Title: Pittsfield Holiday Homes from £74: Search Holiday Homes in Pittsfield | Expedia.co.uk [Pittsfield Travel Guide](https://expedia.co.uk/Pittsfield.dx184066)[Hotels in Pittsfield](https://expedia.co.uk/Pittsfield-Hotels.d184066.Travel-Guide-Hotels)[Holiday Rentals in Pittsfield](https://expedia.co.uk/Pittsfield-Holiday-Rentals.d184066.Travel-Guide-HolidayRentals)[Pittsfield Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Pittsfield.d184066.Car-Hire-Guide)[Pittsfield Holidays](https://expedia.co.uk/Pittsfield.d184066.Holidays-City-Breaks) ![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__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 In two weeks [17 Apr - 19 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=184066&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [29 May - 31 May](https://www.expedia.co.uk/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) In three months [26 Jun - 28 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=184066&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [24 Jul - 26 Jul](https://www.expedia.co.uk/Hotel-Search?regionId=184066&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pittsfield holiday homes ![Smart TV, offices](https://images.trvl-media.com/lodging/124000000/123490000/123480200/123480177/e1256054.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/124000000/123490000/123480200/123480177/22b8d20a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123490000/123480200/123480177/586cbc8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123490000/123480200/123480177/00bd424c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking [](https://www.expedia.co.uk/Pittsfield-Hotels-NEW-Smart-3BR-Basecamp-W-Hot-Tub.h123480177.Hotel-Information) North Sherburne £451 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Pittsfield-Hotels-NEW-Smart-3BR-Basecamp-W-Hot-Tub.h123480177.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109080000/109073500/109073427/3e594ac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Toilet paper](https://images.trvl-media.com/lodging/110000000/109080000/109073500/109073427/f6f584ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109080000/109073500/109073427/8ab70085.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/110000000/109080000/109073500/109073427/c8e537d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Off Grid Glamping Shed with River Access [](https://www.expedia.co.uk/Off-Grid-Glamping-Shed-With-River-Access.h109073427.Hotel-Information) Randolph 10/10 Exceptional (1 review) £74 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Off-Grid-Glamping-Shed-With-River-Access.h109073427.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/101000000/100340000/100335500/100335420/5630d307.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100340000/100335500/100335420/22048f13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100340000/100335500/100335420/1b6e3563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100340000/100335500/100335420/9d0ca37f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### new 2 bedroom close to killington and bike trails this is pet ok downstairs unit [](https://www.expedia.co.uk/Rutland-Hotels-New-2-Bedroom-Close-To-Killington-And-Bike-Trailsthis-Is-Pet-Ok-Downstairs-Unit.h100335420.Hotel-Information) Mendon 9.8/10 Exceptional (6 reviews) "Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aurore H. £172 includes taxes & fees 12 Apr - 13 Apr [](https://www.expedia.co.uk/Rutland-Hotels-New-2-Bedroom-Close-To-Killington-And-Bike-Trailsthis-Is-Pet-Ok-Downstairs-Unit.h100335420.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/128000000/127430000/127428300/127428264/30adea26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/128000000/127430000/127428300/127428264/2369d7cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/128000000/127430000/127428300/127428264/5e2bec88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/128000000/127430000/127428300/127428264/7e0bff2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2-Bedroom Unit in Plymouth, Vt. Central to Killington, Woodstock & Okemo! [](https://www.expedia.co.uk/Plymouth-Hotels-2-Bedroom-Unit-In-Plymouth.h127428264.Hotel-Information) Plymouth £75 includes taxes & fees 28 Apr - 29 Apr [](https://www.expedia.co.uk/Plymouth-Hotels-2-Bedroom-Unit-In-Plymouth.h127428264.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120660000/120652400/120652390/19bccfea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120660000/120652400/120652390/1083183d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Games room](https://images.trvl-media.com/lodging/121000000/120660000/120652400/120652390/e502214a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120660000/120652400/120652390/8634aa3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace [](https://www.expedia.co.uk/Killington-Hotels-Cozy-2BR-Mountain-Retreat-Near-Killington-Resort-Pet-Friendly-W-Fireplace.h120652390.Hotel-Information) Killington £317 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Killington-Hotels-Cozy-2BR-Mountain-Retreat-Near-Killington-Resort-Pet-Friendly-W-Fireplace.h120652390.Hotel-Information) ![TV, stereo](https://images.trvl-media.com/lodging/108000000/107780000/107773500/107773414/b288df60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107780000/107773500/107773414/c07b75b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107780000/107773500/107773414/fdc22138.