Find Hotels with Bars in Chester, VT

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Top Chester Hotels with Bars

Garden
Fullerton Inn

Fullerton Inn

2.5 star property
Chester Depot
8.2 out of 10, Very Good, (402)
"Lovely stay"
United States
Christine
$129 nightly
The price is $141
Dec 7 - Dec 8
Total with taxes and fees
Fullerton Inn
Lounge
Bromley View Inn

Bromley View Inn

3.5 star property
Bondville
9.0 out of 10, Wonderful, (401)
"Overall a decent stay."
United States
Libin
$92 nightly
The price is $101
Dec 7 - Dec 8
Total with taxes and fees
Bromley View Inn
Garden
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (13)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
$125 nightly
The price is $137
Dec 16 - Dec 17
Total with taxes and fees
Four Columns Inn
Exterior
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3.0 star property
Brownsville
9.0 out of 10, Wonderful, (777)
"Very welcoming, spacious, clean. Perfect for a family of 4. "
United States
Kathleen
$134 nightly
The price is $146
Dec 8 - Dec 9
Total with taxes and fees
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Premium bedding, individually decorated, individually furnished, desk
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3.0 star property
Keene
8.4 out of 10, Very Good, (1000)
"Great staff, clean room, nice breakfast"
United States
DORTHY
$139 nightly
The price is $151
Dec 7 - Dec 8
Total with taxes and fees
Best Western Plus Keene Hotel
Interior
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
$286 nightly
The price is $311
Dec 14 - Dec 15
Total with taxes and fees
The Inn at Weathersfield
Premium bedding, desk, blackout drapes, iron/ironing board
The Common Man Inn & Restaurant

The Common Man Inn & Restaurant

3.5 star property
Claremont
9.6 out of 10, Exceptional, (369)
"Great place to stay! "
United States
Candace M
$139 nightly
The price is $151
Dec 14 - Dec 15
Total with taxes and fees
The Common Man Inn & Restaurant
Exclusive Suite, 3 Bedrooms, Kitchenette, Mountain View - Pet Friendly | 1 bedroom, desk, iron/ironing board, free WiFi
The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain

2.5 star property
Londonderry
8.2 out of 10, Very Good, (686)
"Wery good diner"
United States
Yelena
$107 nightly
The price is $118
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Upper Pass Lodge at Magic Mountain
Terrace/patio
On The River Inn

On The River Inn

4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1000)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
$151 nightly
The price is $166
Dec 8 - Dec 9
Total with taxes and fees
On The River Inn
Restaurant
COHO Inn & Motor Lodge

COHO Inn & Motor Lodge

2.0 star property
Weston
9.2 out of 10, Wonderful, (43)
"The owner was delightful and very accommodating. "
United States
Karen
$134 nightly
The price is $147
Dec 15 - Dec 16
Total with taxes and fees
COHO Inn & Motor Lodge
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

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"The staff are amazing! So friendly and welcoming. The lodge is so cute! The rooms were spotless and the hottub sparkling clean. The shuttle service until 10 pm was fantastic and the shuttle driver was very nice. We can't wait to visit again! "
Barbara 1-night trip
Posted 12 hours ago
The Black Bear Lodge at Stratton Mountain Resort

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 in the area, you can check out Stratton Mountain Resort.
What are the best hotels with bars in Chester?
Here are a few of the top 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 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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