Title: Pittsfield Condo Rentals from CA $316 | 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://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Condos Rentals in Pittsfield from CA $316 - ![](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 [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Pittsfield Condo Rentals ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/109000000/108490000/108481700/108481634/65aa0189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108490000/108481700/108481634/2c84fe84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108490000/108481700/108481634/63742f7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108490000/108481700/108481634/8a3fd2ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool. Killington 10/10 Exceptional (2) "The place was perfect for our trip, close to the lifts and the bike park. Host kept good communication throughout the trip from beginning to the end. Would definitely recommend if you are headed to Killington for the bike park." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott D. CA $172 CA $583 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Killington-Hotels-Trail-Creek-Killington-Condos-18-Ski-Home-Trail-Bus-Hot-Tub-Pool.h108481634.Hotel-Information) ![Condo, 1 Bedroom, Kitchen, Garden View | Terrace/patio](https://images.trvl-media.com/lodging/122000000/121200000/121193900/121193871/668c2f83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 1 Bedroom, Garden View | Private kitchen](https://images.trvl-media.com/lodging/122000000/121200000/121193900/121193871/9c65fc7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/122000000/121200000/121193900/121193871/0ce108b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 1 Bedroom, Kitchen, Garden View | Private kitchen](https://images.trvl-media.com/lodging/122000000/121200000/121193900/121193871/04a5f2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Suites at Killington Center Killington CA $154 CA $477 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Killington-Hotels-The-Suites-At-Killington-Center.h121193871.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113560000/113559600/113559586/89b58050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 3 Bedrooms | Pool](https://images.trvl-media.com/lodging/114000000/113560000/113559600/113559586/033d8c56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/114000000/113560000/113559600/113559586/b28868af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113560000/113559600/113559586/9a9d7936.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Killington Ski Resort VT Vacation Condos Killington CA $167 CA $413 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Killington-Hotels-Killington-Ski-Resort-VT-Vacation-Condos.h113559586.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108900000/108898500/108898462/e224bbd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/109000000/108900000/108898500/108898462/2122b1d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108900000/108898500/108898462/d3006cd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108900000/108898500/108898462/fc29842d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 3-Bedroom Whiffletree Condo in Killington, VT with Ski-In/Shuttle Access. Ski rental deals. Killington 9.0/10 Wonderful (2) "Beautiful condo. Convenient proximity to slopes. Neighbors upstairs were load til 3am partying but not the fault of the owner." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JR M. CA $151 CA $556 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Killington-Hotels-Cozy-3-Bedroom-Whiffletree-Condo-In-Killington.h108898462.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73360000/73359800/73359716/b200a527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/74000000/73360000/73359800/73359716/79c1859e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73360000/73359800/73359716/aea17d8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73360000/73359800/73359716/418364b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A Killington 9.2/10 Wonderful (5) "I don’t think I’ve ever had such wonderful service checking in and caring for our needs. Amazing response time and outstanding stay. Thank you." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret L. CA $109 CA $328 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Killington-Hotels-Fall-Line-Studio-Condo-With-Mountain-Views-On-Shuttle-Route-B4A.h73359716.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77980000/77972800/77972752/1aec1bb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/78000000/77980000/77972800/77972752/a9d39a60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/78000000/77980000/77972800/77972752/82db2c3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/78000000/77980000/77972800/77972752/34ab1387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CozyCub- Location, Fireplace, Ski Off/Shuttle On! Killington 10/10 Exceptional (22) "Great place to stay and close to the mountain!