Title: Ashuwillticook Rail Trail Vacation Home Rentals from CA $366: 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) ![The Ashuwillticook Rail Trail](https://images.trvl-media.com/place/811531152953708544/1c2ab733-2998-46b6-94e0-15c0716f2da6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/811531152953708544/1c2ab733-2998-46b6-94e0-15c0716f2da6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 In two weeks [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=811531152953708544&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=811531152953708544&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=811531152953708544&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=811531152953708544&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Ashuwillticook Rail Trail vacation homes ![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/aac07fd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/e8d7246a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/010523ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat [](https://www.expedia.ca/Bennington-Hotels-Two-Brooks-Lodge.h61478133.Hotel-Information) Bennington 8.6/10 Excellent (34 reviews) "The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Malika R. CA $137 CA $372 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Bennington-Hotels-Two-Brooks-Lodge.h61478133.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/8de4c71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/00cc85e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/43b40eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/6b5af50f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Near Tanglewood: Historic Summer Retreat [](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information) New Lebanon 9.4/10 Exceptional (26 reviews) "Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul S. CA $148 CA $462 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information) ![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) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/4e64ac0e.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/106000000/105240000/105230400/105230373/8c55822c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/af01e53f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine [](https://www.expedia.ca/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information) Sherwood Forest 9.6/10 Exceptional (10 reviews) "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 $219 CA $540 total includes taxes & fees Jan 27 - Jan 28 [](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/91000000/90260000/90251100/90251080/6c6cf45f.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) ![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/972c3b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/5dc2bebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Florida Mountain Log Cabin [](https://www.expedia.ca/North-Adams-Hotels-Florida-Mountain-Log-Cabin.h90251080.Hotel-Information) Florida 10/10 Exceptional (4 reviews) "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 $252 CA $464 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/North-Adams-Hotels-Florida-Mountain-Log-Cabin.h90251080.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) ### Riverbend Berkshire East Basecamp - 3 bedrooms available [](https://www.expedia.ca/Charlemont-Hotels-Riverbend-Berkshire-East-Basecamp-3-Bedrooms-Available.h120461825.Hotel-Information) Charlemont 10/10 Exceptional (2 reviews) "Very nice house and the stay was unproblematic!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Noah K. CA $219 CA $583 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Charlemont-Hotels-Riverbend-Berkshire-East-Basecamp-3-Bedrooms-Available.h120461825.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/126000000/125190000/125189700/125189667/f4819412.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/126000000/125190000/125189700/125189667/2b612985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/126000000/125190000/125189700/125189667/74d8d7b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/126000000/125190000/125189700/125189667/e9ba60b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Home in Pownal VT [](https://www.expedia.ca/Pownal-Hotels-Cozy-Home-In-Pownal-VT.h125189667.Hotel-Information) Pownal CA $141 CA $273 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Pownal-Hotels-Cozy-Home-In-Pownal-VT.h125189667.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/eab00089.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) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/6cb471c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/3d81b129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 14mi to Mt. Snow! Arcade, Private Suite, King Bed! [](https://www.expedia.ca/Whitingham-Hotels-14mi-To-Mt-Snow-Arcade.h100720354.Hotel-Information) Whitingham 10/10 Exceptional (14 reviews) "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 $297 CA $730 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Whitingham-Hotels-14mi-To-Mt-Snow-Arcade.h100720354.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/f0ba5959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/23a17279.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/6d1211ce.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) ### Historic Berkshires Home Near Tanglewood, Trails & Wineries [](https://www.expedia.ca/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information) Lebanon Springs 9.0/10 Wonderful (21 reviews) "Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wendy D. CA $184 CA $508 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/9bc69856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/c41e9570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/38d4cb32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/4be6f104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck [](https://www.expedia.ca/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122156037.Hotel-Information) Stephentown 8.0/10 Very good (1 review) "excellent communication with property manager." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy H. CA $240 CA $772 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122156037.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/79000000/78260000/78257600/78257590/b090eb5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78260000/78257600/78257590/277bbd12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78260000/78257600/78257590/ea15296d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78260000/78257600/78257590/7ecad611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Suite 3 - Quiet and private accommodations in a country setting. [](https://www.expedia.ca/Quiet-And-Private-Accommodations-In-A-Country-Setting.h78257590.Hotel-Information) Spencertown 10/10 Exceptional (1 review) "Fantastic place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $292 CA $373 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Quiet-And-Private-Accommodations-In-A-Country-Setting.h78257590.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/c7eb5681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic House](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/8c452d97.