Title: Book the Best Hotels with BARS in Chester in 2025 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d89014.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d89014.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d89014.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d89014.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Bar in Chester, VT from CA $110 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chester Hotels with Bar ## Top Chester Hotels with Bar ![Garden](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/662925ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/0b7fdcd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/c887af2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/69a574aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fullerton Inn Chester Depot 8.2/10 Very good (394) "Lovely stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine CA $181 CA $197 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Chester-Hotels-Fullerton-Inn.h15845368.Hotel-Information) ![Lounge](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/85d1c6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/c0073409.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room, 1 Double Bed, 1 King Bed, 1 Twin Bed](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/4ee226d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/c28fd1d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bromley View Inn Bondville 9.2/10 Wonderful (392) "Great place and close to everything " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debra CA $116 CA $128 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bennington-Hotels-Bromley-View-Inn.h1502963.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/c6f78187.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/4b2f1194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/e0c2a7a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Equinox Golf Resort & Spa Manchester 7.4/10 Good (553) "Beautiful hotel! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sarah CA $142 CA $230 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![Indoor spa tub](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/a75b732a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Yoga](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/3d6e59aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/7c69c2ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/4e3f46ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Bear Lodge at Stratton Mountain Resort Stratton 7.6/10 Good (927) "What a great, cozy place! Definitely would stay here again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Naomi CA $184 CA $223 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ![Premium bedding, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-4a5edcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2557x3y3-db499e38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-dbaacfef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Keene Hotel Keene 8.4/10 Very good (1023) "Great staff, clean room, nice breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DORTHY CA $210 CA $228 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Exclusive Suite, Multiple Beds, Kitchenette, Mountain View](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/6e934e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/80ab5ea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Room, 1 Double Bed](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/99257ee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/31952972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Upper Pass Lodge at Magic Mountain Londonderry 8.2/10 Very good (676) "If this property was updated it would be a wonderful place to stay but as is it’s like a very old motel. I would not stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathy CA $100 CA $110 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Londonderry-Hotels-The-Upper-Pass-Lodge-At-Magic-Mountain.h1445790.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/91483dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/6aabd3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/e0958349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Jackson West Woodstock 9.8/10 Exceptional (237) "Excellent Vintage style B&B. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yinghua CA $184 CA $202 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/7bc7321f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/30a7f959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/b043b966.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![American cuisine](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/9cdfa045.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Keene Downtown Keene 8.8/10 Excellent (1002) "Lovely hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ronald CA $220 CA $239 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/125b9e2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Apartment, 2 Bedrooms, Courtyard View | Private kitchen](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/85e707a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/2bbb4b02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### On The River Inn West Woodstock 9.4/10 Exceptional (1005) "Nice property. Good location and very friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bertrand CA $251 CA $328 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/bb7b6824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room with Garden View | Living area](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/074a9a47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/aa061d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room with Spa Bath](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/ad9a6e84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Weathersfield Perkinsville 9.8/10 Exceptional (68) "Comfortable room and tasty dinner. Very well run." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew CA $318 CA $398 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Perkinsville-Hotels-The-Inn-At-Weathersfield.h1154949.Hotel-Information) 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](https://expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03®ionId=89014&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![The Equinox Golf Resort & Spa](//images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg) ### The Equinox Golf Resort & Spa 10/10 Excellent "Beautiful property, wonderful views, loved our room, loved the huge indoor heated pool and the outdoor jacuzzi. Bar staff, food and drinks were fantastic at the on site bar/restaurant The Falcon, shout out to Maddie for being awesome. Bummer the steal house was closed the entirety of our stay (Sun-Weds), but what are ya gonna do. Would recommend, and would love to return next autumn. " [](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![Latchis Hotel](//images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Is a great historic building with great charm. Hope to stay there again soon." [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![Best Western Plus Keene Hotel](//images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg) ### Best Western Plus Keene Hotel 10/10 Excellent "The on-site restaurant named Tempestas was excellent and a huge plus for our 3-night stay. We ate there every night and were pleased with the food, service, atmosphere and the prices were reasonable. On a broader note, the hotel was nice, staff very helpful and I should mention that the breakfast one of the best I've had on 3 continents, aided by a hostess who was friendly and took lots of pride in serving hot food and keeping the food and coffee fresh." [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Jackson Gore Village](//images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg) ### Jackson Gore Village 10/10 Excellent "The staff truly made the experience stand out. From check-in to check-out, everyone I interacted with was professional, friendly, and genuinely welcoming. " [](https://expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information) ![Mount Snow Grand Summit Resort](//images.trvl-media.com/lodging/1000000/670000/663200/663170/effe663b_y.jpg) ### Mount Snow Grand Summit Resort 10/10 Excellent "Amazing 2 big hot tubes and warm swim pool on the open air !!! A lot of restaurants around and Beautiful nature! But chairlifts was closed- so check availability " [](https://expedia.ca/West-Dover-Hotels-Mount-Snow-Grand-Summit-Resort.h663170.Hotel-Information) ![Colonial Motel And Spa](//images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg) ### Colonial Motel And Spa 10/10 Excellent "Clean, spacious room. Seemed to have been updated " [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![Pointe at Castle Hill Resort](//images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "The place was out slightly out of town so it was quiet. " [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Woodstock Inn & Resort](//images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "It's a lovely property and the staff are very nice. They seemed a but overwhelmed (or short staffed). Our room wasn't serviced because they didn't arrive until very late in the day each day. By that time, we were in the room preparing for the evening. We just traded out our towels for fresh ones and got the trash emptied. That is all we really needed but it was a bit surprising in this hotel." [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![Kimpton Taconic Hotel by IHG](//images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/72cb9377_y.jpg) ### Kimpton Taconic Hotel by IHG 10/10 Excellent "The is was our first trip to Manchester. What a great town! The hotel was lovely- easy parking, quiet, and quaint. The staff at the front desk were so helpful ! You could walk to town but it would be about a 20 min adventure… make sure you go to the North field book store~ wonderful!! And we had coffee and egg sandwich at their coffee shop around the corner." [](https://expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information) ## 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: [The Shire Woodstock](https://www.expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information): Resort with 4 restaurants. Enjoy the 2 bars, free WiFi, and free valet parking. [Woodstock Inn & Resort](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information): Hotel with 4 restaurants. Enjoy the 2 bars, free parking, and seasonal outdoor pool. [The Equinox Golf Resort & Spa](https://www.expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information): Hotel with 2 restaurants. Enjoy the bar, free WiFi, and free parking. [Jackson Gore Village](https://www.expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. [Pointe at Castle Hill Resort](https://www.expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information): Hotel with restaurant. Enjoy the bar, seasonal outdoor pool, and breakfast. ### What is there to do in Chester? > To experience the area's highlights, consider visiting Grafton Historical Society, Vermont Country Store, and Plummer's Sugar House, 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. 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