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sam S. CA $114 CA $391 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Killington-Hotels-CozyCub-Cheerful-Haven-Nestled-On-The-Mountain.h77972752.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/73000000/72400000/72393800/72393787/fa6543fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/73000000/72400000/72393800/72393787/b7093446.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/73000000/72400000/72393800/72393787/2f15c511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/73000000/72400000/72393800/72393787/159c2547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities G2A Killington 8.8/10 Excellent (3) "Great location, just the right size, and comfy beds." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike H. CA $100 CA $316 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Killington-Hotels-Fall-Line-Studio-Condo-With-Mountain-Views-On-Shuttle-Route-G2A.h72393787.Hotel-Information) ![Fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/41000000/40070000/40061100/40061003/fe9fc9a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/41000000/40070000/40061100/40061003/f8c8d73c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/41000000/40070000/40061100/40061003/f25b9b58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/41000000/40070000/40061100/40061003/d834834a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service Killington 9.4/10 Exceptional (63) "Comfortable condo in convenient location near Ramshead. Access to the newly renovated health spa: indoor pool, sauna and hot tub a real bonus. Great place for a few days skiing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $125 CA $341 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Killington-Hotels-Snowshed-Ramshead-Ski-Lodges-In-Walking-Distance-Plus-Shuttle-Service.h40061003.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/73000000/72480000/72476800/72476795/ac97c810.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72480000/72476800/72476795/7fa3ee11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/73000000/72480000/72476800/72476795/f3aa5dae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72480000/72476800/72476795/b90869be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Snow Better Place: Perfect for Two - On Shuttle Route w/ Amenities Killington 7.4/10 Good (3) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason D. CA $117 CA $339 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Killington-Hotels-Beautiful-Fall-Line-Condo-With-Mountain-Views-On-Shuttle-Route-E2A.h72476795.Hotel-Information) ![TV, DVD player, books](https://images.trvl-media.com/lodging/91000000/90150000/90149600/90149596/0431a8e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/90150000/90149600/90149596/8663ca25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books](https://images.trvl-media.com/lodging/91000000/90150000/90149600/90149596/6b3e0077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90150000/90149600/90149596/e29469ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5th-floor mountain-view condo, easy access to the slopes free shuttle or walk Killington 9.4/10 Exceptional (9) "Could use some updates and the cleaning staff needs to be more thorough." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah S. CA $112 CA $371 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Killington-Hotels-5th-Floor-Mountain-View-Condo.h90149596.Hotel-Information) ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/110000000/109320000/109311900/109311827/dd2c68b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/110000000/109320000/109311900/109311827/6d55b1a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109320000/109311900/109311827/b78a0dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/110000000/109320000/109311900/109311827/8a2dee32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access The Woods 10/10 Exceptional (3) "We headed up to Killington for some fun spring skiing with the fam and the place was great - spacious, well appointed, and comfortable. Would definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan T. CA $196 CA $634 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Killington-Hotels-Woods-Resort-And-Spa-Cozy-2-Bedroom-Condo-In-Killington.h109311827.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38820000/38813900/38813831/9db9bf68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/39000000/38820000/38813900/38813831/54b024ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38820000/38813900/38813831/4f6fe36f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38820000/38813900/38813831/b2147bc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Killington Blue Studio: Sleeps 4, Close to Mtn 123 Killington 9.4/10 Exceptional (9) "Great location and clean property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) KEVIN C. CA $96 CA $318 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Central-Vermont-Killington-Hotels-Killington-Blue-Studio-Sleeps-4.h38813831.Hotel-Information) ![Condo, 2 Bedrooms | Dining](https://images.trvl-media.com/lodging/91000000/90020000/90019400/90019372/f9cbb469.