Title: Pittsfield Vacation Home Rentals from CA $722: Search Top Private Vacation Homes for Rent | 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) # Pittsfield Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Pittsfield Vacation Homes ![Property grounds](https://images.trvl-media.com/lodging/115000000/114400000/114397800/114397721/cb3fb1ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114400000/114397800/114397721/60409579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114400000/114397800/114397721/66a92d4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114400000/114397800/114397721/c63de027.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glamping hut with WiFi in Ripton, biking, hiking, skiing Ripton CA $124 CA $233 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Ripton-Hotels-Glamping-Hut-With-WiFi-In-Ripton.h114397721.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109480000/109476300/109476281/a9515c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/110000000/109480000/109476300/109476281/5e456de4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109480000/109476300/109476281/w1175h800x25y0-e4bf9cad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/110000000/109480000/109476300/109476281/db902092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont North Sherburne CA $223 CA $737 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Pittsfield-Hotels-Peak-Hill-3-Bedroom.h109476281.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109080000/109073500/109073427/8ab70085.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109080000/109073500/109073427/3e594ac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109080000/109073500/109073427/e3fee229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109080000/109073500/109073427/cdf61965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Off Grid Glamping Shed with River Access Randolph 10/10 Exceptional (1) CA $82 CA $130 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Off-Grid-Glamping-Shed-With-River-Access.h109073427.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097860/ea91e459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097860/2fbac199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097860/a40db391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097860/906f227a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Condo Tucked in the Heart of Killington Killington CA $141 CA $424 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Killington-Hotels-Luxury-Condo-Tucked-In-The-Heart-Of-Killington.h119097860.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/b8d48b25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108620000/108611900/108611818/5d61da3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108620000/108611900/108611818/6320bd7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Feel the real VT! Fall foliage, hikes, foodie’s delight! Proctor 10/10 Exceptional (1) "Clean and comfortable home. Plenty of space for our family! Great quiet neighborhood made it easy to relax on our trip." CA $208 CA $738 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Proctor-Hotels-Feel-The-Real-VT-Lakes.h108611818.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/121000000/120810000/120807700/120807632/42acc43a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/121000000/120810000/120807700/120807632/203b44f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120810000/120807700/120807632/cac92949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120810000/120807700/120807632/2af364e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cabin, Mountain Views, Hot Tub, Pool, Basketball Court, Fire Pit in Rutland Rutland CA $209 CA $269 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Rutland-Hotels-Cozy-Cabin.h120807632.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105780000/105777700/105777639/dcbc9b92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105780000/105777700/105777639/47ba2040.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/ec60e8e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/106000000/105780000/105777700/105777639/42b859a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub. Killington 10/10 Exceptional (1) "Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. " CA $238 CA $765 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Killington-Hotels-Fun-In-Fun-Out-Ski-Home-Main-Floor-Renovated-3BR2BA-Hot-Tub-Lift-Tickets.h105777639.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/acc10e06.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) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/743b417c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CozyDen - AC, Grill, Bike to Mountain, Porch! Killington 10/10 Exceptional (1) "Very quiet and private feeling even though it is in a condo like setting. Very clean, and had all the conveniences we needed (A/C, coffee maker, full kitchen appliances). And so kind and personal to leave some souvenirs of the area. We felt very comfortable when every we finished our day of sightseeing to come back to our home away from home. " CA $131 CA $404 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Killington-Hotels-CozyDen-AC.h100501897.Hotel-Information) ![Smart TV, fireplace, foosball, offices](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663187/7a76e14a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663187/5b1c0638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663187/d8e327f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663187/9a68181d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4BR Killington Home Perfect for Families, Pet-Friendly North Sherburne 10/10 Exceptional (22) "This was our second time staying at the house. Fantastic house for a long weekend skiing at Killington. Plenty of room for the adults and teens to unwind after a day on the slopes! Will definitely visit again. " CA $282 CA $973 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Killington-Hotels-4BR-Killington-Home-Perfect-For-Families.h120663187.