Title: The Best Pittsfield, VT Chalets from $440 | Expedia.com [Pittsfield Travel Guide](https://expedia.com/Pittsfield.dx184066)[Hotels in Pittsfield](https://expedia.com/Pittsfield-Hotels.d184066.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.com/Pittsfield-Vacation-Rentals.d184066.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.com/Cheap-Flights-To-Pittsfield.d184066.Travel-Guide-Flights)[Car Rentals in Pittsfield](https://expedia.com/Car-Rentals-In-Pittsfield.d184066.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.com/Pittsfield.d184066.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pittsfield chalets ![Exterior](https://images.trvl-media.com/lodging/64000000/63030000/63026900/63026865/d42e6390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/64000000/63030000/63026900/63026865/7e228bd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/64000000/63030000/63026900/63026865/a11e6e92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63030000/63026900/63026865/87d01392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dreamy Artist Chalet in Secluded Historic Village [](https://www.expedia.com/Warren-Hotels-Dreamy-Artist-Chalet-In-Secluded-Historic-Village.h63026865.Hotel-Information) East Warren 9.4/10 Exceptional (11 reviews) "Everything was beautiful. But for sure needs new mattress and pillows. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeanette R. $393 nightly $440 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Warren-Hotels-Dreamy-Artist-Chalet-In-Secluded-Historic-Village.h63026865.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/48be0320.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/98a04e79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/b2a8b57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/c33b35a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gnome Home Mountain Ski Chalet w/Sauna Killington [](https://www.expedia.com/Stockbridge-Hotels-Gnome-Home-Mountain-Ski-Chalet-WSauna-Killington.h87515446.Hotel-Information) Stockbridge 10/10 Exceptional (4 reviews) "Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gerald S. $542 nightly $575 total Mar 3 - Mar 4 Total with taxes and fees [](https://www.expedia.com/Stockbridge-Hotels-Gnome-Home-Mountain-Ski-Chalet-WSauna-Killington.h87515446.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123270000/123267000/123266945/e9ee5480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123270000/123267000/123266945/fa430ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123270000/123267000/123266945/0626f3ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/124000000/123270000/123267000/123266945/45bdedf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub [](https://www.expedia.com/Killington-Hotels-Fabulous-4-Bedroom-Chalet-In-Tranquil-Killington-Getaway-With-Gorgeous-Hot-Tub.h123266945.Hotel-Information) North Sherburne 8.0/10 Very Good (5 reviews) $512 nightly $578 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Killington-Hotels-Fabulous-4-Bedroom-Chalet-In-Tranquil-Killington-Getaway-With-Gorgeous-Hot-Tub.h123266945.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/102000000/101010000/101007200/101007141/8a8dfe15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101010000/101007200/101007141/9783b75f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101010000/101007200/101007141/e67cd3ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/102000000/101010000/101007200/101007141/086d7028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Handcrafted Log Home Near Sugarbush & Mad River Glen • Walk to Blueberry Lake [](https://www.expedia.com/Warren-Hotels-Authentic-Log-Home-In-Warren-Ski-Town-Mountain-Biking-Short-Walk-To-Lake.h101007141.Hotel-Information) East Warren 10/10 Exceptional (3 reviews) "The house is amazing. The hosts clearly love it, and it shows in how well it is set up and stocked. Highly recommended." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Greg E. $600 nightly $672 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Warren-Hotels-Authentic-Log-Home-In-Warren-Ski-Town-Mountain-Biking-Short-Walk-To-Lake.h101007141.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/97000000/96030000/96029800/96029719/6b02a563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dishwasher, electric kettle, spices, dining tables](https://images.trvl-media.com/lodging/97000000/96030000/96029800/96029719/31ea8443.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96030000/96029800/96029719/c588c075.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/97000000/96030000/96029800/96029719/8e8c7e4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Overlook - Hot Tub, Game Room, 5min to MTN [](https://www.expedia.com/Killington-Hotels-The-Overlook-Hot-Tub.h96029719.Hotel-Information) Killington 10/10 Exceptional (2 reviews) "We stayed at the overlook for a family ski trip. It was the perfect place for our family of 4 with 2 young kids. The house was well appointed and what we expected, our hosts communicated well and it was an easy drive to killington mountain every day to ski." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matt F. $1,171 nightly $1,323 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Killington-Hotels-The-Overlook-Hot-Tub.h96029719.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89990000/89982100/89982066/400cdd0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89990000/89982100/89982066/1e901d44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/90000000/89990000/89982100/89982066/ecac89c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89990000/89982100/89982066/a250ff08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BearHaus-Fireplace, HUGE indoor Hot Tub, Sleeps 14 [](https://www.expedia.com/Killington-Hotels-BearHaus-New-Reno.h89982066.Hotel-Information) Killington 9.6/10 Exceptional (5 reviews) "Great property - excellent hosts. Close to mountain and restaurants" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric D. $943 nightly $1,066 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Killington-Hotels-BearHaus-New-Reno.h89982066.