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms | Pool](https://images.trvl-media.com/lodging/91000000/90020000/90019400/90019372/1a544915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms | Property grounds](https://images.trvl-media.com/lodging/91000000/90020000/90019400/90019372/c5ad1ca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/91000000/90020000/90019400/90019372/c9692d73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Woods by Killington Vacation Rentals - 2 Bedrooms The Woods 10/10 Exceptional (2) "The condo had everything we needed for a comfortable and enjoyable stay. The pool and hot tub area were great additions. We would definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $266 CA $873 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Killington-Hotels-The-Woods-By-Killington-Vacation-Rentals-2-Bedrooms.h90019372.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/111000000/110290000/110285500/110285457/8a3c8472.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110290000/110285500/110285457/0d2fff39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110290000/110285500/110285457/ffa20544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110290000/110285500/110285457/d058a909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington Killington 9.6/10 Exceptional (4) "The place was clean and easy to get to. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah Z. CA $106 CA $341 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Killington-Hotels-Tranquil-Peaks-Studio-At-Killington-Center-Perfect-For-A-Getaway-In-The-Heart-Of-Killington.h110285457.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60280000/60276000/60275959/45800a08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/61000000/60280000/60276000/60275959/694ff574.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/61000000/60280000/60276000/60275959/w1980h1318x0y0-28191568.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/61000000/60280000/60276000/60275959/w828h546x0y3-bf2a1b77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ⛷ 1BR Ski-Home Condo. Pool/Hot Tub/Sauna. Short walk 2 lifts, golf, hikes. Killington 10/10 Exceptional (21) "Excellent location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Colin G. CA $188 CA $424 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Killington-Hotels-1BR-Ski-Home-Condo-PoolHot-TubSauna-Short-Walk-2-Lifts.h60275959.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/111000000/110670000/110666200/110666145/50fcf717_edited_1faf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110670000/110666200/110666145/a951dbfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110670000/110666200/110666145/207a4566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/111000000/110670000/110666200/110666145/50b8e88f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Alpine Oasis Studio at Mountain Green Resort Killington: Shuttle, Pool, Hot Tub, Gym, Deals! Killington 9.6/10 Exceptional (5) "The location was perfect. The unit had everything in it that we needed. We will definitely come back again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) AMY W. CA $128 CA $409 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Killington-Hotels-Alpine-Oasis-Studio-At-Mountain-Green-Resort-Killington-Shuttle.h110666145.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/70000000/69330000/69323900/69323855/3be45e67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/70000000/69330000/69323900/69323855/c69a44ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/70000000/69330000/69323900/69323855/2384b10c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69330000/69323900/69323855/7d0bfe7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunrise West Glade: 3BR, 3BA Ski In/Ski Out Condo Killington 9.4/10 Exceptional (16) "Perfect ski in ski out location. Unit is as represented. Issue on check in when we arrived it was uncleaned and we spent first hour of occupancy with the cleaning crew. Also was ongoing leak in master bedroom from roof which saturated the carpet. This was obviously of long standing duration and rather disgusting. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jon d. CA $237 CA $813 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Killington-Hotels-Sunrise-West-Glade-3BR.h69323855.Hotel-Information) ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/73000000/72700000/72690500/72690470/215fa4aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/73000000/72700000/72690500/72690470/9183cd2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/73000000/72700000/72690500/72690470/e33d85bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/73000000/72700000/72690500/72690470/872a9c4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### FirBear- Pool, Gym, Hot tub. The Woods 10/10 Exceptional (22) "Everything was exactly as pictured and the hosts of the property went above and beyond with their hospitality " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $162 CA $570 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Killington-Hotels-FirBear-New-And-Renovated-2-BR-2-Bath-Condo.h72690470.