Title: Pittsfield, VT Cottage Rentals from $179 | 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 [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 31 - Aug 2](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-07-31&endDate=2026-08-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pittsfield cottages ![Exterior](https://images.trvl-media.com/lodging/83000000/82970000/82961200/82961114/e1c21b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/83000000/82970000/82961200/82961114/27f50440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82970000/82961200/82961114/0c83964c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/83000000/82970000/82961200/82961114/452ffb91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pristine Custom Cottage, Grand Piano, Massage Studio on Site [](https://www.expedia.com/Brandon-Hotels-Luxurious-Secluded-Cottage-Massage-Studio-On-Site.h82961114.Hotel-Information) Leicester 10/10 Exceptional (73 reviews) "Great place to stay for a Vermont getaway! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeremy H. $160 nightly $179 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Brandon-Hotels-Luxurious-Secluded-Cottage-Massage-Studio-On-Site.h82961114.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107910000/107909000/107908933/1730b6e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107910000/107909000/107908933/49463cd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107910000/107909000/107908933/0c26463f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/108000000/107910000/107909000/107908933/d79ef6b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland. [](https://www.expedia.com/Rutland-Hotels-The-Mendon-Cottage-Charming-Home-Close-To-Killington-Discounted-Lift-Tickets.h107908933.Hotel-Information) Mendon 9.8/10 Exceptional (14 reviews) "Great place! Secluded but close to everything. We will definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia Y. $361 nightly $404 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Rutland-Hotels-The-Mendon-Cottage-Charming-Home-Close-To-Killington-Discounted-Lift-Tickets.h107908933.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=2026-04-20&endDate=2026-04-21®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=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=CABIN) 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=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=COTTAGE) 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=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=VACATION_HOME) 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=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=APARTMENT) 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=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=CONDO) 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=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=VILLA) 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=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=CHALET) ![](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-Cottages.d184066-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Cottages.d184066-aaCottages.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/8d6bfa64_y.jpg) ### On The River Inn 8/10 Good "Everything was cool except the rude woman bartending at the 506 bistro" [](https://expedia.com/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Hampton Inn Rutland](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522922/5a9cd2d5_y.jpg) ### Hampton Inn Rutland 10/10 Excellent "We had a great stay, very clean and the staff was friendly! " [](https://expedia.com/Rutland-Hotels-Hampton-Inn-Rutland.h1522922.Hotel-Information) ![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/fd07b171_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "Always an Amazing time when we stay here. Property well maintained, staff is super friendly and the food here is above and beyond. Did I mention I got married here đź‘Ťđź‘Ť" [](https://expedia.com/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![Mountain Sports Inn](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/fae277d0_y.jpg) ### Mountain Sports Inn 10/10 Excellent "Yes" [](https://expedia.com/Killington-Hotels-Mountain-Sports-Inn.h1339833.Hotel-Information) ![The Mountain Inn at Killington](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441_y.jpg) ### The Mountain Inn at Killington 8/10 Good "Nice place close to the mountain with an attentive and friendly staff. Very clean and well run. It’s not a resort or a place where you stay to enjoy the hotel. You are here to ski / board and this is your place to return to for drinks and a good night sleep. The AC wasn’t working well when we were there but it was still late Winter so not unexpected (was unseasonably warm). The furniture in the sitting areas upstairs needs to be upgraded since that’s really the only place to hangout in morning or afternoons other than the restaurant. Overall very pleased with the place for the price." [](https://expedia.com/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![Turn of River Lodge](https://images.trvl-media.com/lodging/19000000/18550000/18540700/18540657/4273b3c6_y.jpg) ### Turn of River Lodge 10/10 Excellent "Super cute little place to stay" [](https://expedia.com/Killington-Hotels-Turn-Of-River-Lodge.h18540657.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 "Bathrooms need an update" [](https://expedia.com/Rutland-Hotels-Best-Western-Inn-Suites-Rutland-Killington.h16411.Hotel-Information) ![Brandon Inn](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/194828e3_y.jpg) ### Brandon Inn 10/10 Excellent "Wonderful spot right on the town square. " [](https://expedia.com/Brandon-Hotels-Brandon-Inn.h25184647.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 "Bar is a great touch!" [](https://expedia.com/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Cottages information | Number of reviews | 87 | | ----------------- | ----------- | | Accommodation | 42 Cottages | | Lowest Price | $179 | | Highest Price | $404 | ## Frequently asked questions ### Why book your cottage in Pittsfield with Expedia? ### How can I find cheap cottages in 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) - [Stockbridge Hotels ](https://www.expedia.com/Stockbridge-Hotels.d6357893.Travel-Guide-Hotels) - 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