Title: Book the Best Hotels with BARS in Pittsfield in 2026 | 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 $166 - ![](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 ## Our top choices for Pittsfield hotels with a bar ![Exterior](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/ec2b6d3b.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) ![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) ### Brandon Inn [](https://www.expedia.ca/Brandon-Hotels-Brandon-Inn.h25184647.Hotel-Information) Brandon 8.8/10 Excellent (569) "Enjoyed our stay at the Brandon Inn very much!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lesley CA $150 CA $166 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Brandon-Hotels-Brandon-Inn.h25184647.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/15d4fef0.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/1000000/10000/4700/4621/6cdf9844.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 [](https://www.expedia.ca/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.Hotel-Information) Rutland 8.0/10 Very good (1005) "Clean rooms and polite workers. Try to stay there every time we go to Vermont." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $196 CA $216 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/970000/970000/969917/9add75ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard Middlebury [](https://www.expedia.ca/Middlebury-Hotels-Courtyard-Middlebury.h969917.Hotel-Information) Middlebury 8.8/10 Excellent (548) "Laundry service was efficient and parking was easy " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Agnes CA $171 CA $188 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Middlebury-Hotels-Courtyard-Middlebury.h969917.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) ![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) ### Mountain Meadows Lodge [](https://www.expedia.ca/Killington-Hotels-Mountain-Meadows-Lodge.h894095.Hotel-Information) Killington 9.4/10 Exceptional (184) "Staff was amazing! They made the stay even better with their hospitality and overall service. I recommend this Lodge to anyone looking to go to Killington who wants a fun and relaxing stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaden CA $284 CA $347 total includes taxes & fees Jan 20 - Jan 21, 2026 [](https://www.expedia.ca/Killington-Hotels-Mountain-Meadows-Lodge.h894095.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) ![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) ### North Star Lodge and Resort [](https://www.expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) Killington 8.6/10 Excellent (1007) "Spotless room also very accommodating and friendly! Loved our short stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Candace [](https://www.expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.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) ![Hallway](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/8d6bfa64.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) ![Breakfast area](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/cd26b573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### On The River Inn [](https://www.expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) West Woodstock 9.4/10 Exceptional (1002) "Rearaurant staff was top notch. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel [](https://www.expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/6aabd3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Jackson [](https://www.expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) West Woodstock 9.8/10 Exceptional (258) "The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abby [](https://www.expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![The Jewel | Living area](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/53dd6cd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mountain Aire Lodge | Private kitchen](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/15f330b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Foley Farmhouse | Living area](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/281effc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, beach towels, kayaking](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/80a87dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mountain Top Inn & Resort [](https://www.expedia.ca/Chittenden-Hotels-The-Mountain-Top-Inn-Resort.h9673261.Hotel-Information) Chittenden 9.0/10 Wonderful (99) "Room was comfy and clean. The view from the window was gorgeous. The whole resort was so quaint, warm and beautiful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ping CA $444 CA $484 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Chittenden-Hotels-The-Mountain-Top-Inn-Resort.h9673261.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/2000000/1110000/1102600/1102506/5da3617c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1110000/1102600/1102506/08318750.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/2000000/1110000/1102600/1102506/9a5774d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, Irish cuisine](https://images.trvl-media.com/lodging/2000000/1110000/1102600/1102506/e7023543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Summit Lodge [](https://www.expedia.ca/Killington-Hotels-Summit-Lodge.h1102506.Hotel-Information) Killington 8.6/10 Excellent (402) "Good location and close to ski area. Good free breakfast makes stay nicer. Staff are nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) RAYMOND CA $237 CA $261 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Killington-Hotels-Summit-Lodge.h1102506.