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

Chester Bar Hotel

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Check availability on Chester Bar Hotel

Tonight
15 Aug - 16 Aug
Tomorrow
16 Aug - 17 Aug
Next weekend
21 Aug - 23 Aug
In two weeks
28 Aug - 30 Aug

Our top choices for Chester hotels with a bar

1. Fullerton Inn

Fullerton Inn
Chester Depot
United States
Kirsty
HK$1,091
HK$1,189 total
includes taxes & fees
31 Aug - 1 Sept
Fullerton Inn

2. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Bradley
HK$718
HK$797 total
includes taxes & fees
1 Sept - 2 Sept
The Upper Pass Lodge at Magic Mountain

3. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
Stephen
HK$1,248
HK$1,422 total
includes taxes & fees
16 Aug - 17 Aug
Pointe at Castle Hill Resort

4. Bromley View Inn

Bromley View Inn
Bondville
United States
Josh
HK$600
HK$660 total
includes taxes & fees
20 Aug - 21 Aug
Bromley View Inn

5. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Rula
HK$1,546
HK$1,974 total
includes taxes & fees
16 Aug - 17 Aug
The Inn at Weathersfield

6. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
United States
Denis
HK$1,052
HK$1,142 total
includes taxes & fees
7 Sept - 8 Sept
The Common Man Inn & Restaurant

7. Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
Ludlow
United States
Kristina
HK$1,145
HK$1,260 total
includes taxes & fees
24 Aug - 25 Aug
Main and Mountain Bar & Motel

8. The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
Stratton
United States
Luis
HK$1,024
HK$1,239 total
includes taxes & fees
1 Sept - 2 Sept
The Black Bear Lodge at Stratton Mountain Resort

9. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
United States
Russell
HK$1,091
HK$1,318 total
includes taxes & fees
17 Aug - 18 Aug
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
United States
Cynthia
HK$915
HK$1,112 total
includes taxes & fees
7 Sept - 8 Sept
Jackson Gore Village, A Vail Resorts Property
View all properties

Top Chester Hotel Reviews

Latchis Hotel

Latchis Hotel

10/10 Excellent
"Very comfy bed, lovely staff. Right in the center of Brattleboro!"
Justine 1-night trip
Posted 19 hours ago
Latchis Hotel
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"The room was clean and quiet and the air conditioning worked well. There is a full breakfast and a nice work out room. This is the second time I have stayed at this Best Western, and I will stay there again the next time I am in Keane NH."
Daniel 1-night trip
Posted 3 days ago
Best Western Plus Keene Hotel
On The River Inn

On The River Inn

10/10 Excellent
"Everything was good I cannot complain"
Graziella 1-night trip
Posted 4 days ago
On The River Inn
The Jackson

The Jackson

10/10 Excellent
"Wonderful place to rest and enjoy the beautiful town and scenery"
Geneva 1-night trip
Posted 6 days ago
The Jackson
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Perfect"
zhuang 4-night trip
Posted 8 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Amazing! Will visit again."
Leah 4-night trip
Posted 8 days ago
Woodstock Inn & Resort
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

8/10 Good
"Good place to stay, but not great."
Sean 2-night trip
Posted 11 days ago
The Equinox Golf Resort & Spa
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Excellent amenities and perfect if you're traveling with a dog to VT. Rooms are very nice albeit a bit small and very low water pressure in the shower."
Yvette 1-night trip
Posted 12 days ago
Kimpton Taconic Hotel by IHG
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

10/10 Excellent
"Very nice resort, on a beautiful landscaping"
Thomas 1-night trip
Posted 13 days ago
Grand Summit Resort, A Vail Resorts Property

Frequently asked questions

Searching for hotels with bars in Chester?
Chester features 62 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. Woodstock Inn & Resort: Resort with 4 restaurants. Enjoy the 2 bars, free WiFi and free valet parking. Keene Elm City Hotel, an Ascend Collection Hotel: Hotel with restaurant. Enjoy the bar, seasonal outdoor pool and breakfast. Kimpton Taconic Hotel by IHG: Hotel with restaurant. Enjoy the bar, free WiFi and free parking. On The River Inn: Resort with restaurant. Enjoy the bar, free WiFi and full-service spa.
What is there to do in Chester?
To experience the area's highlights, consider visiting Vermont Country Store, Lowell Lake State Park and Magic Mountain Ski Resort, 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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