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

Find Hotels with Bars in Chester, VT

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester Hotels with Bars

Next weekend
Jul 31 - Aug 2
In two weeks
Aug 7 - Aug 9

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, (443 reviews)
"The building was very quaint and had a historical vibe."
United States
Rick
The price is NT$5,148
NT$5,611 total
includes taxes & fees
Jul 29 - Jul 30
Fullerton Inn
Interior entrance

The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
3.5 star property
Claremont
9.6 out of 10, Exceptional, (406 reviews)
"Beautifully decorated old mill right on the river with great restaurant"
United States
Denis
The price is NT$4,779
NT$5,185 total
includes taxes & fees
Aug 16 - Aug 17
The Common Man Inn & Restaurant
Interior

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (80 reviews)
"Great location, service and restaurant "
United States
LUDJANE
The price is NT$6,058
NT$7,795 total
includes taxes & fees
Jul 27 - Jul 28
The Inn at Weathersfield
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, (1,003 reviews)
"Great place for the family!"
United States
Stephen
The price is NT$5,472
NT$6,238 total
includes taxes & fees
Aug 9 - Aug 10
Pointe at Castle Hill Resort
Lounge

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (453 reviews)
"staff actually treated you like family and not another customer & Clean room & relaxing backyard to watch the sunset & great breakfast"
United States
Josh
The price is NT$2,475
NT$2,723 total
includes taxes & fees
Aug 2 - Aug 3
Bromley View Inn
Front of property

Castle Hill Resort And Spa

Castle Hill Resort And Spa
3.5 star property
Cavendish
9.0 out of 10, Wonderful, (120 reviews)
"This was our second time staying here and it never disappoints! I booked this trip during our kids' spring break for a quick getaway and to use the amazing heated outdoor pool. It's a great location convenient to all the amazing sites Vermont has to offer. Would love to go back again in the fall!"
United States
Jennifer
The price is NT$8,712
NT$9,497 total
includes taxes & fees
Aug 6 - Aug 7
Castle Hill Resort And Spa
Property entrance

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
3.0 star property
Jackson Gore Base Area
8.6 out of 10, Excellent, (874 reviews)
"Great family friendly location!"
United States
Cynthia
The price is NT$5,979
NT$7,264 total
includes taxes & fees
Aug 25 - Aug 26
Jackson Gore Village, A Vail Resorts Property
WiFi (free), bed sheets

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, (1,003 reviews)
"The beds were very squeaky. Pillows too big"
United States
Patti
The price is NT$4,342
NT$5,253 total
includes taxes & fees
Jul 28 - Jul 29
The Black Bear Lodge at Stratton Mountain Resort
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,000 reviews)
"Staff was very friendly, accommodating, and attentive to our needs. Room was clean and comfortable!"
United States
Helen
The price is NT$4,500
NT$4,883 total
includes taxes & fees
Jul 27 - Jul 28
Best Western Plus Keene Hotel
Restaurant

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, (702 reviews)
"Charming rustic inn. Staff were delightful and food was great. "
United States
Bradley
The price is NT$3,913
NT$4,344 total
includes taxes & fees
Aug 24 - Aug 25
The Upper Pass Lodge at Magic Mountain
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.
View all properties

Top Chester Hotel Reviews

Fullerton Inn

Fullerton Inn

10/10 Excellent
"This may be the first review I’ve ever actually done. I was pleasantly surprised with our stay at the Fullerton Inn. I brought my granddaughter for a night away and I loved how open, large and clean, yet so cozy, it felt when walking in the door. Having the restaurant there was so convenient and there were so many places within steps to see and shop. It turned out to be just what I needed. The rooms were clean and spacious enough."
Nancy 1-night trip
Posted 14 hours ago
Fullerton Inn

Frequently asked questions

Searching for hotels with bars in Chester?
Chester features 64 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. 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 breakfast, and free WiFi. Best Western Plus Keene Hotel: 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 DaVallia Art & Accents, Vermont Country Store, and Lowell Lake State Park, and then find a cozy spot for a nightcap. Other places to see include 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.

Explore a world of travel with Expedia