Title: Ashuwillticook Rail Trail Vacation Home Rentals from CA $340: Search Top Private Vacation Homes for Rent | Expedia.ca [Ashuwillticook Rail Trail Travel Guide](https://expedia.ca/Ashuwillticook-Rail-Trail.dx811531152953708544)[Hotels in Ashuwillticook Rail Trail](https://expedia.ca/Ashuwillticook-Rail-Trail-Hotels.d811531152953708544.Travel-Guide-Hotels)[Vacation Rentals in Ashuwillticook Rail Trail](https://expedia.ca/Ashuwillticook-Rail-Trail-Vacation-Rentals.d811531152953708544.Travel-Guide-VacationRentals)[Flights to Ashuwillticook Rail Trail](https://expedia.ca/Cheap-Flights-To-Ashuwillticook-Rail-Trail.d811531152953708544.Travel-Guide-Flights)[Ashuwillticook Rail Trail Car Rentals](https://expedia.ca/Car-Rentals-In-Ashuwillticook-Rail-Trail.d811531152953708544.Car-Rental-Guide)[Ashuwillticook Rail Trail Vacation Packages](https://expedia.ca/Ashuwillticook-Rail-Trail.d811531152953708544.Destination-Travel-Guides) ![Made a little friend while walking the rail trail!](https://images.trvl-media.com/place/6005408/30b30c82-45cb-4d89-b1b6-fabb3b302b19.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Chris Addams # Ashuwillticook Rail Trail Vacation Rentals - ![](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 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=811531152953708544&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) In two weeks [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=811531152953708544&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 one month [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=811531152953708544&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=811531152953708544&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Ashuwillticook Rail Trail Vacation Homes ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/ecdea449.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/116000000/115470000/115470000/115469906/162d61f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/4bbc4f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/51a25809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Sherwood Forest 10/10 Exceptional (4) "We loved it! Lots of local hiking trails and a wonderful relaxing place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon K. CA $205 CA $529 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/af01e53f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/dba15cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/c04d3199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/347359ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Sherwood Forest 9.6/10 Exceptional (10) "Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James D. CA $225 CA $537 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/5dc2bebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/14ecae77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/12b81391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/f0c8191e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Florida 10/10 Exceptional (4) "Place was super clean. Beds were comfortable. Location was great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tristan e. CA $258 CA $475 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/North-Adams-Hotels-Florida-Mountain-Log-Cabin.h90251080.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/aac07fd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/493cc38e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/775a6169.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/c178e2db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Bennington 8.6/10 Excellent (34) "Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ransom W. CA $140 CA $381 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Bennington-Hotels-Two-Brooks-Lodge.h61478133.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/6ba9f20d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/7ec1e2c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/04d66d5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/516bcaba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Whitingham 10/10 Exceptional (14) "Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacklyn D. CA $307 CA $738 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Whitingham-Hotels-14mi-To-Mt-Snow-Arcade.h100720354.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/fbef3554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/65181381.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/1df26d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/f0ba5959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lebanon Springs 8.8/10 Excellent (20) "It was great - just what we were looking for. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kaye S. CA $182 CA $511 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w907h683x58y0-59aad182.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w510h683x258y0-04b5e846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w507h683x259y0-1d5f8c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, printers](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w919h683x60y0-f3238385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Williamstown 9.2/10 Wonderful (24) "The cottage was the perfect accommodations for our overnight stay in town for a funeral. Thank you Claudia. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary Alice H. CA $284 CA $632 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Getaway-Or-Remote-Workschool-Location.h60763766.Hotel-Information) ![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/406cc767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/c57b8d60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, eco-friendly cleaning products](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/780d89c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Great Barrington 9.4/10 Exceptional (6) CA $284 CA $418 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/6339dfc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/333900eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/a7e5baab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/3bd0d6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Housatonic 10/10 Exceptional (3) "Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl F. CA $189 CA $340 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.Hotel-Information) ![Panoramic House | Private kitchen](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/6511d75d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic House](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/106aa7f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/3358f5ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic House | Private kitchen](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/f721b80c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Bennington 4.8/10 (3) "Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hunter [](https://www.expedia.ca/Bennington-Hotels-Two-Brooks-Lodge.h83780792.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/8a26cf53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/976ef973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/11a36f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/d4f0c0c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Hancock 9.8/10 Exceptional (72) "Great communication. Lots of games for the kids. Comfortable beds. Great living and game room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samuel R. CA $370 CA $768 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Hancock-Hotels-Spacious-3BR-3BA-Ski-OnOff-Jiminy-Mountain-Resort.h67635438.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/5858308d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/6616eba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/c910a979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/fa499ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Florida 10/10 Exceptional (4) "Wonderful view, peaceful quiet area, cosy cabin." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $368 CA $613 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/North-Adams-Hotels-True-Cabin-In-The-Woods-New-Log-Cabin-With-View-Of-Mt-Greylock.h119137863.