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Our top choices for Chester hotels with a bar
1. Fullerton Inn
Fullerton Inn2.5 star property
Chester Depot
8.2 out of 10, Very good, (466 reviews)
8.2/10
Very good
(466 reviews)
"Stayed there 7yrs.ago and had another great experience this time,
Cloe our waitress was excellent and made our dining alot of fun."
"Stayed there 7yrs.ago and had another great experience this time,
Cloe our waitress was excellent and made our dining alot of fun."
Tim
$129 nightly
The price is $141
$141 total
Nov 24 - Nov 25
Total with taxes and fees
2. The Upper Pass Lodge at Magic Mountain
The Upper Pass Lodge at Magic Mountain2.5 star property
Londonderry
8.2 out of 10, Very good, (715 reviews)
8.2/10
Very good
(715 reviews)
"Loretta was so helpful and friendly."
"Loretta was so helpful and friendly."Silvia
$88 nightly
The price is $96
$96 total
Nov 16 - Nov 17
Total with taxes and fees
3. Pointe at Castle Hill Resort
Pointe at Castle Hill Resort3.5 star property
Cavendish
8.8 out of 10, Excellent, (1,001 reviews)
8.8/10
Excellent
(1,001 reviews)
"Amazing rooms, sweet staff, great amenities - gorgeous location!"
"Amazing rooms, sweet staff, great amenities - gorgeous location!"Cristian
$177 nightly
The price is $193
$193 total
Nov 15 - Nov 16
Total with taxes and fees
4. Bromley View Inn
Bromley View Inn3.5 star property
Bondville
9.0 out of 10, Wonderful, (504 reviews)
9.0/10
Wonderful
(504 reviews)
"Great amenities, fantastic views, very clean, excellent breakfast!"
"Great amenities, fantastic views, very clean, excellent breakfast!"BARBARA
$81 nightly
The price is $90
$90 total
Nov 22 - Nov 23
Total with taxes and fees
5. The Inn at Weathersfield
The Inn at Weathersfield4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (83 reviews)
9.8/10
Exceptional
(83 reviews)
"Breakfast was very good.
Had dinner at the restaurant & it was excellent"
"Breakfast was very good.
Had dinner at the restaurant & it was excellent"Rula
$236 nightly
The price is $257
$257 total
Dec 3 - Dec 4
Total with taxes and fees
6. The Landgrove
The Landgrove3.5 star property
Londonderry
9.4 out of 10, Exceptional, (15 reviews)
9.4/10
Exceptional
(15 reviews)
"Had a great stay, room was set up with a very comfortable Home feel, not a sterile Hotel."
"Had a great stay, room was set up with a very comfortable Home feel, not a sterile Hotel."Alan
$166 nightly
The price is $181
$181 total
Nov 18 - Nov 19
Total with taxes and fees
7. Castle Hill Resort And Spa
Castle Hill Resort And Spa3.5 star property
Cavendish
9.0 out of 10, Wonderful, (127 reviews)
9.0/10
Wonderful
(127 reviews)
"I promise, especially if you’re staying in the condo buildings you will love it"
"I promise, especially if you’re staying in the condo buildings you will love it"Brandon
$167 nightly
The price is $182
$182 total
Nov 15 - Nov 16
Total with taxes and fees
8. Jackson Gore Village, A Vail Resorts Property
Jackson Gore Village, A Vail Resorts Property3.0 star property
Jackson Gore Base Area
8.6 out of 10, Excellent, (973 reviews)
8.6/10
Excellent
(973 reviews)
"Excellent place to stay!! The breakfas it good, bed comfortables and the view is nice."
"Excellent place to stay!! The breakfas it good, bed comfortables and the view is nice."Adriana
$210 nightly
The price is $231
$231 total
Nov 19 - Nov 20
Total with taxes and fees
9. The Common Man Inn & Restaurant
The Common Man Inn & Restaurant3.5 star property
Claremont
9.6 out of 10, Exceptional, (450 reviews)
9.6/10
Exceptional
(450 reviews)
"We enjoyed our stay here."
"We enjoyed our stay here."Anna
$144 nightly
The price is $156
$156 total
Nov 15 - Nov 16
Total with taxes and fees
10. Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Holiday Inn Club Vacations Mount Ascutney Resort by IHG3.0 star property
Brownsville
9.0 out of 10, Wonderful, (900 reviews)
9.0/10
Wonderful
(900 reviews)
"Great staff and very good food at the resturant. Will come back in the future!"
"Great staff and very good food at the resturant. Will come back in the future!"Richard
$144 nightly
The price is $157
$157 total
Nov 17 - Nov 18
Total with taxes and fees
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.
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.
Top Chester Hotel Reviews
The Inn at Weathersfield
The Inn at WeathersfieldPerkinsville
10/10 Excellent
Great Inn.
Great Inn.
Robert
Fullerton Inn
Fullerton InnChester Depot
10/10 Excellent
Loved the place, it’s old so full of charm and perhaps not so easy, stairs, rumpled flooring but I like such places. Had dinner which was very good, has a nice little pub as well. Everyone I encountered was pleasant.