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) ![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) ### Two Brooks Lodge [](https://www.expedia.ca/Bennington-Hotels-Two-Brooks-Lodge.h83780792.Hotel-Information) Bennington 4.8/10 (3 reviews) "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 detail](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/f9227a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/3bbdf637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/411deb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/079bb1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3-bedroom house in beautiful Berkshires, close to amenities! [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information) Pittsfield CA $288 CA $470 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/cd1323be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/d3c8327e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/25e02c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/412632db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sun Filled Lenox Retreat - Minutes to Tanglewood! [](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information) Lee 9.6/10 Exceptional (4 reviews) "The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah D. CA $247 CA $627 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/3bd0d6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/399488d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/c34ecca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/8b16599a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sweet Cozy Victorian in Housatonic. Close to everything. [](https://www.expedia.ca/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.Hotel-Information) Housatonic 10/10 Exceptional (3 reviews) "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 $185 CA $366 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/f2b309c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/c5e9caf1.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) ### The Greylock Cabin [](https://www.expedia.ca/North-Adams-Hotels-True-Cabin-In-The-Woods-New-Log-Cabin-With-View-Of-Mt-Greylock.h119137863.Hotel-Information) Florida 10/10 Exceptional (5 reviews) "Wonderful view, peaceful quiet area, cosy cabin." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $324 CA $555 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/North-Adams-Hotels-True-Cabin-In-The-Woods-New-Log-Cabin-With-View-Of-Mt-Greylock.h119137863.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/055ed8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/cc4451e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, electric kettle](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/52345b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Ski Getaway in the Berkshires [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) Great Barrington 9.4/10 Exceptional (8 reviews) "Close to a great bakery and near to a farm market and shopping mall. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cristine C. CA $277 CA $405 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/w1419h960x21y0-4ecf9f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/768d59cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/68e2333c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/4fb2bcba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Artists’ Hideaway in Old Chatham [](https://www.expedia.ca/Old-Chatham-Hotels-Artists-Hideaway-In-Old-Chatham.h121082559.Hotel-Information) Old Chatham CA $221 CA $700 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Old-Chatham-Hotels-Artists-Hideaway-In-Old-Chatham.h121082559.Hotel-Information) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/123000000/122230000/122227300/122227227/9f36ff80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122230000/122227300/122227227/8d6ee530.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/123000000/122230000/122227300/122227227/9751d742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122230000/122227300/122227227/fc000043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Five Bedroom Berkshire East Basecamp - Winter Vintage Vibe Retreat [](https://www.expedia.ca/Charlemont-Hotels-1920s-Inspired-Spacious-5-Bedroom-Home-Minutes-To-Berkshire-East.h122227227.Hotel-Information) Charlemont 10/10 Exceptional (1 review) "What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason F. CA $422 CA $962 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Charlemont-Hotels-1920s-Inspired-Spacious-5-Bedroom-Home-Minutes-To-Berkshire-East.h122227227.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/bdc7550f.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) ![Exterior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/3fc8dc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/811d3663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions! [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) Pittsfield 7.8/10 Good (7 reviews) "The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Liz V. CA $369 CA $678 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/2802a7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/20ff0e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/f0716890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/58aa3713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Barn Retreat — All-Season Escape Awaits! [](https://www.expedia.ca/East-Chatham-Hotels-Spectacular-Barn-With-1-Bedroom-1-Loft.h108908975.Hotel-Information) East Chatham 10/10 Exceptional (2 reviews) "Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy S. CA $459 CA $856 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/East-Chatham-Hotels-Spectacular-Barn-With-1-Bedroom-1-Loft.h108908975.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=2026-02-08&endDate=2026-02-09®ionId=811531152953708544&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## 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=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&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=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&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=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&lodging=CABIN) 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=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&lodging=VILLA) 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=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&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=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&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=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&lodging=VACATION_HOME) 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=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&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 Express & Suites Pittsfield - Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG 10/10 Excellent "room was very nice " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "The room was large, clean and comfortable. The breakfast was good and the staff was great. The hotel is a little bit quaint which I enjoy and why I go there. The only issue was the shower took a while for the water to heat up." [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Beautiful unique property! Very clean room and very friendly staff" [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.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 "Room is great for families. Bit dated but clean and spacious." [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Great stay. Comfortable hotel and very friendly staff. Restaurant is very good. " [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Knotty Pine](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/439bea3f_y.jpg) ### Knotty Pine 10/10 Excellent "The staff was very responsive, we had to check in late and the process was easy. " [](https://expedia.ca/Bennington-Hotels-Knotty-Pine.h119106200.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "The staff is super friendly and accommodating. The location is quiet. We stayed during the winter, but the lake view from the restaurant and breakfast area were really nice. The hotel was well kept and clean. We’ll definitely stay there again. " [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Clean, great location near Bosquet Mountain and grocery store, spacious condo, easy. " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.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 "generally good" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ## Find out more about Ashuwillticook Rail Trail ## Ashuwillticook Rail Trail Vacation Homes information | Number of reviews | 131 | | ----------------- | ------------------ | | Accommodation | 314 Vacation Homes | | Lowest Price | CA $366 | | Highest Price | CA $856 | ## 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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