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/f305b62e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/037efde9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/d80b29aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/597105fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Charlemont CA $224 CA $580 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Charlemont-Hotels-Riverbend-Berkshire-East-Basecamp-3-Bedrooms-Available.h120461825.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/a38bbe4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/3fc8dc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/adca2c72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/44aa4835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Pittsfield 7.8/10 Good (6) "Very clean and spacious! We enjoyed our stay with our small pup!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann C. CA $377 CA $693 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/18066543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/dcf5df54_edited_d00b.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/110000000/109440000/109435000/109434975/6658a41d_edited_267e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/f076ba69_edited_5004.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Hancock 9.0/10 Wonderful (7) "Kind and responsive host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Javier CA $452 CA $1,027 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Hancock-Hotels-Comfortable-Berkshires-Retreat-On-Mtn-Resort.h109434975.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/98889bac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/42550a03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/d94e7ffd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/a49402a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Old Chatham CA $268 CA $662 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Old-Chatham-Hotels-Artists-Hideaway-In-Old-Chatham.h121082559.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/c038a4f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/4f43280b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/b87b098e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/1163baa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Charlemont CA $516 CA $929 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Charlemont-Hotels-Charlemont-Chalet-Where-The-Mountains-Meet-Luxury.h121902882.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/58b0972d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/d06b32cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/8b34823f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/fb68a83f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lee 8.0/10 Very good (1) "House was large, clean, and comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John Z. CA $536 CA $1,043 total includes taxes & fees Dec 5 - Dec 6 [](https://www.expedia.ca/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/5d0aa061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/34fa691f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/c8837e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/w1440h1084x0y1-9f76bc91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Hancock 10/10 Exceptional (15) "Amazing Inn. Cozy and everything we needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Price F. CA $771 CA $1,471 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Pittsfield-Hotels-Hancock-Village-Inn-At-Jiminy-Peak.h89806253.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=2025-12-12&endDate=2025-12-13®ionId=811531152953708544&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_811531152953708544) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Ashuwillticook+Rail+Trail%2C+Massachusetts%2C+United+States+of+America®ionId=811531152953708544&latLong=42.55483%2C-73.16379&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Ashuwillticook+Rail+Trail%2C+Massachusetts%2C+United+States+of+America®ionId=811531152953708544&latLong=42.55483%2C-73.16379&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=APARTMENT) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Ashuwillticook+Rail+Trail%2C+Massachusetts%2C+United+States+of+America®ionId=811531152953708544&latLong=42.55483%2C-73.16379&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Ashuwillticook+Rail+Trail%2C+Massachusetts%2C+United+States+of+America®ionId=811531152953708544&latLong=42.55483%2C-73.16379&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=COTTAGE) Condos [](https://www.expedia.ca/Hotel-Search?destination=Ashuwillticook+Rail+Trail%2C+Massachusetts%2C+United+States+of+America®ionId=811531152953708544&latLong=42.55483%2C-73.16379&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=CONDO) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Ashuwillticook+Rail+Trail%2C+Massachusetts%2C+United+States+of+America®ionId=811531152953708544&latLong=42.55483%2C-73.16379&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=VACATION_HOME) Villas [](https://www.expedia.ca/Hotel-Search?destination=Ashuwillticook+Rail+Trail%2C+Massachusetts%2C+United+States+of+America®ionId=811531152953708544&latLong=42.55483%2C-73.16379&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=VILLA) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Ashuwillticook+Rail+Trail%2C+Massachusetts%2C+United+States+of+America®ionId=811531152953708544&latLong=42.55483%2C-73.16379&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FAshuwillticook-Rail-Trail-Private-Vacation-Homes.d811531152953708544-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FAshuwillticook-Rail-Trail-Private-Vacation-Homes.d811531152953708544-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Ashuwillticook Rail Trail Hotel Reviews ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Great" [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Everything was great. " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "Yes" [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Everything was perfect!!!! Check in quick, staff so helpful. Room perfect!" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Wonderful Experience " [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Nice place to stay, off season. Price was very reasonable. Room was comfortable, (1st floor, Building 5), entire building was very quiet, hardly anyone on the property. Nice amenities, but we only walked through, did not use (pool, locker rooms, hot tub, fire pit). Room was nicely appointed and comfortable. Gas fireplace worked well, hot water was plentiful, water pressure was good. Kitchen was stocked with just about anything you'd need to cook simple meals. Great option when in the area, would recommend and would stay again." [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Wonderful stay, as usual. I have business in the Pittsfield area, 3 or 4 times a year and wouldn’t think of staying anywhere else. Quiet, comfortable….staff is always helpful and friendly….restaurant in the building is just another plus." [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Howard Johnson by Wyndham Lenox](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg) ### Howard Johnson by Wyndham Lenox 10/10 Excellent "The room was clean, comfortable and the staff was friendly. For those who are afraid of vermin, there was NO SIGNS whatsoever of either bugs or other vermin.. It was CLEAN. This is a place that is no frills, but for what you're paying for you get a lot, and a comfortable place to rest your head. We would absolutely go back when we're visiting the Pittsfield area." [](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Good" [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ## Find out more about Ashuwillticook Rail Trail ## Ashuwillticook Rail Trail Vacation Homes information | Number of reviews | 213 | | --- | --- | | Accommodation | 314 Vacation Homes | | Lowest Price | CA $340 | | Highest Price | CA $1,471 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [B&B in Berkshire County](https://www.expedia.ca/Berkshire-County-Bed-And-Breakfast.d553248635083901436-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Berkshire County](https://www.expedia.ca/Berkshire-County-Chalets.d553248635083901436-aaChalets.Travel-Guide-Accommodation) - 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