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107260000/107257700/107257611/f34d73ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/108000000/107260000/107257700/107257611/68751e99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/108000000/107260000/107257700/107257611/2171e7a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107260000/107257700/107257611/bdccca36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals. [](https://www.expedia.com/Killington-Hotels-West-Park-Chalet-At-Killington-Great-For-Groups-Hot-Tub.h107257611.Hotel-Information) Killington 8.8/10 Excellent (3 reviews) "Great location and ski house layout. Pool Table Rec Room, TV Rec Room and Hot Tub." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rob S. $1,041 nightly $1,176 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Killington-Hotels-West-Park-Chalet-At-Killington-Great-For-Groups-Hot-Tub.h107257611.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/108000000/107230000/107229500/107229459/7e8d3365.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, offices](https://images.trvl-media.com/lodging/108000000/107230000/107229500/107229459/ecbb54f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107230000/107229500/107229459/720c9070.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107230000/107229500/107229459/de4ddd36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace. [](https://www.expedia.com/Killington-Hotels-Bigelow-Chalet-At-Killington-8BR45-BA-Pet-Friendly-Home-W-Hot-Tub.h107229459.Hotel-Information) Killington 8.0/10 Very Good (2 reviews) "Awesome property and very responsive staff! Highly recommended. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony P. $1,344 nightly $1,519 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Killington-Hotels-Bigelow-Chalet-At-Killington-8BR45-BA-Pet-Friendly-Home-W-Hot-Tub.h107229459.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.com/Hotel-Search?startDate=2026-02-23&endDate=2026-02-24®ionId=184066&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=VACATION_HOME) Condos [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=CONDO) Cottages [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=COTTAGE) Apartments [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=APARTMENT) Chalets [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=CHALET) Villas [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=VILLA) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Chalets.d184066-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Chalets.d184066-aaChalets.Travel-Guide-Accommodation) ## 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 "The staff could not have been more accommodating. From the front desk to the shuttle drivers, to the wait staff in the restaurant, they were all friendly, helpful and pleasant." [](https://expedia.com/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Great room, lovely view and a wonderful town " [](https://expedia.com/Woodstock-Hotels-The-Shire-Woodstock.h10453651.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 "Staff was helpful and room was clean" [](https://expedia.com/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![Turn of River Lodge](https://images.trvl-media.com/lodging/19000000/18550000/18540700/18540657/e79916d3_y.jpg) ### Turn of River Lodge 10/10 Excellent "Yes " [](https://expedia.com/Killington-Hotels-Turn-Of-River-Lodge.h18540657.Hotel-Information) ![Summit Lodge](https://images.trvl-media.com/lodging/2000000/1110000/1102600/1102506/5da3617c_y.jpg) ### Summit Lodge 10/10 Excellent "Reasonable clean nice place to stay" [](https://expedia.com/Killington-Hotels-Summit-Lodge.h1102506.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 "Great staff, clean hotel very happy :) " [](https://expedia.com/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 "Staff very nice and professional. Hotel clean" [](https://expedia.com/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Brandon Inn](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/ec2b6d3b_y.jpg) ### Brandon Inn 10/10 Excellent "The hotel was beyond charming. My car club takes a trip to Vermont every year. And we will be changing our itinerary. So that we can stay at the Brandon Inn For the duration of our trip, rather than just the return leg. We absolutely loved it" [](https://expedia.com/Brandon-Hotels-Brandon-Inn.h25184647.Hotel-Information) ![Hampton Inn Rutland](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522922/f4f05fc2_y.jpg) ### Hampton Inn Rutland 10/10 Excellent "This was a wonderful hotel! Very clean, lots of parking, close to shopping/restaurants, friendly staff and great amenities. I would highly recommend if you were staying in the Rutland area!" [](https://expedia.com/Rutland-Hotels-Hampton-Inn-Rutland.h1522922.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Chalets information | Number of reviews | 30 | | ----------------- | ---------- | | Accommodation | 33 Chalets | | Lowest Price | $440 | | Highest Price | $1,519 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [B&B in Stockbridge ](https://www.expedia.com/Stockbridge-Bed-And-Breakfast.d6357893-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Stockbridge ](https://www.expedia.com/Stockbridge-Chalets.d6357893-aaChalets.Travel-Guide-Accommodation) - [Cabin Rentals in Stockbridge ](https://www.expedia.com/Stockbridge-Cabins.d6357893-aaCabins.Travel-Guide-Accommodation) - [Stockbridge Hotels ](https://www.expedia.com/Stockbridge-Hotels.d6357893.Travel-Guide-Hotels) - [Pet-friendly Hotels in Stockbridge ](https://www.expedia.com/Stockbridge-Hotels-Pet-Friendly-Hotel.0-0-d6357893-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - 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