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, stereo](https://images.trvl-media.com/lodging/108000000/107780000/107773500/107773414/99cb431b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Killington Retreat | Deck-Fire Pit-Mountain Views! [](https://www.expedia.co.uk/North-Clarendon-Hotels-OPEN-Custom-Vacation-Retreat-In-Killington-Valley.h107773414.Hotel-Information) Clarendon 9.0/10 Wonderful (4 reviews) "Beautiful house! It had everything we needed for a fun and relaxing week. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joshua £290 includes taxes & fees 4 Apr - 5 Apr [](https://www.expedia.co.uk/North-Clarendon-Hotels-OPEN-Custom-Vacation-Retreat-In-Killington-Valley.h107773414.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/adb899cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/f1b12770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/c9400bbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/b023884e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CozyDen-Location, Ski Off/Shuttle On! [](https://www.expedia.co.uk/Killington-Hotels-CozyDen-AC.h100501897.Hotel-Information) Killington 9.0/10 Wonderful (2 reviews) "Place was clean and location was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Berni H. £214 includes taxes & fees 5 Apr - 6 Apr [](https://www.expedia.co.uk/Killington-Hotels-CozyDen-AC.h100501897.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/75000000/74280000/74276300/74276210/24beae4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74280000/74276300/74276210/8f122202.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, stereo](https://images.trvl-media.com/lodging/75000000/74280000/74276300/74276210/d1a5de2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/75000000/74280000/74276300/74276210/88f078e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Big Lebearski! Hot Tub, FirePlace! [](https://www.expedia.co.uk/Killington-Hotels-The-Big-Lebearski-Cheerful-4BR-In-Killington.h74276210.Hotel-Information) Killington 10/10 Exceptional (19 reviews) "Great location and excellent hosts " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter G. £527 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Killington-Hotels-The-Big-Lebearski-Cheerful-4BR-In-Killington.h74276210.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/c3df7e46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, table football, offices](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/1b212a1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/9f5da7f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/f1219ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large Killington Area Home | Sleeps 7 | Game Room [](https://www.expedia.co.uk/Bridgewater-Hotels-Bridgewater-Inn-2-King-Beds-Game-Room-Skiing.h90692944.Hotel-Information) Bridgewater 9.6/10 Exceptional (7 reviews) "My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Owen C. £410 includes taxes & fees 14 Apr - 15 Apr [](https://www.expedia.co.uk/Bridgewater-Hotels-Bridgewater-Inn-2-King-Beds-Game-Room-Skiing.h90692944.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/123000000/122590000/122582200/122582186/87e5dd2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122590000/122582200/122582186/08ac2d76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122590000/122582200/122582186/6d334060.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122590000/122582200/122582186/9ba7459a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vermont Retreat: 3BR with Mountain Views and Trails [](https://www.expedia.co.uk/Brookfield-Hotels-Vermont-Retreat-3BR-With-Mountain-Views-And-Trails.h122582186.Hotel-Information) Brookfield £452 includes taxes & fees 1 Apr - 2 Apr [](https://www.expedia.co.uk/Brookfield-Hotels-Vermont-Retreat-3BR-With-Mountain-Views-And-Trails.h122582186.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/111000000/110220000/110215300/110215244/ef58d29c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110220000/110215300/110215244/a10e4151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/111000000/110220000/110215300/110215244/ffc555c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/111000000/110220000/110215300/110215244/f7208238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes. [](https://www.expedia.co.uk/Bridgewater-Corners-Hotels-Cozy-Vermont-House-Near-Killington-And-Woodstock-Discounted-Lift-Tickets.h110215244.Hotel-Information) Bridgewater 8.0/10 Very good (2 reviews) "Great place for a ski weekend" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathryn F. £512 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Bridgewater-Corners-Hotels-Cozy-Vermont-House-Near-Killington-And-Woodstock-Discounted-Lift-Tickets.h110215244.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108620000/108611900/108611818/39d074f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108620000/108611900/108611818/c21943f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/109000000/108620000/108611900/108611818/1716f4e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/109000000/108620000/108611900/108611818/949bc3f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Feel the real VT! Ski Killington and a foodie’s delight! [](https://www.expedia.co.uk/Proctor-Hotels-Feel-The-Real-VT-Lakes.h108611818.Hotel-Information) Proctor 10/10 Exceptional (1 review) "Clean and comfortable home. Plenty of space for our family! Great quiet neighborhood made it easy to relax on our trip." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca £400 includes taxes & fees 13 Apr - 14 Apr [](https://www.expedia.co.uk/Proctor-Hotels-Feel-The-Real-VT-Lakes.h108611818.Hotel-Information) ![TV, offices](https://images.trvl-media.com/lodging/103000000/102050000/102041800/102041769/eeabbdeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102050000/102041800/102041769/11f6cb0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102050000/102041800/102041769/87269be8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102050000/102041800/102041769/1f37c646.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Tower House | Hot Tub | Firepit | Dog-Friendly [](https://www.expedia.co.uk/Killington-Hotels-Hot-Tub-Sauna-The-Tower-House.h102041769.Hotel-Information) Killington 9.0/10 Wonderful (2 reviews) "Great place, near everything and great customer service!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick B. £503 includes taxes & fees 20 Apr - 21 Apr [](https://www.expedia.co.uk/Killington-Hotels-Hot-Tub-Sauna-The-Tower-House.h102041769.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105780000/105777700/105777639/6f79e5c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/106000000/105780000/105777700/105777639/583d8f0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105780000/105777700/105777639/edbb7161.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105780000/105777700/105777639/ebda3bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub. [](https://www.expedia.co.uk/Killington-Hotels-Fun-In-Fun-Out-Ski-Home-Main-Floor-Renovated-3BR2BA-Hot-Tub-Lift-Tickets.h105777639.Hotel-Information) Killington 10/10 Exceptional (1 review) "Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine S. £457 includes taxes & fees 6 Apr - 7 Apr [](https://www.expedia.co.uk/Killington-Hotels-Fun-In-Fun-Out-Ski-Home-Main-Floor-Renovated-3BR2BA-Hot-Tub-Lift-Tickets.h105777639.Hotel-Information) ![Smart TV, fireplace, table football, offices](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663187/7a76e14a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table football, offices](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663187/72c46fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663187/f01d8207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663187/26b11e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4BR Killington Home Perfect for Families, Pet-Friendly [](https://www.expedia.co.uk/Killington-Hotels-4BR-Killington-Home-Perfect-For-Families.h120663187.Hotel-Information) North Sherburne 10/10 Exceptional (23 reviews) "Spacious, clean and cozy home. Perfect for a ski trip or weekend getaway." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darko G. £549 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Killington-Hotels-4BR-Killington-Home-Perfect-For-Families.h120663187.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304254/31553740.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304254/49ae6ebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304254/eede2581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304254/f03ca5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown [](https://www.expedia.co.uk/Rutland-Hotels-Spacious-Central-4BR.h119304254.Hotel-Information) Rutland 10/10 Exceptional (4 reviews) "House was clean, organized and spacious. Great location as well, close to grocery, gas and restaurants. Host answered questions quickly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dominic C. £321 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Rutland-Hotels-Spacious-Central-4BR.h119304254.Hotel-Information) ![House, 6 Bedrooms | Living area](https://images.trvl-media.com/lodging/91000000/90030000/90027900/90027835/1f9e32bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 3 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/91000000/90030000/90027900/90027835/8921270b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 6 Bedrooms | Living area](https://images.trvl-media.com/lodging/91000000/90030000/90027900/90027835/8c4c5576.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 3 Bedrooms | Dining](https://images.trvl-media.com/lodging/91000000/90030000/90027900/90027835/91328bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Breakaway House by Killington Vacation Rentals [](https://www.expedia.co.uk/Killington-Hotels-Breakaway-House-By-Killington-Vacation-Rentals.h90027835.Hotel-Information) Killington £579 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Killington-Hotels-Breakaway-House-By-Killington-Vacation-Rentals.h90027835.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/36000000/35370000/35361300/35361208/b635093d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35370000/35361300/35361208/f2b8cc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35370000/35361300/35361208/921092b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35370000/35361300/35361208/d7bc9b42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Classic Vermont Farmhouse near Sugarbush Resort [](https://www.expedia.co.uk/Warren-Hotels-Classic-Vermont-Farmhouse-Near-Sugarbush-Resort.h35361208.Hotel-Information) Warren 9.6/10 Exceptional (50 reviews) "Charming older home, clearly well loved. Enjoyed eating on the back porch, the generous living room space, and the sinks in every bedroom!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathalie B. [](https://www.expedia.co.uk/Warren-Hotels-Classic-Vermont-Farmhouse-Near-Sugarbush-Resort.h35361208.