Loved the place, it’s old so full of charm and perhaps not so easy, stairs, rumpled flooring but I like such places. Had dinner which was very good, has a nice little pub as well. Everyone I encountered was pleasant.
Catherine
The Common Man Inn & Restaurant
The Common Man Inn & RestaurantClaremont
10/10 Excellent
I had a very comfortable stay. No complaints.
Many great cable TV channels, refrigerator, microwave, coffee maker, My room had a river view (pictured).
I had a very comfortable stay. No complaints.
Many great cable TV channels, refrigerator, microwave, coffee maker, My room had a river view (pictured).
Robert
Pointe at Castle Hill Resort
Pointe at Castle Hill ResortCavendish
10/10 Excellent
This is the second time we've stayed in a Suite room. King sized bed in the BR; kitchen with full-sized appliances, LR with pull-out Queen sofa, gas fireplace, bathroom with jetted tub! Very comfortable and fully equipped. Small things were so helpful - like doormats for dirty boots, a bench for putting on boots, a closet for skis, complementary packages of New England coffee, Aveda products in the bathroom, kitchen supplies like dish soap, dishwasher detergent, sponge, towels. Then larger...
This is the second time we've stayed in a Suite room. King sized bed in the BR; kitchen with full-sized appliances, LR with pull-out Queen sofa, gas fireplace, bathroom with jetted tub! Very comfortable and fully equipped. Small things were so helpful - like doormats for dirty boots, a bench for putting on boots, a closet for skis, complementary packages of New England coffee, Aveda products in the bathroom, kitchen supplies like dish soap, dishwasher detergent, sponge, towels. Then larger...
Marion
The Inn at Manchester
The Inn at ManchesterManchester Village Historic District
10/10 Excellent
Beautifully landscaped with great location and walkable to several restaurants or easy drive. Welcoming, helpful staff and great breakfast.
Beautifully landscaped with great location and walkable to several restaurants or easy drive. Welcoming, helpful staff and great breakfast.
Mary
Main and Mountain Bar & Motel
Main and Mountain Bar & MotelLudlow
10/10 Excellent
This motel was great! You can’t beat the location for Ludlow and it made for a cozy, winter stay. Our experience at the outdoor fire pits at the bar was great and the rooms were very clean and comfortable. I would definitely go back!
This motel was great! You can’t beat the location for Ludlow and it made for a cozy, winter stay. Our experience at the outdoor fire pits at the bar was great and the rooms were very clean and comfortable. I would definitely go back!
Anonymous traveler
The Reluctant Panther Inn and Restaurant
The Reluctant Panther Inn and RestaurantManchester Village Historic District
10/10 Excellent
nice stay, friendly staff, terrific breakfast
highly recommend
nice stay, friendly staff, terrific breakfast
highly recommend
Anonymous traveler
The Landgrove
The LandgroveLondonderry
10/10 Excellent
The Inn is in a beautiful setting. The staff were very friendly and helpful. My room was spacious and a comfortable arm chair and good lamp provided a cozy place for R&R. The spacious common area & well kept grounds would be a very pleasant place to spend time with family and friends. I was advised in advance that the restaurant was not serving dinner, but the staff provided a list of eateries in the local area. I had a very good meal at the New American Grill. The breakfast menu at the...
The Inn is in a beautiful setting. The staff were very friendly and helpful. My room was spacious and a comfortable arm chair and good lamp provided a cozy place for R&R. The spacious common area & well kept grounds would be a very pleasant place to spend time with family and friends. I was advised in advance that the restaurant was not serving dinner, but the staff provided a list of eateries in the local area. I had a very good meal at the New American Grill. The breakfast menu at the...
Rita
Castle Hill Resort And Spa
Castle Hill Resort And SpaCavendish
10/10 Excellent
STAFF
I want to start by pointing out that the staff at the hotel were above and beyond PHENOMENAL, and I mean ALL THE STAFF.
I spent the weekend up there and got stuck with some car problems in a blizzard and dealt with everybody on the staff there. They were some of the nicest people I have ever dealt with in the hospitality industry.
When I say all the staff, I mean all the staff!
DAY 1. The plow guy helped me get my car out of a spot when my snow chain broke and I couldn’t move.
DAY 2...
STAFF
I want to start by pointing out that the staff at the hotel were above and beyond PHENOMENAL, and I mean ALL THE STAFF.
I spent the weekend up there and got stuck with some car problems in a blizzard and dealt with everybody on the staff there. They were some of the nicest people I have ever dealt with in the hospitality industry.
When I say all the staff, I mean all the staff!
DAY 1. The plow guy helped me get my car out of a spot when my snow chain broke and I couldn’t move.
DAY 2...
Steven
Kimpton Taconic Hotel by IHG
Kimpton Taconic Hotel by IHGManchester Village Historic District
10/10 Excellent
Very nice, upscale property with lovely interior design, attentive staff, and tasty dining options.
The not so good: Video entertainment. $27 for a 4 month old movie. Some in room maintenance issues. No in room luggage stands. Promoted free internet & parking however fine print states $33 resort fee pays for parking & internet. @$500 / night I would expect less nickel and dime.