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/121000000/120660000/120652400/120652390/4a76f043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120660000/120652400/120652390/3018839a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120660000/120652400/120652390/35d88107.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/121000000/120660000/120652400/120652390/28fc792a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace Killington CA $230 CA $574 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Killington-Hotels-Cozy-2BR-Mountain-Retreat-Near-Killington-Resort-Pet-Friendly-W-Fireplace.h120652390.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68050000/68047700/68047644/b5f630ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/69000000/68050000/68047700/68047644/c64a751b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68050000/68047700/68047644/94f2014d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68050000/68047700/68047644/65f3071f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful home located in the Mad River Valley Warren 9.8/10 Exceptional (38) "We had a great time staying at this house during our Sugarbush skiing trip this February. The place is easy to access and is close to the ski resort. The house had everything we needed for a comfortable stay. I highly recommend this rental." [](https://www.expedia.ca/Warren-Hotels-Beautiful-Home-Located-In-The-Mad-River-Valley.h68047644.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108300000/108296500/108296432/4909dc2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108300000/108296500/108296432/2764b0a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108300000/108296500/108296432/c90a724b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108300000/108296500/108296432/f5817cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bomoseen Bungalow: Vermont Lake House with Private Dock Bomoseen 10/10 Exceptional (2) "Nice place to stay. Very well equipped and clean." CA $293 CA $842 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Bomoseen-Hotels-The-Bomoseen-Bungalow.h108296432.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/112000000/111420000/111411200/111411190/5e2fb8ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/112000000/111420000/111411200/111411190/0326abbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111420000/111411200/111411190/5200e83b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111420000/111411200/111411190/90789a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful oasis, stunning views, less than 10 mins from Woodstock Village Pomfret 10/10 Exceptional (1) "Beautiful, spacious, clean, relaxing home and property. Loved it! Would stay here again." CA $426 CA $806 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/South-Pomfret-Hotels-Peaceful-Oasis.h111411190.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/111000000/110270000/110263700/110263621/4a9f4ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110270000/110263700/110263621/26d30fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110270000/110263700/110263621/ede4f789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110270000/110263700/110263621/31a757f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Top of the Hill Modern Retreat East Warren 9.6/10 Exceptional (5) "Really nice place everything was top notch. " CA $217 CA $821 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Warren-Hotels-Top-Of-The-Hill-Modern-Retreat.h110263621.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22480000/22479200/22479176/1340ba74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/23000000/22480000/22479200/22479176/b5820dd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/23000000/22480000/22479200/22479176/7adb4eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22480000/22479200/22479176/32b5bf72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush granville 9.2/10 Wonderful (80) "Cool old farm house with an old fashioned set-up. Good value for the money considering how many people the house sleeps. Bathrooms are updated, kitchen is from the 80s. Furniture is outdated and ready to be replaced. Beds were very soft, not supportive. " CA $124 CA $425 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Hancock-Hotels-52-Old-Farmhome-Beautiful-Valley-Views-Near-Skiing-Sugarbush.h22479176.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/112000000/111240000/111231500/111231408/eec0ec39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111240000/111231500/111231408/ce2ab39c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111240000/111231500/111231408/48729af6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/112000000/111240000/111231500/111231408/b364bc2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington Killington 9.2/10 Wonderful (5) "Our group was in town for an archery event nearby and the location was perfect. Its peaceful and quiet but close to everything. It is an older house but well taken care of. Would definitely recommend. " CA $273 CA $758 total includes taxes & fees Oct 10 - Oct 11 [](https://www.expedia.ca/Killington-Hotels-The-SHACK-3BR15BA-Home-W-Hot-Tub-And-Discounted-Lift-Ticket-Deals.h111231408.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104790000/104789700/104789606/1c960e95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/105000000/104790000/104789700/104789606/b4350eb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104790000/104789700/104789606/6d068748.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104790000/104789700/104789606/be338c0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Powder Park Place: Lower Unit. Cozy and close to the Mountain! Discounted ski rentals. Killington 10/10 Exceptional (2) "A very comfortable stay for a family of four. Close to everything, clean, well stocked for breakfast making, and just enough room for everyone. We really enjoyed the fireplace after a day of skiing.Not sure why the heat setting turned to low 60s every night, but our blankets were warm." CA $169 CA $580 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Killington-Hotels-Powder-Park-Place-Lower-Unit-Cozy-And-Close-To-The-Mountain-Discounted-Lift-Tickets.h104789606.