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109330000/109324300/109324214/20f29130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/110000000/109330000/109324300/109324214/e8535060.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/110000000/109330000/109324300/109324214/8919996b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109330000/109324300/109324214/da44e8d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2 BR Ski On Ski Off Condo in Killington's Sunrise Mountain Village. Pool. Hot Tub. Killington 9.4/10 Exceptional (3) "Absolutely perfect spot. Kids and parents loved it. Everything you’re looking for in an on mountain condo. Pool and hot tub are a short drive away but we still used it. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) nicholas d. CA $271 CA $754 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Killington-Hotels-Cozy-2-BR-Ski-On-Ski-Off-Condo-In-Killingtons-Sunrise-Mountain-Village-Discounted-Lift-Tickets.h109324214.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83790000/83784200/83784152/f34478b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/84000000/83790000/83784200/83784152/59ffb652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83790000/83784200/83784152/40e5679a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83790000/83784200/83784152/10370e6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### YOUR KILLINGTON BASECAMP 3A4: Free shuttle w/Pool & Hot tub Killington 9.8/10 Exceptional (25) "Stunning location for hiking and biking. Beautiful fall colors on the mountain for our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joanne M. CA $243 CA $583 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Killington-Hotels-Killington-Mnt-2Br2Ba-SkiGolfBikeHikePool.h83784152.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=2025-11-27&endDate=2025-11-28®ionId=184066&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-02-11&d1=2026-02-11&endDate=2026-02-14&d2=2026-02-14&lodging=VACATION_HOME) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-02-11&d1=2026-02-11&endDate=2026-02-14&d2=2026-02-14&lodging=APARTMENT) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-02-11&d1=2026-02-11&endDate=2026-02-14&d2=2026-02-14&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-02-11&d1=2026-02-11&endDate=2026-02-14&d2=2026-02-14&lodging=COTTAGE) Condos [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-02-11&d1=2026-02-11&endDate=2026-02-14&d2=2026-02-14&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-02-11&d1=2026-02-11&endDate=2026-02-14&d2=2026-02-14&lodging=VILLA) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-02-11&d1=2026-02-11&endDate=2026-02-14&d2=2026-02-14&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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Condos.d184066-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Condos.d184066-aaCondos.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![Hampton Inn Rutland](//images.trvl-media.com/lodging/2000000/1530000/1523000/1522922/f4f05fc2_y.jpg) ### Hampton Inn Rutland 10/10 Excellent "Loved the whole hotel staff was great and very helpful and it was very clean!!!" [](https://expedia.ca/Rutland-Hotels-Hampton-Inn-Rutland.h1522922.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 "Jeff is very friendly and answered all my questions in a very reasonable amount of time the cabin was very cozy very clean very relaxing would definitely recommend it to friends it was an incredibly relaxing experience." [](https://expedia.ca/Granville-Hotels-Romantic-Loft-With-Hot-Tub.h59784421.Hotel-Information) ![The Shire Woodstock](//images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Large, clean room with nice view. Unique. " [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![Brandon Inn](//images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/ec2b6d3b_y.jpg) ### Brandon Inn 10/10 Excellent "The Brandon Inn is one of my favorite places to stay. The location is great, with 2 outstanding taverns/pubs, a breakfast/lunch diner brewery and a fine dining resturant all within a 2 minute walk. The Inn itself is outstanding. With the historic ambiance, antique furniture and artifacts through out the halls and rooms, and the renovation and preservation of what the Inn was like 200 years ago, it is truly a trip back through time. May the Brandon Inn have success for many years to come. " [](https://expedia.ca/Brandon-Hotels-Brandon-Inn.h25184647.Hotel-Information) ![On The River Inn](//images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/528a7f5b_y.jpg) ### On The River Inn 10/10 Excellent "Staff were fantastic " [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Days Inn by Wyndham Rutland/Killington Area](//images.trvl-media.com/lodging/1000000/890000/889600/889570/2b102593_y.jpg) ### Days Inn by Wyndham Rutland/Killington Area 10/10 Excellent "Staff was very polite and curious " [](https://expedia.ca/Rutland-Hotels-Days-Inn-By-Wyndham-RutlandKillington-Area.h889570.Hotel-Information) ![The Jackson ](//images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg) ### The Jackson 10/10 Excellent "Loved the casual, comfortable, easy atmosphere. Homey and welcoming but never overbearing. Staff were all wonderful and personable. " [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.