Title: Browse the Best Pittsfield Resorts from CA $450 | 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) # Search Resort Hotels in Pittsfield from CA $450 ![](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 prices for these dates Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Pittsfield Resorts ![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) ![The Jewel ](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/369f7f98.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) ![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) ### The Mountain Top Inn & Resort Chittenden 9.0/10 Wonderful (93) "We had a great time! Gorgeous view and everybody was super friendly and helpful!" CA $413 CA $450 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chittenden-Hotels-The-Mountain-Top-Inn-Resort.h9673261.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/fd07d4fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/cd86c3e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/3e81c990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodstock Inn & Resort Woodstock 9.2/10 Wonderful (538) "Beautiful hotel!! The staff, room, and spa were fantastic!!" CA $573 CA $692 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.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=2025-10-27&endDate=2025-10-28®ionId=184066&adults=2&lodging=HOTEL_RESORT&sort=RECOMMENDED&openPlayBack=true) ![](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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Resort-Hotels.d184066-aaResortHotels.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Resort-Hotels.d184066-aaResortHotels.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![My Place Hotel-Randolph VT](//images.trvl-media.com/lodging/106000000/105670000/105665800/105665795/a55aa0fa_y.jpg) ### My Place Hotel-Randolph VT 10/10 Excellent "Elevator not working " [](https://expedia.ca/My-Place-Hotel-Randolph-VT.h105665795.Hotel-Information) ![Cozy Loft for two with Hot Tub & Mtn Views](//images.trvl-media.com/lodging/60000000/59790000/59784500/59784421/434c8b92_y.jpg) ### Cozy Loft for two with Hot Tub & Mtn Views 10/10 Excellent "The cozy loft was just as advertised. Nice little isolated cabin. We enjoyed our stay. " [](https://expedia.ca/Granville-Hotels-Romantic-Loft-With-Hot-Tub.h59784421.Hotel-Information) ![Brandon Inn](//images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/ec2b6d3b_y.jpg) ### Brandon Inn 10/10 Excellent "The service was excellent. They were very pet friendly. Our dog (mix golden retriever & Afghan hound) was overjoyed with her attention." [](https://expedia.ca/Brandon-Hotels-Brandon-Inn.h25184647.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) ![Mountain Sports Inn](//images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/7b3b252e_y.jpg) ### Mountain Sports Inn 10/10 Excellent "Clean room, friendly staff " [](https://expedia.ca/Killington-Hotels-Mountain-Sports-Inn.h1339833.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) ## Find out more about Pittsfield ## Pittsfield Resorts information | Number of reviews | 628 | | --- | --- | | Accommodation | 3 Resorts | | Lowest Price | CA $450 | | Highest Price | CA $692 | ## Frequently asked questions ### What is Pittsfield like for a resort vacation? > You deserve to get away, and a resort is the ideal place to pamper yourself with the services and amenities you need for a relaxing stay in Pittsfield. One of the comfortable resort hotels in the surrounding area could be just what you're searching for, whether you want great restaurants on site, blissful spa treatments, or fun activities to try. ### What's a top resort for my stay in Pittsfield? > Here are our top-rated resorts near Pittsfield: [Woodstock Inn & Resort](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) - Luxury resort. 17.9 mi (28.9 km) from Pittsfield. Features 4 restaurants, 2 bars, and a golf course. [The Mountain Top Inn & Resort](https://www.expedia.ca/Chittenden-Hotels-The-Mountain-Top-Inn-Resort.h9673261.Hotel-Information) - Beach resort. 6.9 mi (11.1 km) from Pittsfield. Has a private beach, ski-in/ski-out access, and a seasonal outdoor pool. [On The Mountain - 1 - Bedroom - Sleeps 6](https://www.expedia.ca/Killington-Hotels-On-The-Mountain-1-Bedroom-Sleeps-6.h102321389.Hotel-Information) - Located right by Killington Resort. 10.1 mi (16.3 km) from Pittsfield. Enjoy the fitness center. ### What can I do in Pittsfield? > Green Mountain National Forest, Roger Clark Memorial Central Library, and Pittsfield Town Hall are a few of the interesting sights to visit. Other attractions in the area include Green Mountain National Golf Course and Gifford Woods State Park. ### What's the seasonal weather like in Pittsfield? > 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. ### What's the best way to get to and around Pittsfield? > Fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is located 18.1 mi (29.2 km) away from the heart of the city. 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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