aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

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Check availability on Chester Hotels with Bars

Our top choices for Chester hotels with a bar

Garden

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very Good, (436 reviews)
"Beautiful old inn Great Staff"
United States
Elizabeth A
The price is NT$4,398
NT$4,793 total
includes taxes & fees
Jun 18 - Jun 19
Fullerton Inn
Lounge

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (447 reviews)
"The staff was very friendly and helpful."
Canada
Dumitru Florin
The price is NT$2,927
NT$3,219 total
includes taxes & fees
Jun 21 - Jun 22
Bromley View Inn
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,002 reviews)
"We love staying here. It’s very clean, staff is always friendly,and the breakfast choices are great!!"
United States
Jennifer
The price is NT$3,771
NT$4,092 total
includes taxes & fees
Jun 22 - Jun 23
Best Western Plus Keene Hotel
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (40 reviews)
"The hot tub was so amazing"
United States
Mark
The price is NT$4,134
NT$4,506 total
includes taxes & fees
Jun 14 - Jun 15
Four Columns Inn
Exterior

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (895 reviews)
"Historic hotel in the heart of downtown, close to everything-- restaurants, galleries, stores, train station. Great location, wonderful staff, movie theater and pub on site!"
United States
Sharon
The price is NT$4,668
NT$5,135 total
includes taxes & fees
Jun 16 - Jun 17
Latchis Hotel
Interior entrance

The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
3.5 star property
Claremont
9.6 out of 10, Exceptional, (389 reviews)
"We have stayed at The Common Man Inn many times. It is always a treat. Right in town, very clean, restaurant is great and breakfast is perfect to start your day. The staff is very helpful and always available as well as friendly."
United States
Robert
The price is NT$4,676
NT$5,073 total
includes taxes & fees
Jun 25 - Jun 26
The Common Man Inn & Restaurant
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (284 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
The price is NT$4,989
NT$5,489 total
includes taxes & fees
Jun 18 - Jun 19
The Jackson
Sauna, aromatherapy, hot stone massages, deep-tissue massages

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
3.5 star property
Cavendish
8.8 out of 10, Excellent, (1,002 reviews)
"Great place for the family!"
United States
Stephen
The price is NT$5,354
NT$6,103 total
includes taxes & fees
Jun 25 - Jun 26
Pointe at Castle Hill Resort
Hallway

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,003 reviews)
"Great stay here "
United States
Sophia
The price is NT$7,099
NT$8,971 total
includes taxes & fees
Jun 18 - Jun 19
On The River 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, (837 reviews)
"The accommodations were clean and comfortable, the staff friendly, the on site restaurant had several delicious options, the views were amazing! "
United States
Dayna
The price is NT$4,086
NT$4,972 total
includes taxes & fees
Jun 15 - Jun 16
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
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

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"I can’t say enough about the Frontenac. The staff was sincerely friendly and went out of their way to help us with whatever we needed. We left the Fairmont Frontenac to head back to Connecticut. When we got back, my sister realized she left her Kindle in her room. We called to see if it had been found. They put us on hold got right back to us and said they had it and would send it to her address. The location is ideal. The rooms are immaculate. The people that came to our rooms for the turndown service. We’re very sweet with big smiles on their face as they brought us freshwater/free every evening. This is the third time I’ve been to the Frantenac. I’m sure it won’t be our last."
Richard 1-night trip
Posted 5 hours ago
Kimpton Taconic Hotel by IHG

Frequently asked questions

Searching for hotels with bars in Chester?
Chester features 60 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. Woodstock Inn & Resort: Resort with 4 restaurants. Enjoy the 2 bars, free WiFi, and free valet parking. Kimpton Taconic Hotel by IHG: Hotel with restaurant. Enjoy the bar, seasonal outdoor pool, and breakfast. Latchis Hotel: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Hampton Inn Brattleboro: 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 Saxtons River Recreation Area, 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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