TOP Hotels with a Bar in Chester, VT for 2026

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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.

1. Fullerton Inn

Chester Depot

Tim

₹13,223 total

includes taxes & fees

24 Nov - 25 Nov

A pug sitting on a leather chair with a mug labeled "Magic Mt." in a warmly lit indoor setting.

2. The Upper Pass Lodge at Magic Mountain

Londonderry

Silvia

₹9,065 total

includes taxes & fees

16 Nov - 17 Nov

A formal dining room with ornate wood paneling, multiple tables set for dining, and a mirror reflecting the room's decor.

3. Pointe at Castle Hill Resort

Cavendish

Cristian

₹17,261 total

includes taxes & fees

15 Dec - 16 Dec

A deck with white railings overlooking a forested area and a mountain in the distance.

4. Bromley View Inn

Bondville

BARBARA

₹7,581 total

includes taxes & fees

22 Nov - 23 Nov

A large, multi-story building with a symmetrical facade, multiple chimneys, and a well-maintained garden with evergreen trees.

5. The Inn at Weathersfield

Perkinsville

Rula

₹24,034 total

includes taxes & fees

3 Dec - 4 Dec

A modern two-story building with a red roof, surrounded by a well-maintained garden with various plants and a stone pathway.

6. The Landgrove

Londonderry

Alan

₹18,530 total

includes taxes & fees

16 Nov - 17 Nov

A large stone building with a steep roof, surrounded by dense forest and hills.

7. Castle Hill Resort And Spa

Cavendish

Brandon

₹16,890 total

includes taxes & fees

15 Nov - 16 Nov

A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.

8. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

Adriana

₹21,752 total

includes taxes & fees

19 Nov - 20 Nov

A cozy room with a wooden staircase, a fireplace, a sofa, and a patterned rug.

9. The Common Man Inn & Restaurant

Claremont

Anna

₹13,224 total

includes taxes & fees

15 Nov - 16 Nov

A stone fire pit with chairs around it, set in a grassy area with trees and a large building in the background.

10. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

Richard

₹14,762 total

includes taxes & fees

17 Nov - 18 Nov

View all properties

Top Chester Hotel Reviews

The Inn at Weathersfield

Perkinsville

8/10 Good

Anonymous traveller

A two-story building with a bar and restaurant on the ground floor, a vintage car parked in front, and a sign indicating "Main Mountain".

Main and Mountain Bar & Motel

Ludlow

10/10 Excellent

Justin

A two-story building with a porch, American flag, and two white rocking chairs.

The Reluctant Panther Inn and Restaurant

Manchester Village Historic District

10/10 Excellent

Peter

A swimming pool with lounge chairs and umbrellas, surrounded by trees and a building.

Kimpton Taconic Hotel by IHG

Manchester Village Historic District

10/10 Excellent

What a wonderful hotel, of our trip to New England, this was probably our biggest (wonderful) surprise. It's just a joyous place. The room was wonderful, the staff in the bar and restaurant were amazing and the location is just truly wonderful. The reception staff when we checked on, were professional, but very disimterested and were more interested in themselves and their chat, but, it was a minor irritation in a wonderful stay. The restaurant serves great food and wine too, was busy, book...

Anonymous traveller

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

Four Columns Inn

Newfane

8/10 Good

We only had an opportunity to stay one night stay but overall had a very pleasant experience. The room was really nice apart from the wierd location of the television . The bar was "like a real bar " and the lady serving was great ( as was the live entertainment ). Our dining experience has room for improvement although the staff were really nice . Breakfast was "OK" . Good coffee . The owner was extremely friendly and the location and grounds are beautiful . Check in was a little fluffy - I...

Philip

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

10/10 Excellent

We were there at the end of May. We particularly liked the view of the mountain from our window. The hotel is split over several attractive buildings, all sited on what used to be a ski resort. We were told that it was a "time share" which means that there is no daily maid service, which made no difference to us at all. The accommodation was excellent, so much so that we extended our stay. The staff were very welcoming. The large indoor pool was also very impressive. There is also an outdoor...

Anonymous traveller

The Upper Pass Lodge at Magic Mountain

Londonderry

10/10 Excellent

Timothy

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

10/10 Excellent

Amol

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.

Search Hotels with a Bar in Chester

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester hotels with a bar

1. Fullerton Inn

2. The Upper Pass Lodge at Magic Mountain

3. Pointe at Castle Hill Resort

4. Bromley View Inn

5. The Inn at Weathersfield

6. The Landgrove

7. Castle Hill Resort And Spa

8. Jackson Gore Village, A Vail Resorts Property

9. The Common Man Inn & Restaurant

10. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Top Chester Hotel Reviews

The Inn at Weathersfield

8/10 Good

Frequently Asked Questions

Searching for hotels with bars in Chester?

What are the best hotels with bars in Chester?

What is there to do in Chester?

When is the best time to visit Chester?

How can I get to Chester and around the area?

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