Title: Pittsfield Cottages from CA $152 | 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 Pittsfield Cottage Rentals from CA $152 - ![](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 [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 weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Pittsfield Cottages No exact matches found, but these alternatives could be just right ## Recommended hotels in Pittsfield ![Exterior](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522922/f4f05fc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![32-inch LCD TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522922/14edbde8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522922/7aefc770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522922/075005f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Rutland 9.0/10 Wonderful (966) "Very clean, good location, and super helpful staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sheryl CA $189 CA $208 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Rutland-Hotels-Hampton-Inn-Rutland.h1522922.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/15d4fef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/62720c61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/325364db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/6cdf9844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Rutland - Killington 8.0/10 Very good (1013) "Clean, great steak house by the hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caridad CA $163 CA $179 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/106000000/105670000/105665800/105665795/663c443a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/106000000/105670000/105665800/105665795/430b34b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, desk, blackout drapes](https://images.trvl-media.com/lodging/106000000/105670000/105665800/105665795/94482c61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/106000000/105670000/105665800/105665795/82cb2ed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### My Place Hotel-Randolph VT 9.4/10 Exceptional (339) "Awesome staff and great room with Kitchenette" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $140 CA $153 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/My-Place-Hotel-Randolph-VT.h105665795.Hotel-Information) ![House, 4 Bedrooms | Exterior](https://images.trvl-media.com/lodging/108000000/107560000/107550500/107550402/3b0a27aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 4 Bedrooms | Outdoor spa tub](https://images.trvl-media.com/lodging/108000000/107560000/107550500/107550402/504f7a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 4 Bedrooms | Dining](https://images.trvl-media.com/lodging/108000000/107560000/107550500/107550402/c881e78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 4 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/108000000/107560000/107550500/107550402/979ffbf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Pittsfield CA $605 CA $1,366 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Pittsfield-Hotels-The-Getaway-4-Bedroom-Home.h107550402.Hotel-Information) ![Deluxe Suite | Exterior](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/896352ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/7b3a7c11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Accessible, Dog-Friendly Double](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/53cc1cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/32c31fca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel in Woodstock 9.6/10 Exceptional (546) "Clean, friendly, easy check in, welcoming accommodations. Can’t wait to come back" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $108 CA $229 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/c3cb22fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/302c3d84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/a73c2787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/05237c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Shire Woodstock 8.8/10 Excellent (886) "Upon entering the hotel, the lobby is gorgeous with 2 fireplaces. Staff was super friendly and the free breakfast was a bonus. The room was spotless and has a fireplace in the room. My wife and I loved this place and will definitely go back. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vincent CA $161 CA $188 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/8d6bfa64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/c49d548b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/cd26b573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### On The River Inn 9.4/10 Exceptional (1009) "This place was charming!! Enjoyed everything about it and so much to do right there in the inn." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ross CA $332 CA $416 total includes taxes & fees Dec 5 - Dec 6 [](https://www.expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/6aabd3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/5f513e0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/e0958349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bed & Breakfast in West Woodstock 9.8/10 Exceptional (256) "Very cute inn, the restaurant was a plus. Had a great dinner there and def will come back. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaunita [](https://www.expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/17fcad53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/0612ebf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/db156eb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/bed9fca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Star Lodge and Resort 8.6/10 Excellent (1000) "Spotless room also very accommodating and friendly! Loved our short stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Candace CA $147 CA $162 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/33fd758e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Double Room, Garden View](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/abaf26b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/d7baa23b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Double Room, Courtyard View](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/01f9a10a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bed & Breakfast in Woodstock 10/10 Exceptional (46) "Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $278 CA $306 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Woodstock-Hotels-Stay-At-Jimmys.h103188664.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/f9bd2dd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/0dbf9fa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Billiards](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/b1730c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/2b1767e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Killington Mountain Lodge, Tapestry Collection by Hilton 7.4/10 Good (1000) "It’s a small beautiful cabin like/feel hotel and they have everything you need and most esp a quick drive to Killington resort Their food is also very good and well prepared. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $205 CA $226 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/894100/894095/7d78fd71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/900000/894100/894095/dc32203b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served](https://images.trvl-media.com/lodging/1000000/900000/894100/894095/f9d7db28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Farmhouse Thundering Brook | Living area](https://images.trvl-media.com/lodging/1000000/900000/894100/894095/537271c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Meadows Lodge 9.4/10 Exceptional (178) "All round fantastic place to stay " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Stephen CA $229 CA $287 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Killington-Hotels-Mountain-Meadows-Lodge.h894095.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/7b3b252e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/783dc891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/75edb3bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, free cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/34a1ed27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Sports Inn 8.8/10 Excellent (977) "This is a great place to stay. Attentive staff, easy parking, lots of options on the continental breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lana CA $139 CA $152 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Killington-Hotels-Mountain-Sports-Inn.h1339833.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/114000000/113900000/113896300/113896234/044ad9b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/114000000/113900000/113896300/113896234/w1333h750x0y0-a24444d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Double Room, River View](https://images.trvl-media.com/lodging/114000000/113900000/113896300/113896234/148d42ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113900000/113896300/113896234/5d2c48fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn in West Woodstock 8.6/10 Excellent (57) "A very pleasant VT stay at a reasonable price." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean CA $176 CA $194 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Woodstock-Hotels-Lincoln-Inn-Gallery.h113896234.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/19000000/18550000/18540700/18540657/ccb90de5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18550000/18540700/18540657/4273b3c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/19000000/18550000/18540700/18540657/71a3bcfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/19000000/18550000/18540700/18540657/e79916d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lodge in Killington 8.8/10 Excellent (270) "We enjoyed our stay. Close proximity to a lot of things to see and do. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda CA $177 CA $194 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Killington-Hotels-Turn-Of-River-Lodge.h18540657.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/9000000/8280000/8270200/8270194/aa03edab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/9000000/8280000/8270200/8270194/34a3d8c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Queen Room with View](https://images.trvl-media.com/lodging/9000000/8280000/8270200/8270194/dc02869f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Queen Room with Spring](https://images.trvl-media.com/lodging/9000000/8280000/8270200/8270194/23d8da75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bed & Breakfast in Killington 9.6/10 Exceptional (189) "Absolutely lovely stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $154 CA $174 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Killington-Hotels-Mountain-Valley-Retreat.h8270194.Hotel-Information) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/374f8e02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/72849c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/3cca622a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mountain Inn at Killington 9.2/10 Wonderful (952) "Great place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen CA $248 CA $286 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/5000000/4610000/4603200/4603194/33e9ebe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served](https://images.trvl-media.com/lodging/5000000/4610000/4603200/4603194/2603f226.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room 30 | Room amenity](https://images.trvl-media.com/lodging/5000000/4610000/4603200/4603194/28388992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room 22](https://images.trvl-media.com/lodging/5000000/4610000/4603200/4603194/7e388eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn in South Woodstock 9.0/10 Wonderful (326) "Nice place to stay. Would stay there again & recommend it to friends and family " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah CA $307 CA $338 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/South-Woodstock-Hotels-Kedron-Valley-Inn.h4603194.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/30000/27000/27000/f9974bae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/30000/27000/27000/aa6e8386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27000/27000/e84e42c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/27000/27000/f085d98b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cortina Inn 6.6/10 (646) "Hostess was very kind " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jayme CA $138 CA $152 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Rutland-Hotels-Cortina-Inn.h27000.Hotel-Information) ![Economy Room](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/ae1d5a64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/199515ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/62f98cd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/589572bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bed & Breakfast in Woodstock 9.2/10 Wonderful (46) "Cute B&B, great location! Easy walk to coffee house and downtown area. We really enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roger CA $239 CA $263 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Woodstock-Hotels-The-Vesper.h103415437.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=2025-12-17&endDate=2025-12-18®ionId=184066&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_184066) ## Find vacation rentals that suit your style 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=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=CABIN) 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=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=APARTMENT) 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=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&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=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=CONDO) 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=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=VACATION_HOME) 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=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&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=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&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-Cottages.d184066-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Cottages.d184066-aaCottages.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![Killington Mountain Lodge, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/403a8548_y.jpg) ### Killington Mountain Lodge, Tapestry Collection by Hilton 10/10 Excellent "If you want to travel to Killington with your pup, this is a great spot to stay! Right next to a golf course and other open space for dogs to run. Super friendly staff (Tahoe got lots of treats from the front desk). Great location. Good breakfast. Nice outdoor hot tub for a soak after hitting the nearby slopes." [](https://expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![North Star Lodge and Resort](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/0612ebf1_y.jpg) ### North Star Lodge and Resort 10/10 Excellent "Spotless room also very accommodating and friendly! Loved our short stay!" [](https://expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![The Jackson ](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg) ### The Jackson 10/10 Excellent "Fabulous " [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Courtyard Middlebury](https://images.trvl-media.com/lodging/1000000/970000/970000/969917/587431c4_y.jpg) ### Courtyard Middlebury 10/10 Excellent "Very clean room staff very helpful" [](https://expedia.ca/Middlebury-Hotels-Courtyard-Middlebury.h969917.Hotel-Information) ![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "Top notch service. Great property and beautiful room. Went for anniversary and it did not disappoint. Romantic hotel and town" [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![Mountain Meadows Lodge](https://images.trvl-media.com/lodging/1000000/900000/894100/894095/7995d81d_y.jpg) ### Mountain Meadows Lodge 10/10 Excellent "Amenities were very nice. " [](https://expedia.ca/Killington-Hotels-Mountain-Meadows-Lodge.h894095.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 "The front desk staff are patient and enthusiastic." [](https://expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![Days Inn by Wyndham Rutland/Killington Area](https://images.trvl-media.com/lodging/1000000/890000/889600/889570/2b102593_y.jpg) ### Days Inn by Wyndham Rutland/Killington Area 10/10 Excellent "Clean room" [](https://expedia.ca/Rutland-Hotels-Days-Inn-By-Wyndham-RutlandKillington-Area.h889570.Hotel-Information) ![Brandon Inn](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/ec2b6d3b_y.jpg) ### Brandon Inn 10/10 Excellent "Accommodated mobility limitations and friendly very courteous staff!" [](https://expedia.ca/Brandon-Hotels-Brandon-Inn.h25184647.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Cottages information | Number of reviews | 10,674 | | --- | --- | | Accommodation | 39 Cottages | | Lowest Price | CA $152 | | Highest Price | CA $1,366 | ## Frequently asked questions ### Why book your cottage in Pittsfield with Expedia? > We think that a vacation should be a breeze, so if you're chasing cottages in Pittsfield at an affordable price, Expedia is here to help. Keep the budget in check and stay in an economical option surrounded by nature, or splurge on a luxury cottage to treat your loved ones. ### How can I find cheap cottages in Pittsfield? > With Expedia's filter tool, comparing cheap cottages in Pittsfield has never been easier. 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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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