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://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 Pittsfield, VT from CA $159 ![](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/1000000/10000/4700/4621/62720c61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/5b9c435c.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) ### Comfort Inn Rutland - Killington Rutland 8.0/10 Very good (1022) "Cleanliness, convenient location with my EV vehicle charging station nearby & dining options were great." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaime CA $154 CA $169 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.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) ![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) ![Game room](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/72849c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/3cca622a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mountain Inn at Killington Killington 9.2/10 Wonderful (920) "Nice accommodations, very inviting and friendly staff. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott CA $177 CA $204 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.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/26000000/25190000/25184700/25184647/869870f6.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) ![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 8.6/10 Excellent (546) "Quaint hotel…..love the history " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly CA $155 CA $171 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Brandon-Hotels-Brandon-Inn.h25184647.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) ![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/1000000/190000/181400/181337/91483dc1.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. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Yinghua CA $184 CA $203 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Family Suite, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/528a7f5b.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) ![Family Suite, 1 Bedroom | Private kitchen](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/29250062.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/e090e64b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### On The River Inn West Woodstock 9.4/10 Exceptional (1004) "Great location, very quiet with good breakfast choices. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $252 CA $328 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.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) ![Point of interest](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/f6266999.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) ![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 (1017) "Great place to stay" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary CA $145 CA $159 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.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) ![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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/894100/894095/7d78fd71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Meadows Lodge Killington 9.4/10 Exceptional (158) "Lovely property and the staff members were extremely friendly" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine CA $238 CA $297 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Killington-Hotels-Mountain-Meadows-Lodge.h894095.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) ![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) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1590000/1581700/1581667/12bb1168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Neshobe River Brandon 9.4/10 Exceptional (16) "Great little BAnd B just outside town. Shares property with a brewery and also offers a small food menu for dinner Fantastic view of the golf course 5 th hole Great hospitality and crazy good breakfast " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Keith [](https://www.expedia.ca/Brandon-Hotels-Inn-At-Neshobe-River.h1581667.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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/970000/970000/969917/639f7401.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) ![Room, 1 King Bed with Sofa bed, Fireplace](https://images.trvl-media.com/lodging/1000000/970000/970000/969917/60c0d212.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard Middlebury Middlebury 8.8/10 Excellent (532) "Great hotel, fairly centered , great staff!" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Angelo CA $188 CA $207 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Middlebury-Hotels-Courtyard-Middlebury.h969917.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) ![Reception](https://images.trvl-media.com/lodging/101000000/100890000/100885900/100885865/33f05a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grey Bonnet Inn Killington 7.8/10 Good (61) "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!" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan CA $207 CA $228 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Killington-Hotels-Grey-Bonnet-Inn.h100885865.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=2025-11-01&endDate=2025-11-02®ionId=184066&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Pittsfield Hotel Reviews ![Mountain Sports Inn](//images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/7b3b252e_y.jpg) ### Mountain Sports Inn 10/10 Excellent "This is a great place to stay. Attentive staff, easy parking, lots of options on the continental breakfast. " [](https://expedia.ca/Killington-Hotels-Mountain-Sports-Inn.h1339833.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) ![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 "Clean room , view of the golf area , very good breakfast." [](https://expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![Cortina Inn](//images.trvl-media.com/lodging/1000000/30000/27000/27000/aa6e8386_y.jpg) ### Cortina Inn 8/10 Good "All fine " [](https://expedia.ca/Rutland-Hotels-Cortina-Inn.h27000.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 "Staff very friendly, helpful and welcoming." [](https://expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.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 "Great 👍 " [](https://expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![The Jackson ](//images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg) ### The Jackson 10/10 Excellent "The staff were incredible, so friendly and welcoming. Each night they served wine, cheese and crackers. The overall atmosphere and hospitality was amazing. We hated to leave." [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.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 "The staff was pleasant and we enjoyed our stay. We loved the pool, hot tub and breakfast in the morning! " [](https://expedia.ca/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.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 "Welcoming staff. No complaints" [](https://expedia.ca/Rutland-Hotels-Days-Inn-By-Wyndham-RutlandKillington-Area.h889570.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Pittsfield? > Pittsfield features 40 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 Vermont Ski and Snowmobiling House](https://www.expedia.ca/Pittsfield-Hotels-Newly-Built-Killington-Vermont-Ski-House.h32033631.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. [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. [Woodstock Inn & Resort](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. [The Shire Woodstock](https://www.expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.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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