Title: Book the Best Hotels with BARS in Pittsfield in 2025 | Expedia.ca [Pittsfield Travel Guide](https://expedia.ca/Pittsfield.dx184066)[Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d184066.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d184066.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.ca/Cheap-Flights-To-Pittsfield.d184066.Travel-Guide-Flights)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d184066.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d184066.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/bar.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Bar in Pittsfield, VT from CA $170 - ![](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 Pittsfield Hotels with Bar ## Top Pittsfield Hotels with Bar ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/15d4fef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/6cdf9844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/325364db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/62720c61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Rutland - Killington Rutland 8.0/10 Very good (1003) "Clean, great steak house by the hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caridad CA $155 CA $170 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/ec2b6d3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/69209bc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/869870f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/0a464c94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brandon Inn Brandon 8.8/10 Excellent (554) "Quaint hotel…..love the history " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly CA $155 CA $171 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Brandon-Hotels-Brandon-Inn.h25184647.Hotel-Information) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/72849c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/374f8e02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/18beef69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mountain Inn at Killington Killington 9.2/10 Wonderful (934) "Excellent hotel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristan CA $169 CA $195 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![Lake view](https://images.trvl-media.com/lodging/1000000/900000/894100/894095/7995d81d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served](https://images.trvl-media.com/lodging/1000000/900000/894100/894095/f9d7db28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Farmhouse Thundering Brook | Living area](https://images.trvl-media.com/lodging/1000000/900000/894100/894095/537271c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Farmhouse Thundering Brook](https://images.trvl-media.com/lodging/1000000/900000/894100/894095/d33b7a82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Meadows Lodge Killington 9.4/10 Exceptional (168) "Lovely property and the staff members were extremely friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine CA $231 CA $290 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Killington-Hotels-Mountain-Meadows-Lodge.h894095.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/970000/970000/969917/587431c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/970000/970000/969917/9add75ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/970000/970000/969917/b250ecb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/970000/970000/969917/639f7401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard Middlebury Middlebury 8.8/10 Excellent (535) "Great hotel, fairly centered , great staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angelo CA $176 CA $194 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Middlebury-Hotels-Courtyard-Middlebury.h969917.Hotel-Information) ![Standard Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/0612ebf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/bed9fca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/17fcad53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/db156eb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Star Lodge and Resort Killington 8.6/10 Excellent (1002) "Was perfect for our one night stay " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Ian CA $183 CA $201 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.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) ![Garden](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/5f513e0c.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 (241) "Great stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Romulo [](https://www.expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/c49d548b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/cd26b573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### On The River Inn West Woodstock 9.4/10 Exceptional (1018) "The setting was beautiful, great amenities on site, complementary hot breakfast was delicious, lots of storage in the room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah CA $272 CA $351 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/101000000/100890000/100885900/100885865/775058e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/101000000/100890000/100885900/100885865/5cfd7092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/101000000/100890000/100885900/100885865/5257ce1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/101000000/100890000/100885900/100885865/e2d321f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grey Bonnet Inn Killington 7.8/10 Good (62) "The bar was closed so that was a bummer. The room was clean, parking was right by my room and the location of the property is right next to the road I was traveling on. Somehow it was still very quiet!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan CA $198 CA $218 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Killington-Hotels-Grey-Bonnet-Inn.h100885865.