by Marriott Middletown Goshen
A spacious dining area with multiple tables and chairs, a stone wall with a mounted deer head, and a fireplace.
A wooden reception desk with a man standing behind it, a staircase, and a wooden interior.
A large, multi-story stone building with a prominent arched entrance and multiple windows.
A large outdoor swimming pool surrounded by trees and a covered pavilion.

5. Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
Bear Mountain
United States
randall
CA $124
CA $153 total
includes taxes & fees
Nov 3 - Nov 4
Overlook Lodge at Bear Mountain
A Courtyard Marriott hotel with a covered entrance, outdoor seating area, and multiple balconies.
A modern hotel room with a flat-screen TV, a desk with drawers, a comfortable sofa, a bed, and a large window with curtains.
A modern living room with a sectional sofa, two armchairs, a coffee table, and a TV.
An outdoor patio area with wicker furniture and a stone wall.

6. Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport
Newburgh
United States
John
CA $205
CA $242 total
includes taxes & fees
Oct 4 - Oct 5
Courtyard by Marriott Newburgh Stewart Airport
A spacious lobby with a high ceiling, wooden beams, a central green wall with plants, seating areas, and a bar.
A spacious atrium with a central water feature, multiple seating areas, and a bar.
A spacious indoor area with multiple seating arrangements, including sofas and round tables, and a central decorative table with flowers.
A modern lobby with a fireplace, four armchairs, a coffee table, and a desk with a computer.

7. Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG
Suffern
United States
mary
CA $174
CA $202 total
includes taxes & fees
Oct 6 - Oct 7
Crowne Plaza Suffern - Mahwah by IHG
A modern bedroom with a four-poster bed, a desk, and a chair.
A kitchen with a stainless steel sink, a coffee maker, a bottle of hand soap, a paper towel dispenser, and a microwave.
A staircase with a black handrail and a fire alarm on the wall.
A multi-story brick building with storefronts on the ground floor.

8. Columbus Hotel

Columbus Hotel
Middletown
United States
Joseph
CA $147
CA $271 total
includes taxes & fees
Oct 4 - Oct 5
Columbus Hotel
A dining area with brick flooring, large arched windows, and outdoor seating visible through the windows.
A large, two-story house with a covered patio area and a well-maintained lawn.
A dining area with a fireplace, white tablecloths, and a variety of decorative plates on the walls.
A cozy living room with a fireplace, wooden paneling, a patterned rug, and a dining area with a chandelier.

9. Stagecoach Inn

Stagecoach Inn
Goshen
United States
Kathryn
CA $532
CA $655 total
includes taxes & fees
Oct 15 - Oct 16
Stagecoach Inn
A spacious lobby with a modern design, featuring a seating area with sofas and armchairs, a decorative wall panel, and a large window providing natural light.
A hotel lobby with a reception desk, seating area, and a large window allowing natural light.
A modern restaurant interior with a bar area, seating, and a dessert display.
A hotel room with a large bed, a bedside table with a lamp, a TV, and a bathroom with a mirror and sink.

10. DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
Nanuet
United States
Linda
CA $185
CA $216 total
includes taxes & fees
Nov 2 - Nov 3
DoubleTree by Hilton Hotel Nanuet
View all properties

Top Chester Hotel Reviews

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"The hotel was great. The only problem was there is an internal bar that was supposed to close at 11:00 pm but there was a lot of noise from the bar until after midnight."
Douglas 2-night trip
Posted 10 hours ago
Crowne Plaza Suffern - Mahwah by IHG
The Thayer Hotel at West Point

The Thayer Hotel at West Point

10/10 Excellent
"Everything was great, and really added a special feeling to the trip"
Joshua 1-night trip
Posted 11 hours ago
The Thayer Hotel at West Point
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"Friendly staff, quick check in, easy parking. Room was clean and comfortable. Easy access to Bear Mountain. Nice restaurant. No elevator in Overlook Lodge so a few trips required to bring luggage upstairs."
Mary 1-night trip
Posted 2 days ago
Overlook Lodge at Bear Mountain
Hilton Garden Inn Nanuet

Hilton Garden Inn Nanuet

10/10 Excellent
"Great stay"
Danny 1-night trip
Posted 3 days ago
Hilton Garden Inn Nanuet
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

8/10 Good
"Nice hotel, needs a little updating."
Geraldine 2-night trip
Posted 7 days ago
DoubleTree by Hilton Hotel Nanuet

Frequently asked questions

Searching for hotels with bars in Chester?
Chester offers 21 properties to choose from, and likely many will have a bar where you can enjoy an evening cocktail after sightseeing. While you're in the area, consider visiting 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: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Overlook Lodge at Bear Mountain: Hotel with restaurant. Enjoy the 2 bars, free WiFi, and breakfast. Sleep Inn & Suites Middletown - Goshen: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. Crowne Plaza Suffern - Mahwah by IHG: Enjoy the bar, free WiFi, and free parking. La Quinta Inn & Suites by Wyndham Middletown-Goshen: 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 Woodbury Common Premium Outlets, Castle Fun Center, and Museum Village, and then find a cozy spot for a nightcap. Other places to see include The Rock Sports Complex and Goosepond Mountain State Park. 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. If you'd like to explore around the area, consider renting a car to take in more sights.

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