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1160000/1154000/1153997/86a78166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 Bedroom Master Suite | Shared kitchen](https://images.trvl-media.com/lodging/2000000/1160000/1154000/1153997/6ca20d37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1160000/1154000/1153997/8a3ab1de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1160000/1154000/1153997/bc79e27c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Snowed Inn [](https://www.expedia.ca/Killington-Hotels-Snowed-Inn.h1153997.Hotel-Information) Killington 9.8/10 Exceptional (374) "A wonderful hotel. The atmosphere is warm and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fevzi CA $323 CA $391 total includes taxes & fees Jan 21 - Jan 22, 2026 [](https://www.expedia.ca/Killington-Hotels-Snowed-Inn.h1153997.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=2026-01-13&endDate=2026-01-14®ionId=184066&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Pittsfield Hotel Reviews ![The Mountain Inn at Killington](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441_y.jpg) ### The Mountain Inn at Killington 10/10 Excellent "It was our first time staying here and the experience was excellent. All the staff were very kind and helpful. The hotel’s location is excellent, and the breakfast and restaurant food were delicious. 100% recommended." [](https://expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![North Star Lodge and Resort](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/0612ebf1_y.jpg) ### North Star Lodge and Resort 10/10 Excellent "Classic resort lodge with comfortable soft beds and an easy family run vibe. Perfect overnight or weekend home for exploring Killington. Pool and bar, and right on Killington Rd. The Foundry at Summit Pond is a terrific bistro and just 2 min down the path. My son and I loved it. " [](https://expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![Killington Mountain Lodge, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/403a8548_y.jpg) ### Killington Mountain Lodge, Tapestry Collection by Hilton 10/10 Excellent "It was great " [](https://expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![Comfort Inn Rutland - Killington](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/15d4fef0_y.jpg) ### Comfort Inn Rutland - Killington 10/10 Excellent "Super clean and staff was very accommodating when I needed to change to a larger room. Great stay!" [](https://expedia.ca/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.Hotel-Information) ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg) ### On The River Inn 10/10 Excellent "Nice experience. Great location, good property, excellent service and care taking" [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Mountain Meadows Lodge](https://images.trvl-media.com/lodging/1000000/900000/894100/894095/7995d81d_y.jpg) ### Mountain Meadows Lodge 10/10 Excellent "Staff was courteous and had my room ready to go and let on hand on minutes. Room is clean, spacious, and updated. They use text for frequent updates. A great place in close proximity to the mountain." [](https://expedia.ca/Killington-Hotels-Mountain-Meadows-Lodge.h894095.Hotel-Information) ![Days Inn by Wyndham Rutland/Killington Area](https://images.trvl-media.com/lodging/1000000/890000/889600/889570/2b102593_y.jpg) ### Days Inn by Wyndham Rutland/Killington Area 10/10 Excellent "Best Pool and hot breakfast. " [](https://expedia.ca/Rutland-Hotels-Days-Inn-By-Wyndham-RutlandKillington-Area.h889570.Hotel-Information) ![Best Western Inn & Suites Rutland-Killington](https://images.trvl-media.com/lodging/1000000/20000/16500/16411/9898f616_y.jpg) ### Best Western Inn & Suites Rutland-Killington 10/10 Excellent "Very nice and friendly welcome from Stephen! Room was very clean and quiet. Nice set up with tv , microwave and fridge. Bed was very comfortable. Breakfast that was included was far beyond expectation with great choices and added options for each selection. Breakfast area was cozy and welcoming with the fireplace stove on the very cold days we were visiting. Stayed here since it was close to family. The fresh baked cookies at the end of the day were another delightful treat to our stay. Any staff we encountered during our stay were always very friendly and helpful. Would definitely stay here again when we are back in the area." [](https://expedia.ca/Rutland-Hotels-Best-Western-Inn-Suites-Rutland-Killington.h16411.Hotel-Information) ![Mountain Sports Inn](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/7b3b252e_y.jpg) ### Mountain Sports Inn 10/10 Excellent "Clean room and helpful staff, definitely worth the price." [](https://expedia.ca/Killington-Hotels-Mountain-Sports-Inn.h1339833.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Pittsfield? ### What are the best hotels with bars in Pittsfield? ### What is there to do in Pittsfield? ### When is the best time to visit Pittsfield? ### How can I get to Pittsfield and around the area? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Killington ](https://www.expedia.ca/4Star-Killington-Hotels.s40-0-d10780.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Burlington ](https://www.expedia.ca/Burlington-Hotels-Adults-Only-Resorts.0-0-d601763-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Burlington ](https://www.expedia.ca/Burlington-Hotels-Couples-Resorts-Hotels.0-0-d601763-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Green Hotels in Burlington ](https://www.expedia.ca/Burlington-Hotels-Green-Sustainable.0-0-d601763-tGreenSustainable.Travel-Guide-Filter-Hotels) - 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