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1590000/1581700/1581667/354bde1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1590000/1581700/1581667/2e7ed595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living room](https://images.trvl-media.com/lodging/2000000/1590000/1581700/1581667/1700a7ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Rose Room](https://images.trvl-media.com/lodging/2000000/1590000/1581700/1581667/9cce230c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Neshobe River Brandon 9.4/10 Exceptional (16) "Beautiful upon arrival we were greeted by the host. She took plenty of time to show us around the property and explain how the bed-and-breakfast works and all the details of the winery brewery excellent day! Days of day." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) shawn CA $267 CA $293 total includes taxes & fees Dec 6 - Dec 7 [](https://www.expedia.ca/Brandon-Hotels-Inn-At-Neshobe-River.h1581667.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=2025-11-21&endDate=2025-11-22®ionId=184066&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Pittsfield Hotel Reviews ![The Jackson ](//images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg) ### The Jackson 10/10 Excellent "Loved the casual, comfortable, easy atmosphere. Homey and welcoming but never overbearing. Staff were all wonderful and personable. " [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Killington Mountain Lodge, Tapestry Collection by Hilton](//images.trvl-media.com/lodging/1000000/110000/103700/103640/403a8548_y.jpg) ### Killington Mountain Lodge, Tapestry Collection by Hilton 10/10 Excellent "Room was spotless and comfortable. Dog friendly, hassle free stay. Cleanliness was top tier, and staff was fantastic!" [](https://expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![The Mountain Inn at Killington](//images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441_y.jpg) ### The Mountain Inn at Killington 10/10 Excellent "Excellent hotel. " [](https://expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![Comfort Inn Rutland - Killington](//images.trvl-media.com/lodging/1000000/10000/4700/4621/15d4fef0_y.jpg) ### Comfort Inn Rutland - Killington 10/10 Excellent "Quiet and low key. " [](https://expedia.ca/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.Hotel-Information) ![On The River Inn](//images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/528a7f5b_y.jpg) ### On The River Inn 10/10 Excellent "The restaurant was very nice. Great service. Delicious food." [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Woodstock Inn & Resort](//images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "The staff were so welcoming and friendly! When we got engaged they all cheered for us and were so sweet!" [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![Days Inn by Wyndham Rutland/Killington Area](//images.trvl-media.com/lodging/1000000/890000/889600/889570/2b102593_y.jpg) ### Days Inn by Wyndham Rutland/Killington Area 10/10 Excellent "The breakfast selection was good with eggs, sausage, toast, bagels, waffles, fresh fruit, cereal, yogurt. The room was clean however the bathroom could use updating but was adequate. " [](https://expedia.ca/Rutland-Hotels-Days-Inn-By-Wyndham-RutlandKillington-Area.h889570.Hotel-Information) ![North Star Lodge and Resort](//images.trvl-media.com/lodging/1000000/190000/185900/185873/0612ebf1_y.jpg) ### North Star Lodge and Resort 10/10 Excellent "The hotel is located up a hill in a nice town, and is very peaceful and quiet. The room was clean. I have no complaints. I would definitely stay here again." [](https://expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![Best Western Inn & Suites Rutland-Killington](//images.trvl-media.com/lodging/1000000/20000/16500/16411/9898f616_y.jpg) ### Best Western Inn & Suites Rutland-Killington 10/10 Excellent "Good food and selection" [](https://expedia.ca/Rutland-Hotels-Best-Western-Inn-Suites-Rutland-Killington.h16411.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Pittsfield? > Pittsfield features 39 properties to choose from, and likely many will have a bar where you can enjoy a beer after a day out and about exploring. While you're here, you can check out Green Mountain National Forest and Roger Clark Memorial Central Library. ### What are the best hotels with bars in Pittsfield? > Below are some of top hotels with bars in and around Pittsfield: [Killington Mountain Lodge, Tapestry Collection by Hilton](https://www.expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information): Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. [Comfort Inn Rutland - Killington](https://www.expedia.ca/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.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 restaurant. Enjoy the bar, free breakfast, and free WiFi. [The Shire Woodstock](https://www.expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. [The Mountain Inn at Killington](https://www.expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information): B&B with restaurant. Enjoy the bar, free WiFi, and free parking. ### What is there to do in Pittsfield? > Consider a visit to Green Mountain National Golf Course, Gifford Woods State Park, and Pico Mountain at Killington Ski Resort, and then find a cozy spot for a nightcap. Other places to see include Green Mountain National Forest and Roger Clark Memorial Central Library. ### When is the best time to visit Pittsfield? > Visiting local bars in Pittsfield is more fun when you know what the weather holds. These temperatures and rainfall averages can help you determine the best time for bar hopping. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Pittsfield are January, March, February, and December, with each month seeing an average of 10 inches of snowfall. ### How can I get to Pittsfield and around the area? > Here are some of your transportation choices in and around Pittsfield: Fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is located 18.1 mi (29.2 km) from the city center. You can also search for flights into Lebanon, NH (LEB-Lebanon Municipal), which is 27.2 mi (43.7 km) away. 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