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 "Everything was great except for the mattress was shot it caved in the center ,yes I would return ." [](https://expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.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 "Room was spotless and comfortable. Dog friendly, hassle free stay. Cleanliness was top tier, and staff was fantastic!" [](https://expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Condo Rentals information | Number of reviews | 199 | | --- | --- | | Accommodation | 587 Condo Rentals | | Lowest Price | CA $316 | | Highest Price | CA $873 | ## Frequently asked questions ### How much do condos in Pittsfield cost? > The price range for condos in Pittsfield is CA $316 to CA $873 per night. No matter your budget, you'll find someplace that suits your needs — as well as your entire squad! These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### What are the best condos in Pittsfield? > Pittsfield offers multiple condos with a total average guest review rating of 9.6. [Silver Spring Chalet - Getaway](https://www.expedia.ca/Pittsfield-Hotels-Silver-Spring-Chalet-GetAway.h33305034.Hotel-Information) is one highly recommended option. Guests staying at this 3-star condo will enjoy amenities such as a furnished patio and a fireplace. [Slopeside Pico 3 Bedroom Condo](https://www.expedia.ca/Slopeside-Pico-3-Bedroom-Condo.h19657810.Hotel-Information) is another popular choice. This 3-star property offers a swimming pool and ski-in/ski-out facilities. ### How many condos are there in Pittsfield? > You can choose from 587 condos in Pittsfield. No matter if you're traveling with the kids or organizing a weekend break with some friends, Expedia can help you find the perfect space for your entire crew. ### Are there any family-friendly condos in Pittsfield? > Put your feet up at [Silver Spring Chalet - Getaway](https://www.expedia.ca/Pittsfield-Hotels-Silver-Spring-Chalet-GetAway.h33305034.Hotel-Information), a 3-star option not far from town. Conveniences here include a furnished patio and a fireplace. Another family-friendly condo is [Slopeside Pico 3 Bedroom Condo](https://www.expedia.ca/Slopeside-Pico-3-Bedroom-Condo.h19657810.Hotel-Information). Ski-in/ski-out facilities and a swimming pool help make this 3-star escape a hit with guests. Once you've checked in and unpacked your suitcase, there are loads of family-friendly attractions to explore in and around Pittsfield. [Pico Mountain at Killington Ski Resort](https://www.expedia.ca/Pico-Mountain-At-Killington-Ski-Resort-Killington.d6082891.Vacation-Attraction) and [Gifford Woods State Park](https://www.expedia.ca/Gifford-Woods-State-Park-Killington.d6291277.Vacation-Attraction) guarantee fun for all ages. ### Why book your condo in Pittsfield with Expedia? > With Expedia, it's easy to find your dream condo in Pittsfield. After a luxury stay? Take advantage of our filters to search for properties that are 5-star rated. If you have a budget in mind, click on how much you'd like to spend and then check out our amazing deals. We'll help you find a suitable stay whatever your style of travel or plans. ### How can I find cheap condos in Pittsfield? > Expedia can help you narrow your search for cheap condos in Pittsfield. 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[Vacation Homes in Stockbridge](https://www.expedia.ca/Stockbridge-Private-Vacation-Homes.d6357893-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Flights to Killington](https://www.expedia.ca/Cheap-Flights-To-Killington.d10780.Travel-Guide-Flights) - [Fire Tower](https://www.expedia.ca/Fire-Tower-Killington.d553248621532667609.Vacation-Attraction) - [Gifford Woods State Park](https://www.expedia.ca/Gifford-Woods-State-Park-Killington.d6291277.Vacation-Attraction) - [Green Mountain National Golf Course](https://www.expedia.ca/Green-Mountain-National-Golf-Course-Killington.d6115884.Vacation-Attraction) - [Killington School for Tennis](https://www.expedia.ca/Killington-School-For-Tennis-Killington.d553248621532667625.Vacation-Attraction) - [Killington Vacations](https://www.expedia.ca/Killington.d10780.Destination-Travel-Guides) - [Visit Killington](https://www.expedia.ca/Killington.dx10780) - [Pico Mountain at Killington Ski Resort](https://www.expedia.ca/Pico-Mountain-At-Killington-Ski-Resort-Killington.d6082891.Vacation-Attraction) - 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