Title: The Best Pittsfield, VT Resorts from $283 | 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 Next weekend [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-05-15&endDate=2026-05-17&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pittsfield resorts ![The Jewel | Living area | TV](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/53dd6cd4.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 Jewel | Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/369f7f98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Brookside Upper | Living area | TV](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/1e72639e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mountain Top Inn & Resort [](https://www.expedia.com/Chittenden-Hotels-The-Mountain-Top-Inn-Resort.h9673261.Hotel-Information) Chittenden 9.0/10 Wonderful (111 reviews) "Great resort " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Adam $260 nightly $283 total Mar 23 - Mar 24 Total with taxes and fees [](https://www.expedia.com/Chittenden-Hotels-The-Mountain-Top-Inn-Resort.h9673261.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/fd07b171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/645e5fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/1c6e2228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodstock Inn & Resort [](https://www.expedia.com/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) Woodstock 9.2/10 Wonderful (569 reviews) "Amazing restaurant and attentive staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Noelle $349 nightly $384 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/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.com/Hotel-Search?startDate=2026-04-03&endDate=2026-04-04®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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Resorts.d184066-aaResorts.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Resorts.d184066-aaResorts.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![Summit Lodge](https://images.trvl-media.com/lodging/2000000/1110000/1102600/1102506/bdef58fa_y.jpg) ### Summit Lodge 10/10 Excellent "Great stay " [](https://expedia.com/Killington-Hotels-Summit-Lodge.h1102506.Hotel-Information) ![North Star Lodge and Resort](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/17fcad53_y.jpg) ### North Star Lodge and Resort 10/10 Excellent "Really friendly and helpful staff. Excellent bar and grille, pool and exercise room with generous hours. A little noisy as some parents let their kids free range about. However, very comfortable room, beds and great views." [](https://expedia.com/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.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 "The staff were exceptional. " [](https://expedia.com/Rutland-Hotels-Best-Western-Inn-Suites-Rutland-Killington.h16411.Hotel-Information) ![Killington Mountain Lodge, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/f9bd2dd9_y.jpg) ### Killington Mountain Lodge, Tapestry Collection by Hilton 8/10 Good "Yes" [](https://expedia.com/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![Days Inn by Wyndham Rutland/Killington Area](https://images.trvl-media.com/lodging/1000000/890000/889600/889570/4a1f2dfa_y.jpg) ### Days Inn by Wyndham Rutland/Killington Area 10/10 Excellent "always kind people " [](https://expedia.com/Rutland-Hotels-Days-Inn-By-Wyndham-RutlandKillington-Area.h889570.Hotel-Information) ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/8d6bfa64_y.jpg) ### On The River Inn 10/10 Excellent "Just a great property all around. For going a few minutes down the road from downtown you get a very well appointed, updated hotel. Breakfast was excellent, pool and Sauna are is nicely updated. Amazingly kid friendly, will be back soon! " [](https://expedia.com/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![The Mountain Top Inn & Resort](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/53dd6cd4_y.jpg) ### The Mountain Top Inn & Resort 10/10 Excellent "Staff all friendly and helpful. Loved the free electric car charging ports in parking area." [](https://expedia.com/Chittenden-Hotels-The-Mountain-Top-Inn-Resort.h9673261.Hotel-Information) ![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/fd07b171_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "Excellent!!" [](https://expedia.com/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![Comfort Inn Rutland - Killington](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/b2987a71_y.jpg) ### Comfort Inn Rutland - Killington 10/10 Excellent "Great!" [](https://expedia.com/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Resorts information | Number of reviews | 680 | | ----------------- | --------- | | Accommodation | 3 Resorts | | Lowest Price | $283 | | Highest Price | $384 | ## Frequently asked questions ### What is Pittsfield like for a resort vacation? ### What's a top resort for my stay in Pittsfield? ### What can I do in Pittsfield? ### What's the seasonal weather like in Pittsfield? ### What's the best way to get to and around Pittsfield? ## 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) - 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