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

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Check availability on Chester Hotels with Bars

Tonight
Oct 24 - Oct 25
Tomorrow
Oct 25 - Oct 26
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

Our top choices for Chester hotels with a bar

A cozy living room with a stone fireplace, a leather sofa set, a wooden coffee table, and a patterned rug.
A two-story building with a central entrance, a balcony with railings, and a sign indicating it is a lodging and fine dining establishment.
A bedroom with a bed, a bedside table, a lamp, a mirror, a dresser, a window, and a ceiling fan.
A well-maintained garden with a variety of plants and flowers, a wooden pergola, and a gravel path.

1. Fullerton Inn

Fullerton Inn
Chester Depot
United States
Tim
NT$4,206
NT$4,584 total
includes taxes & fees
Nov 10 - Nov 11
Fullerton Inn
A two-story building with a red facade, a balcony on the second floor, and a parking lot in front.
A living room with a fireplace, a sofa, a coffee table, and a dining area with chairs and a table.
A Christmas tree decorated with lights, ornaments, and a bow.
A bar area with a sign reading "MAGIC" and "featured Vermont beers".

2. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Lynne
NT$3,012
NT$3,449 total
includes taxes & fees
Oct 26 - Oct 27
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.
A spacious lobby with a fireplace, leather seating, and a chandelier.
An indoor swimming pool with four chairs and a hot tub.
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
NT$5,247
NT$5,982 total
includes taxes & fees
Oct 26 - Oct 27
Pointe at Castle Hill Resort
A large, multi-story building with a symmetrical facade, multiple chimneys, and a well-maintained garden with evergreen trees.
A rustic dining area with wooden beams, tables, chairs, and a fireplace.
A bedroom with a large bed, a bedside table, a lamp, and a view of the outdoors through a sliding door.
An outdoor event space with tables set for dining, surrounded by a covered area with a transparent roof.

4. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Dorrie
NT$7,391
NT$9,256 total
includes taxes & fees
Nov 5 - Nov 6
The Inn at Weathersfield
A cozy room with a fireplace, green sofas, a pool table, and a lamp.
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 hotel hallway with wooden walls, a reception desk, and a sign indicating 'Employees Only'.
A deck with white railings overlooking a forested area and a mountain in the distance.

5. Bromley View Inn

Bromley View Inn
Bondville
United States
BARBARA
NT$2,804
NT$3,085 total
includes taxes & fees
Nov 22 - Nov 23
Bromley View Inn
A large two-story house with a front porch and a well-maintained lawn.
A cozy interior with a bar area, wooden furniture, and a Christmas tree.
An aerial view of a residential area with houses, a tennis court, and a swimming pool.
A spacious room with high ceilings, wooden beams, large windows, and tables and chairs arranged for dining.

6. The Landgrove

The Landgrove
Londonderry
United States
Alan
NT$6,207
NT$6,766 total
includes taxes & fees
Oct 26 - Oct 27
The Landgrove
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, red sofas, a wooden coffee table, and a television.
A hotel room with a bed, a nightstand, a lamp, a door, and a view into another room with a couch and a window.

7. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Brandon
NT$8,773
NT$9,562 total
includes taxes & fees
Oct 26 - Oct 27
Castle Hill Resort And Spa
A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.
A balcony with a stone wall and wooden railing overlooking a grassy area with a building in the background.
A golf course with rolling hills, trees, and a distant mountain range.
A hotel with a swimming pool area, including two hot tubs and lounge chairs.

8. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
United States
Adriana
NT$6,021
NT$7,315 total
includes taxes & fees
Nov 18 - Nov 19
Jackson Gore Village, A Vail Resorts Property
A multi-story hotel with a central courtyard and a reflective water feature.
A group of people gathered around a fire pit in a snowy outdoor setting with a large building in the background.
A spacious living area with a staircase, patterned sofas, a coffee table, and a decorative wall piece.
A living room with a fireplace, a sofa, a coffee table, and a television.

9. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
United States
Sara
NT$4,527
NT$5,473 total
includes taxes & fees
Oct 27 - Oct 28
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
A cozy living room with a fireplace, leather furniture, and a coffee table with a puzzle.
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.
A wooden interior with a pool, benches, and a clock.

10. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
United States
Anna
NT$4,225
NT$4,584 total
includes taxes & fees
Nov 1 - Nov 2
The Common Man Inn & Restaurant
View all properties

Top Chester Hotel Reviews

Latchis Hotel

Latchis Hotel

8/10 Good
"It’s located with restaurants within walking distance. It is well maintained for a historic hotel with probably about 15 steps in the lobby before you get to the elevator. It was noisy some nights due to being in the city and having residents living life. Staff was wonderful. Again location was great to see Buffalo—Niagara is 20 min away, Botanic Garden and Eternal Flame about the same. We enjoyed our stay."
Matthew 1-night trip
Posted 3 days ago
Latchis Hotel
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

8/10 Good
"The property is a beautiful old hotel, but you can tell they are having a hard time keeping it up. The rooms are big and cozy at the same time, the beds comfortable but the bathroom had some ventilation issues and therefore was a little moldy. While the pool was great, it was a shame the sauna was not working. All in all a nice stay though."
Sylvie 3-night trip
Posted 3 days ago
The Equinox Golf Resort And Spa
Colonial Motel

Colonial Motel

8/10 Good
"The rooms are quite large. There were a lot of unfinished projects going on, so the property was messy and slightly unkempt. The breakfast was terrible. Trash bags were left out attracting skunks. Price made it a 4 star."
Andrea 3-night trip
Posted 5 days ago
Colonial Motel
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Beautiful resort with amazing beds! Very comfortable."
Sara 4-night trip
Posted 6 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Fullerton Inn

Fullerton Inn

10/10 Excellent
"Stayed there 7yrs.ago and had another great experience this time, Cloe our waitress was excellent and made our dining alot of fun."
Tim 1-night trip
Posted 11 days ago
Fullerton Inn

Frequently asked questions

Searching for hotels with bars in Chester?
Chester features 67 properties to choose from, and likely many will have a bar where you can enjoy an evening cocktail after a day out exploring. 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 a few of the top 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 cozy spot for a nightcap. Other places to see include DaVallia Art & Accents and Bonnie's Bundles Dolls. Chester is known for its coffeehouses, 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 temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches 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 from the city center. 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, consider renting a car to take in more sights.

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