Search Hotels with a Bar in Chester

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Check availability on Chester Hotels with a Bar

Our top choices for Chester hotels with a bar

Garden
Fullerton Inn

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very good, (402)
"Lovely stay"
United States
Christine
The price is ₹11,595
₹12,639 total
includes taxes & fees
14 Dec - 15 Dec
Fullerton Inn
Lounge
Bromley View Inn

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (403)
"Clean and great location with fun lounge area."
United States
Marshall
Bromley View Inn
Land view from property
Four Columns Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (14)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn
Free WiFi, bed sheets
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
Stratton
7.6 out of 10, Good, (940)
"We like that getting to Stratton Mountain and the downtown area was very walkable or easy to get there by regularly running shuttle buses."
United States
Mark
The price is ₹16,477
₹19,938 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Black Bear Lodge at Stratton Mountain Resort
Hallway
On The River Inn

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1001)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is ₹17,363
₹22,398 total
includes taxes & fees
22 Dec - 23 Dec
On The River Inn
Interior
The Inn at Weathersfield

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (70)
"The location of the Inn was in an area that was just wonderful. Staff was very friendly and the menu options were very tasty. Room was clean and well maintained. "
United States
Joshua
The Inn at Weathersfield
Restaurant
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1001)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is ₹12,494
₹13,556 total
includes taxes & fees
14 Dec - 15 Dec
Best Western Plus Keene Hotel
Front of property
COHO Inn & Motor Lodge

COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
2.0 star property
Weston
9.2 out of 10, Wonderful, (44)
"The owner was delightful and very accommodating. "
United States
Karen
The price is ₹11,961
₹13,037 total
includes taxes & fees
16 Dec - 17 Dec
COHO Inn & Motor Lodge
Sauna, aromatherapy, hot stone massages, deep-tissue massages
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
3.5 star property
Cavendish
8.8 out of 10, Excellent, (924)
"Great place to stay while skiing at okemo"
United States
Ken
The price is ₹14,280
₹16,279 total
includes taxes & fees
14 Dec - 15 Dec
Pointe at Castle Hill Resort
Interior entrance
The Common Man Inn & Restaurant

The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
3.5 star property
Claremont
9.6 out of 10, Exceptional, (370)
"Great place to stay! "
United States
Candace M
The price is ₹11,244
₹12,200 total
includes taxes & fees
21 Dec - 22 Dec
The Common Man Inn & Restaurant
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Great place to stay while skiing at okemo"
Ken 1-night trip
Posted 5 days ago
Pointe at Castle Hill Resort

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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 in the area, you can check out Stratton Mountain Resort.
What are the best hotels with bars in Chester?
Here are some favourite hotels with bars in and around Chester: Woodstock Inn & Resort: Resort with 4 restaurants. Enjoy the 2 bars, free WiFi and free valet parking. The Shire Woodstock: Hotel with restaurant. Enjoy the bar, seasonal outdoor pool and breakfast. Kimpton Taconic Hotel by IHG: Hotel with 4 restaurants. Enjoy the 2 bars, free parking and seasonal outdoor pool. The Equinox Golf Resort & Spa: B&B with restaurant. Enjoy the bar, free WiFi and free parking. Hampton Inn and Suites Manchester: 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 Stratton Mountain Resort, Grafton Historical Society and Vermont Country Store, 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.