The Best Hotels with Bars in Chester, VT from NT$3,299 in 2026

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

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Our top choices for Chester hotels with a bar

Iron/ironing board (on request), WiFi (free), bed sheets

1. Fullerton Inn

Chester Depot

Kirsty

NT$4,688

NT$5,110 total

includes taxes & fees

Sep 15 - Sep 16

Romantic Room, 1 Bedroom, Jetted Tub - Non-Pet Friendly | 1 bedroom, desk, iron/ironing board (on request), WiFi (free)

2. The Upper Pass Lodge at Magic Mountain

Londonderry

Terry

NT$2,881

NT$3,299 total

includes taxes & fees

Sep 13 - Sep 14

Sauna, aromatherapy, hot stone massages, deep-tissue massages

Suite, 1 King Bed, Sofa Bed & Full Kitchen | Private kitchen | Coffee/tea maker

3. Pointe at Castle Hill Resort

Cavendish

David

NT$5,055

NT$5,763 total

includes taxes & fees

Sep 16 - Sep 17

King Room with Garden View | Egyptian cotton sheets, premium bedding, memory foam beds, WiFi (free)

King Room with Spa Bath | Egyptian cotton sheets, premium bedding, memory foam beds, WiFi (free)

4. The Inn at Weathersfield

Perkinsville

Rula

NT$5,576

NT$7,236 total

includes taxes & fees

Sep 12 - Sep 13

5. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

Zulma

NT$5,200

NT$6,317 total

includes taxes & fees

Sep 30 - Oct 1

6. The Common Man Inn & Restaurant

Claremont

Victoria

NT$4,361

NT$4,732 total

includes taxes & fees

Sep 13 - Sep 14

30-inch flat-screen TV with digital channels, Netflix, Hulu

7. COHO Inn & Motor Lodge

Weston

Raedene

NT$5,616

NT$6,122 total

includes taxes & fees

Sep 13 - Sep 14

8. Main and Mountain Bar & Motel

Ludlow

Paull

NT$5,055

NT$5,561 total

includes taxes & fees

Sep 16 - Sep 17

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Top Chester Hotel Reviews

Pointe at Castle Hill Resort

10/10 Excellent

"Wonderful experience. Beautiful, clean room and friendly/helpful front desk"

Woodstock Inn & Resort

10/10 Excellent

"Beautiful property, really special! Easy walk to shops."

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."

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.

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Treat yourself

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Check availability on Chester Hotels with Bars

Our top choices for Chester hotels with a bar

1. Fullerton Inn

2. The Upper Pass Lodge at Magic Mountain

3. Pointe at Castle Hill Resort

4. The Inn at Weathersfield

5. Jackson Gore Village, A Vail Resorts Property

6. The Common Man Inn & Restaurant

7. COHO Inn & Motor Lodge

8. Main and Mountain Bar & Motel

9. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10. Castle Hill Resort And Spa

Top Chester Hotel Reviews

Pointe at Castle Hill Resort

Woodstock Inn & Resort

The Jackson

Frequently asked questions

Explore a world of travel with Expedia

Find Hotels with Bars in Chester, VT

Change your mind

Treat yourself

Be picky

Check availability on Chester Hotels with Bars

Our top choices for Chester hotels with a bar

1. Fullerton Inn

2. The Upper Pass Lodge at Magic Mountain

3. Pointe at Castle Hill Resort

4. The Inn at Weathersfield

5. Jackson Gore Village, A Vail Resorts Property

6. The Common Man Inn & Restaurant

7. COHO Inn & Motor Lodge

8. Main and Mountain Bar & Motel

9. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10. Castle Hill Resort And Spa

Top Chester Hotel Reviews

Pointe at Castle Hill Resort

Woodstock Inn & Resort

The Jackson

Frequently asked questions

Explore a world of travel with Expedia