Very nice, upscale property with lovely interior design, attentive staff, and tasty dining options.
The not so good: Video entertainment. $27 for a 4 month old movie. Some in room maintenance issues. No in room luggage stands. Promoted free internet & parking however fine print states $33 resort fee pays for parking & internet. @$500 / night I would expect less nickel and dime.
john
Four Columns Inn
Four Columns InnNewfane
10/10 Excellent
It was a short stay but an awesome one. Newfane is a quaint area. The room itself was beautiful. It was nice and quiet; didn’t hear others. Very clean. Would loved to have stayed longer. A little pricey but then it again it was a last minute booking and also peak foliage season.
It was a short stay but an awesome one. Newfane is a quaint area. The room itself was beautiful. It was nice and quiet; didn’t hear others. Very clean. Would loved to have stayed longer. A little pricey but then it again it was a last minute booking and also peak foliage season.
Nettie
The Weston
The WestonWeston
10/10 Excellent
The Weston is a spectacular small hotel. The restaurant is delicious and the staff go oabove and beyond to make your stay lovely.
The Weston is a spectacular small hotel. The restaurant is delicious and the staff go oabove and beyond to make your stay lovely.
astrid
The Jackson
The JacksonWest Woodstock
10/10 Excellent
Fantastic bed and breakfast tucked away from all the hustle.
Fantastic bed and breakfast tucked away from all the hustle.
Tiffany
Bromley View Inn
Bromley View InnBondville
10/10 Excellent
Great location for stratton and bromley mtns.
Great location for stratton and bromley mtns.
Rich
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Holiday Inn Club Vacations Mount Ascutney Resort by IHGBrownsville
10/10 Excellent
When I walked in the door I was dumbfounded with the size of the room, it was huge to call it a room does not do it justice. 2 stories, full living and dining room, you have to call it a villa, or a house I'd live in!
Clean comfortable, roomy, held 6 adults easily! Very new very modern, looked and smelled freshly renovated! Much more than I was expecting !
When I walked in the door I was dumbfounded with the size of the room, it was huge to call it a room does not do it justice. 2 stories, full living and dining room, you have to call it a villa, or a house I'd live in!
Clean comfortable, roomy, held 6 adults easily! Very new very modern, looked and smelled freshly renovated! Much more than I was expecting !
Jamie
On The River Inn
On The River InnWest Woodstock
10/10 Excellent
The pictures do not show how beautiful this property actually is. Looks 100 times better in person. They have a restaurant which is also very good. You don’t need to go anywhere else. The pool is a vibe after a long day of snowboarding. Recommend it 10/10. I will definitely go back again.
The pictures do not show how beautiful this property actually is. Looks 100 times better in person. They have a restaurant which is also very good. You don’t need to go anywhere else. The pool is a vibe after a long day of snowboarding. Recommend it 10/10. I will definitely go back again.
Ayleen
The Upper Pass Lodge at Magic Mountain
The Upper Pass Lodge at Magic MountainLondonderry
10/10 Excellent
Five stars for ambience, comfort, cleanliness. Very cozy common area and bar. Location is beautiful. Staff friendly.
I rated medium for condition as the place is old and clearly gets well used during ski season. HOWEVER, this is not ugly or bad as in a gross motel with broken stuff and dirt. The room was clean and nice and smelled fine, but the carpets were well worn and there is a lot of wear to the place in general. I did not want to leave too many stars on condition and have folks...
Five stars for ambience, comfort, cleanliness. Very cozy common area and bar. Location is beautiful. Staff friendly.
I rated medium for condition as the place is old and clearly gets well used during ski season. HOWEVER, this is not ugly or bad as in a gross motel with broken stuff and dirt. The room was clean and nice and smelled fine, but the carpets were well worn and there is a lot of wear to the place in general. I did not want to leave too many stars on condition and have folks...
Anonymous traveler
Inn on Putney Road
Inn on Putney RoadBrattleboro
10/10 Excellent
Superlative. Beautiful house and grounds with access to woodland trails and the river. Super friendly host and staff. Excellent breakfast. Best quality beds, linens and amenities.
Superlative. Beautiful house and grounds with access to woodland trails and the river. Super friendly host and staff. Excellent breakfast. Best quality beds, linens and amenities.
Victoria
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Village, A Vail Resorts PropertyJackson Gore Base Area
10/10 Excellent
Everything was not bad, due to Covid. So indoor Pool, sauna closed at 6pm, bar at 9! Big problem was with the room, they put me in totally different room as shown on the pictures, but big thanks guest check-in personal, they fix this problem.
Everything was not bad, due to Covid. So indoor Pool, sauna closed at 6pm, bar at 9! Big problem was with the room, they put me in totally different room as shown on the pictures, but big thanks guest check-in personal, they fix this problem.
Volodymyr N.
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 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. Stone Hearth Inn and Eatery: Resort with 4 restaurants. Enjoy the 2 bars, free WiFi, and free valet parking. Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area: B&B with restaurant. Enjoy the bar, free WiFi, and free parking. Woodstock Inn & Resort: Resort with restaurant. Enjoy the bar, free WiFi, and full-service spa. The Jackson : 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.