A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

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Check availability on Chester Hotels with a Bar

Tonight
29 Sept - 30 Sept
Tomorrow
30 Sept - 1 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Chester hotels with a bar

A well-maintained garden with a variety of plants and flowers, a wooden pergola, and a gravel path.
A bedroom with a bed, a bedside table, a lamp, a mirror, a dresser, a window, and a ceiling fan.
A cozy living room with a stone fireplace, a leather sofa set, a wooden coffee table, and a patterned rug.
A variety of dishes including a steak, muffins, and a dessert with fruit.

1. Fullerton Inn

Fullerton Inn
Chester Depot
United States
Lisa
₹15,262
₹16,636 total
includes taxes & fees
18 Oct - 19 Oct
Fullerton Inn
A restaurant with wooden tables and chairs, a central table with a sign reading "The Red Slate Restaurant", and large windows with views of the outside.
A bar area with a sign reading "MAGIC" and "featured Vermont beers".
A hotel room with a large bathtub, a bed with a colorful quilt, two bedside lamps, and a framed picture on the wall.
A Christmas tree decorated with lights, ornaments, and a bow.

2. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Terry
₹8,902
₹10,192 total
includes taxes & fees
28 Oct - 29 Oct
The Upper Pass Lodge at Magic Mountain
A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.
An indoor swimming pool with four chairs and a hot tub.
A spacious lobby with a fireplace, leather seating, and a chandelier.
A kitchen with wooden cabinets, a white microwave, a stove, and a refrigerator.

3. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
Cristian
₹14,145
₹16,125 total
includes taxes & fees
21 Oct - 22 Oct
Pointe at Castle Hill Resort
A rustic dining area with wooden beams, tables, chairs, and a fireplace.
An outdoor event space with tables set for dining, surrounded by a covered area with a transparent roof.
A large, multi-story building with a symmetrical facade, multiple chimneys, and a well-maintained garden with evergreen trees.
A bedroom with a large bed, a bedside table, a lamp, and a view of the outdoors through a sliding door.

4. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Rula
₹22,351
₹27,895 total
includes taxes & fees
30 Sept - 1 Oct
The Inn at Weathersfield
A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.
A hotel with a swimming pool area, including two hot tubs and lounge chairs.
A balcony with a stone wall and wooden railing overlooking a grassy area with a building in the background.
A hot tub with a tiled interior and a window in the background.

5. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
United States
Daniel
₹15,834
₹19,238 total
includes taxes & fees
30 Sept - 1 Oct
Jackson Gore Village, A Vail Resorts Property
A cozy room with a fireplace, green sofas, a pool table, and a lamp.
A deck with white railings overlooking a forested area and a mountain in the distance.
A wooden interior with a dining table set for four, a wooden cabinet with glass doors, and a kitchen area with a refrigerator and cabinets.
A bedroom with a wooden floor, a bed with a white bedspread, a nightstand with a lamp, a dresser, and a television on the dresser.

6. Bromley View Inn

Bromley View Inn
Bondville
Canada
William
₹8,447
₹9,291 total
includes taxes & fees
30 Sept - 1 Oct
Bromley View Inn
A hotel room with two beds, a window with blinds, a desk with a television, and a lamp.
A reception desk with a wooden finish, a small plant, and a seating area with tables and chairs.
A stone wall surrounding a swimming pool with a metal handrail.
A lobby with a leather sofa, a television mounted on the wall, a painting, and a security control panel.

7. The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
Stratton
United States
DENNIS
₹13,060
₹15,803 total
includes taxes & fees
30 Sept - 1 Oct
The Black Bear Lodge at Stratton Mountain Resort
A large stone building with a steep roof, surrounded by dense forest and hills.
A traditional bedroom with a four-poster bed, two armchairs, a wooden wardrobe, and a mirror.
A spacious living room with a fireplace, comfortable seating, and a large window providing natural light.
A hotel room with a bed, a nightstand, a lamp, a door, and a view into another room with a couch and a window.

8. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Brandon
₹22,989
₹25,058 total
includes taxes & fees
20 Oct - 21 Oct
Castle Hill Resort And Spa
A two-story house with a red exterior and white trim. There are three large windows on the front and a chimney on the right side.
A cozy living room with a fireplace, wooden furniture, and large windows.
A spacious living room with wooden beams, a patterned sofa, a yellow armchair, and a red door.
A house with a red exterior, large windows, and a well-maintained garden with various plants and flowers.

9. COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
Weston
United States
Raedene
₹22,250
₹24,252 total
includes taxes & fees
30 Sept - 1 Oct
COHO Inn & Motor Lodge
A cozy living room with a fireplace, leather furniture, and a coffee table with a puzzle.
A cozy room with a large bed, a fireplace, and a brick wall.
A banquet hall with multiple round tables set for dining, featuring chandeliers and brick walls.
A metal bucket with a spoon, two wine glasses, and a checkered cloth on a brick ledge by a pool.

10. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
United States
Donnie
₹16,760
₹18,184 total
includes taxes & fees
29 Oct - 30 Oct
The Common Man Inn & Restaurant
View all properties

Top Chester Hotel Reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Spacious suite. Good kitchen. Great scenery"
Ilya 4-night trip
Posted 9 hours ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"The setting is beautiful at the base of the ski slope. Staff is very accommodating. Clean and all basic amenities were in good working order."
Alan 1-night trip
Posted 16 hours ago
Jackson Gore Village, A Vail Resorts Property
Latchis Hotel

Latchis Hotel

10/10 Excellent
"This place is a gem. I love and like the proximity to the train station, Brattleboro Food Coop, River Art School and Brattleboro Museum and Art Center, I visited twice: first with my teen son and husband, and the second by myself, and both times were great. There are signs of the passing of time in this lovely Art Deco structure, and that adds to its beauty, Super courteous staff The first time we watched a movie, so if you stay at the hotel, please treat yourself to that or some of their baskets. I missed eating at their restaurant, so I guess next time. My husband loved that there was always coffee for him, and my son loved our mini fridge and microwave. We love the history of this place and how is part of the larger arts and culture scene of Brattleboro"
Juana 2-night trip
Posted 17 hours ago
Latchis Hotel
The Jackson

The Jackson

10/10 Excellent
"Garden and grounds out back were very nice. Restaurant provided great dinner and breakfast."
Rick 2-night trip
Posted 2 days ago
The Jackson
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Our 2nd floor room with balcony was beautiful, large, clean, and with excellent amenities, also looking over the waterfront. The bed was very comfortable. We enjoyed breakfast each morning very much. Our server is friendly and helpful. We were able to get close-in parking. Desk staff were also friendly. We visited Kelleyway Gardens and spoke with Clement. She is a delightful young lady who offered good information about the area. This was our second stay and we will visit again."
Darrell 2-night trip
Posted 2 days ago
Woodstock Inn & Resort
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

8/10 Good
"What I like is the room was well stocked, very clean and the staff is very helpful. What I did not like is the parking is very inconvenient and is quite a walk which is never fun in bad weather. They need more luggage carts. It looked like they have about 5 or 6 for about a 200 room hotel. There was only one place on the property to get breakfast in the morning. There is a stove and refrigerator in the room. I had no idea before hand those would be available!"
Richard 2-night trip
Posted 2 days ago
Grand Summit Resort, A Vail Resorts Property
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"all was wonderful and well orchestrated"
Peter 3-night trip
Posted 2 days ago
Kimpton Taconic Hotel by IHG
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"The Dalmatian behind the front desk"
April 2-night trip
Posted 2 days ago
Pointe at Castle Hill Resort
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

8/10 Good
"Lovely setting and cozy atmosphere. No coffee maker or mini fridge in room due to electrical system. Pool, hot tub, steam room and sauna were good. Needs to be managed a little better."
Nancy 3-night trip
Posted 6 days ago
The Equinox Golf Resort And Spa

Frequently asked questions

Searching for hotels with bars in Chester?
Chester features 67 hotels and other accommodation options to choose from, and likely many will have a bar where you can enjoy drink after exploring the city. While you're here, you can check out DaVallia Art & Accents and Bonnie's Bundles Dolls.
What are the best hotels with bars in Chester?
Here are some favourite hotels with bars in and around Chester: Fullerton Inn: Inn with restaurant. Enjoy the bar, free breakfast and free WiFi. Stone Hearth Inn and Eatery: Resort with 4 restaurants. Enjoy the 2 bars, free WiFi and free valet parking. Woodstock Inn & Resort: B&B with restaurant. Enjoy the bar, free WiFi and free parking. The Jackson: Resort with restaurant. Enjoy the bar, free WiFi and full-service spa. Grand Summit Resort, A Vail Resorts Property: Hotel with restaurant. Enjoy the bar, free WiFi and free parking.
What is there to do in Chester?
To experience the area's highlights, consider visiting Vermont Country Store, Lowell Lake State Park and Connecticut River State Park, and then find a cosy spot for a nightcap. Other places to see include DaVallia Art & Accents and Bonnie's Bundles Dolls. Chester is known for its coffee shops, ski slopes and shops.
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 temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.
How can I get to Chester and around the area?
Here are some of your transportation options in and around Chester: Fly into Springfield, VT (VSF-Hartness State), which is located 6.6 mi (10.7 km) away. Otherwise, look for flights into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.4 mi (40.8 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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