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/56000000/55190000/55184800/55184767/eec7f68a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/56000000/55190000/55184800/55184767/aa49b005.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, streaming services, music library, video library](https://images.trvl-media.com/lodging/56000000/55190000/55184800/55184767/fd2ba366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, streaming services, music library, video library](https://images.trvl-media.com/lodging/56000000/55190000/55184800/55184767/8ea18e84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Breakaway House: Renovated Killington Duplex, Unit A. Close to Resort. Killington 7.6/10 Good (4) "Great location, clean and quiet." CA $204 CA $637 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Killington-Hotels-Breakaway-House-Renovated-Killington-Duplex.h55184767.Hotel-Information) ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/101000000/100830000/100822600/100822513/3523e734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100830000/100822600/100822513/6c93e544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/101000000/100830000/100822600/100822513/df0eafeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100830000/100822600/100822513/0bf9adcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna The Woods 10/10 Exceptional (6) "Great location and a great place. Felt right at home" CA $185 CA $695 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Killington-Hotels-Bearmont-Pool.h100822513.Hotel-Information) ![Golf](https://images.trvl-media.com/lodging/102000000/101250000/101243900/101243826/c575999d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101250000/101243900/101243826/82d94d09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/102000000/101250000/101243900/101243826/45e652e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101250000/101243900/101243826/404aed07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Grizz- AC, Pool, Sauna, Gym, Near Resort Killington 10/10 Exceptional (4) "Place was overall great and just as advertised. Beds were awesome including the Murphy bed. Thanks for a wonderful weekend! I would definitely stay again. " CA $148 CA $605 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Killington-Hotels-TheGrizz-Bike-And-Ski-Shuttle-On-Off-By-Golf.h101243826.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=2025-10-20&endDate=2025-10-21®ionId=184066&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Private-Vacation-Homes.d184066-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Private-Vacation-Homes.d184066-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![Greenbrier Inn](//images.trvl-media.com/lodging/2000000/1180000/1176800/1176792/e5569f51_y.jpg) ### Greenbrier Inn 10/10 Excellent "Love it. Thank you so much. Slept like a baby" [](https://expedia.ca/Killington-Hotels-Greenbrier-Inn.h1176792.Hotel-Information) ![Mountain Sports Inn](//images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/7b3b252e_y.jpg) ### Mountain Sports Inn 10/10 Excellent "Great " [](https://expedia.ca/Killington-Hotels-Mountain-Sports-Inn.h1339833.Hotel-Information) ![Best Western Inn & Suites Rutland-Killington](//images.trvl-media.com/lodging/1000000/20000/16500/16411/9898f616_y.jpg) ### Best Western Inn & Suites Rutland-Killington 10/10 Excellent "Our room was great! We got an upgrade and our room even had a patio! " [](https://expedia.ca/Rutland-Hotels-Best-Western-Inn-Suites-Rutland-Killington.h16411.Hotel-Information) ![Comfort Inn Rutland - Killington](//images.trvl-media.com/lodging/1000000/10000/4700/4621/15d4fef0_y.jpg) ### Comfort Inn Rutland - Killington 10/10 Excellent "Great place to stay. Well kept." [](https://expedia.ca/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.Hotel-Information) ![Cortina Inn](//images.trvl-media.com/lodging/1000000/30000/27000/27000/aa6e8386_y.jpg) ### Cortina Inn 6/10 Okay "This hotel appears to be in the middle of a renovation (9/26/25). Room was clean and comfortable. Hallways and outside need work. Very few amenities." [](https://expedia.ca/Rutland-Hotels-Cortina-Inn.h27000.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 "Best place in Killington!" [](https://expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.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 "Central location in Vermont! Best place I stay at up on Killington. Has fireplace with sitting area in lobby, game room, coffee in morning and a Heated Pool! The grounds are. Ice with picnic tables around pond! Located near everything in mountain!" [](https://expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![Brandon Inn](//images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/ec2b6d3b_y.jpg) ### Brandon Inn 10/10 Excellent "Historic building very well maintained. Friendly and helpful staff. Great location in town " [](https://expedia.ca/Brandon-Hotels-Brandon-Inn.h25184647.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 "The staff was fantastic the room was clean and they allowed me to bring my dog " [](https://expedia.ca/Rutland-Hotels-Days-Inn-By-Wyndham-RutlandKillington-Area.h889570.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Vacation Homes information | Number of reviews | | | --- | --- | | Accommodation | 664 Vacation Homes | | Lowest Price | CA $722 | | Highest Price | CA $1,577 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Killington](https://www.expedia.ca/4Star-Killington-Hotels.s40-0-d10780.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Chittenden](https://www.expedia.ca/Chittenden-Hotels-Cheap-Hotels.0-0-d184042-tCheapHotels.Travel-Guide-Filter-Hotels) - 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