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

Tonight
Sep 9 - Sep 10
Tomorrow
Sep 10 - Sep 11
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Chester hotels with a bar

1. Fullerton Inn

Fullerton Inn
Chester Depot
United States
Kirsty
NT$4,696
NT$5,119 total
includes taxes & fees
Sep 10 - Sep 11
Fullerton Inn

2. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Terry
NT$2,886
NT$3,304 total
includes taxes & fees
Sep 10 - Sep 11
The Upper Pass Lodge at Magic Mountain

3. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
David
NT$4,527
NT$5,161 total
includes taxes & fees
Sep 10 - Sep 11
Pointe at Castle Hill Resort

4. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Rula
NT$5,585
NT$7,247 total
includes taxes & fees
Sep 12 - Sep 13
The Inn at Weathersfield

5. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
United States
Zulma
NT$5,208
NT$6,327 total
includes taxes & fees
Sep 30 - Oct 1
Jackson Gore Village, A Vail Resorts Property

6. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
United States
Victoria
NT$4,368
NT$4,739 total
includes taxes & fees
Sep 13 - Sep 14
The Common Man Inn & Restaurant

7. COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
Weston
United States
Raedene
NT$5,616
NT$6,122 total
includes taxes & fees
Sep 10 - Sep 11
COHO Inn & Motor Lodge

8. Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
Ludlow
United States
Paull
NT$5,063
NT$5,570 total
includes taxes & fees
Sep 15 - Sep 16
Main and Mountain Bar & Motel

9. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
United States
Russell
NT$3,992
NT$4,871 total
includes taxes & fees
Sep 10 - Sep 11
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Mirco
NT$7,209
NT$7,858 total
includes taxes & fees
Sep 14 - Sep 15
Castle Hill Resort And Spa
View all properties

Top Chester Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Wonderful experience. Beautiful, clean room and friendly/helpful front desk"
Darlene 1-night trip
Posted 4 hours ago
Pointe at Castle Hill Resort
Latchis Hotel

Latchis Hotel

8/10 Good
"Clean outer windows. Fix leaky faucet in bathroom. Otherwise good"
delphine 1-night trip
Posted 10 hours ago
Latchis Hotel
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Beautiful property, really special! Easy walk to shops."
crystal 1-night trip
Posted 2 days ago
Woodstock Inn & Resort
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Bel endroit pour passer du temps avec la famille."
Mariline 2-night trip
Posted 2 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
The Jackson

The Jackson

10/10 Excellent
"The inn and the grounds are beautifully maintained. The room was comfortable, and the restaurant on the premises was convenient but also had a great breakfast, well worth purchasing. The location was also great relative to downtown."
Vicki 1-night trip
Posted 3 days ago
The Jackson

Frequently asked questions

Searching for hotels with bars in Chester?
Chester features 63 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: Woodstock Inn & Resort: Resort with 4 restaurants. Enjoy the 2 bars, free WiFi, and free valet parking. Latchis Hotel: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Grand Summit Resort, A Vail Resorts Property: Resort with restaurant. Enjoy the bar, free WiFi, and full-service spa. Colonial Motel: B&B with restaurant. Enjoy the bar, free WiFi, and free parking. The Shire Woodstock: 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 Connecticut River State Park, 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.

Explore a world of travel with Expedia