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/72000000/71670000/71662400/71662324/91b2debc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/72000000/71670000/71662400/71662324/9be9adf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/72000000/71670000/71662400/71662324/0ae1aa65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/72000000/71670000/71662400/71662324/8a7b5a3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Royalbear - Hot Tub, Fireplace, Close to Slopes [](https://www.expedia.co.uk/Killington-Hotels-RoyalBear-Lux-Chalet-Retreat-2-Miles-To-Slope.h71662324.Hotel-Information) Killington 10/10 Exceptional (23 reviews) "Great house and location, and responsive hosts. Loved it, def will stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Max P. £684 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Killington-Hotels-RoyalBear-Lux-Chalet-Retreat-2-Miles-To-Slope.h71662324.Hotel-Information) ![Smart TV, fireplace, ping pong](https://images.trvl-media.com/lodging/124000000/123010000/123005000/123004903/3b3f3195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123010000/123005000/123004903/34d4ec8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/124000000/123010000/123005000/123004903/b95a841c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, ping pong](https://images.trvl-media.com/lodging/124000000/123010000/123005000/123004903/256e5a32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bear Paw Cabin: 3 Living Areas, Hot Tub & Chef's Kitchen 5 Mins to Pico [](https://www.expedia.co.uk/Rutland-Hotels-Bear-Paw-Cabin-3-Living-Areas.h123004903.Hotel-Information) Mendon 10/10 Exceptional (2 reviews) "Great house, location, and easy check in / out" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John G. £578 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Rutland-Hotels-Bear-Paw-Cabin-3-Living-Areas.h123004903.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.co.uk/Hotel-Search?startDate=2026-04-13&endDate=2026-04-14®ionId=184066&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=APARTMENT) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=VACATION_HOME) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=CONDO) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=COTTAGE) Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=CABIN) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=VILLA) Chalets [](https://www.expedia.co.uk/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Private-Holiday-Homes.d184066-aaPrivateHolidayHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Private-Holiday-Homes.d184066-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![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 4/10 Poor "they save a lot" [](https://expedia.co.uk/Rutland-Hotels-Days-Inn-By-Wyndham-RutlandKillington-Area.h889570.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 "Convenient location but it is not ski in ski out as described in listing. " [](https://expedia.co.uk/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![Summit Lodge](https://images.trvl-media.com/lodging/2000000/1110000/1102600/1102506/bdef58fa_y.jpg) ### Summit Lodge 10/10 Excellent "Clean \*enough\* room. Linens and bath robe had slight stains but nothing overly worrying. Room was clean, no smell. Floor creaked like crazy due to old wood flooring. Second time staying up here this year. Love the ambience and the location. Unfortunately, we came just as O'Dwyer's and the hotel were about to shut down for the season. The check-in counter does have a very limited selection of beer and wine, but it's just not quite the right atmosphere when you finish skiing/snowboarding, pop into the hot tub but buy a beer from the lobby first. If O'Dwyer's was open OR if we had known they were shutting down when we booked, it would have let us prepare a little better." [](https://expedia.co.uk/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 "We just stayed one night at this hotel. The room was just outdated but pretty clean. We did notice on the morning there were two beers from the night before. They also have an outdoor heated pool that we didn't get to check out because it was raining but you can see Killington from the pool on clearer days." [](https://expedia.co.uk/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![My Place Hotel-Randolph VT](https://images.trvl-media.com/lodging/106000000/105670000/105665800/105665795/430b34b8_y.jpg) ### My Place Hotel-Randolph VT 10/10 Excellent "Excellent. " [](https://expedia.co.uk/My-Place-Hotel-Randolph-VT.h105665795.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 10/10 Excellent "Great location and shuttle service. Nice breakfast and friendly staff. " [](https://expedia.co.uk/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![Mountain Sports Inn](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/fae277d0_y.jpg) ### Mountain Sports Inn 10/10 Excellent "Nice quiet Clean rooms and plenty of parking. " [](https://expedia.co.uk/Killington-Hotels-Mountain-Sports-Inn.h1339833.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 "Clean room, comfortable bed Great steakhouse next door" [](https://expedia.co.uk/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.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 " Very cozy. Lovely breakfast. Fun smores" [](https://expedia.co.uk/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Holiday Homes information | Number of reviews | 121 | | ----------------- | ----------------- | | Accommodation | 559 Holiday Homes | | Lowest Price | £74 | | Highest Price | £684 | ## Explore a world of travel with Expedia - More ways to book - [Book Holiday Homes in Pittsfield on Expedia.com ](https://www.expedia.com/Pittsfield-Private-Vacation-Homes.d184066-aaPrivateVacationHomes.Travel-Guide-Accommodation)