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

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## 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)

![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/51a25809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/83d3f833_edited_d758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

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 $530 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)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/347359ba.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)

![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)

### Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

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)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/ade792b0.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)

![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)

### Florida Mountain Log Cabin

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 $476 total

includes taxes & fees

Nov 30 - Dec 1

[](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)

![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)

![Exterior](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/e8d7246a.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)

### Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

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 1 - Dec 2

[](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)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/eca16f90.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/101000000/100730000/100720400/100720354/7ec1e2c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

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 $309

CA $741 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)

![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

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 $512 total

includes taxes & fees

Nov 30 - Dec 1

[](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)

![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)

![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)

![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)

### North Getaway Cottage

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 $633 total

includes taxes & fees

Dec 1 - Dec 2

[](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)

![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)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/59edf6fe.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)

### Pet Friendly Riverfront Home in Great Barrington

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)

![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/3bd0d6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/ac2c5f84.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)

### Sweet Cozy Victorian in Housatonic. Close to everything.

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 $190

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)

![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](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/106aa7f3.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)

### Two Brooks Lodge

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)

![Property grounds](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/11a36f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/184c6f2c.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)

### Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

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 $371

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)

![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/f2b309c8.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)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/6616eba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Greylock Cabin

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 $369

CA $614 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)

![Exterior](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/d80b29aa.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)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/76291106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont

CA $225

CA $580 total

includes taxes & fees

Nov 30 - Dec 1

[](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)

![Interior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/adca2c72.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)

![Exterior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/3fc8dc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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 $378

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)

![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)

![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)

### Comfortable Berkshires retreat on mtn resort, SISO

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 $1,017 total

includes taxes & fees

Nov 29 - Nov 30

[](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)

![Fireplace](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/b572a747.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)

### Artists’ Hideaway in Old Chatham

Old Chatham

CA $268

CA $658 total

includes taxes & fees

Dec 1 - Dec 2

[](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)

### Charlemont Chalet - A 15 Acre Private Retreat

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)

![Interior](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/fb68a83f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/636f9a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 5-bedroom house in charming Lee with WiFi

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 $537

CA $1,036 total

includes taxes & fees

Dec 4 - Dec 5

[](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)

![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/ed3ffaa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hancock Village Inn Near Jiminy Peak

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 $827

CA $1,543 total

includes taxes & fees

Dec 1 - Dec 2

[](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.

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## Find vacation rentals that suit your style

Aparthotels

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Cottages

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Condos

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Villas

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Private vacation homes

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Chalets

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## 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 | 212 |
| --- | --- |
| Accommodation | 314 Vacation Homes |
| Lowest Price | CA $340 |
| Highest Price | CA $1,543 |

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-   [Ski Hotels in Pittsfield](https://www.expedia.ca/Pittsfield-Hotels-Ski-Hotel.0-0-d9478-tSkiHotel.Travel-Guide-Filter-Hotels)
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-   [Resorts in Pittsfield](https://www.expedia.ca/Pittsfield-Resort-Hotels.d9478-aaResortHotels.Travel-Guide-Accommodation)
-   [Hotels near Pittsfield Station](https://www.expedia.ca/Pittsfield-Station-Hotels.d6195403.Travel-Guide-Hotels)
-   [Motels in Pittsfield Station](https://www.expedia.ca/Pittsfield-Station-Motels.d6195403-aaMotels.Travel-Guide-Accommodation)
-   [Cheap Hotels in Windsor](https://www.expedia.ca/Windsor-Hotels-Cheap-Hotels.0-0-d6005427-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Hotels with a Pool in Windsor](https://www.expedia.ca/Windsor-Hotels-Hotel-With-Pool.0-0-d6005427-tHotelwithPool.Travel-Guide-Filter-Hotels)
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-   [Windsor Hotels](https://www.expedia.ca/Windsor-Hotels.d6005427.Travel-Guide-Hotels)

-   [Flights to Pittsfield](https://www.expedia.ca/Cheap-Flights-To-Pittsfield.d9478.Travel-Guide-Flights)
-   [Flights to Windsor](https://www.expedia.ca/Cheap-Flights-To-Windsor.d6005427.Travel-Guide-Flights)
-   [Flights from Windsor](https://www.expedia.ca/lp/flights/6005427/flights-from-windsor)
-   [Flights from Bangor (BGR) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/bgr/psf/bangor-to-pittsfield)
-   [Flights from Boston (BOS) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/bos/psf/boston-to-pittsfield)
-   [Flights from Ithaca (ITH) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/ith/psf/ithaca-to-pittsfield)
-   [Flights from Plattsburgh (PBG) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/pbg/psf/plattsburgh-to-pittsfield)
-   [Flights from Phoenix (PHX) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/phx/psf/phoenix-to-pittsfield)
-   [Flights from Richmond (RIC) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/ric/psf/richmond-to-pittsfield)
-   [Flights from Seattle (SEA) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/sea/psf/seattle-to-pittsfield)
-   [Flights from Toronto (YYZ) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/yyz/psf/toronto-to-pittsfield)

-   [Canoe Meadows Wildlife Sanctuary](https://www.expedia.ca/Canoe-Meadows-Wildlife-Sanctuary-Pittsfield.d553248621532665285.Vacation-Attraction)
-   [Hancock Shaker Village](https://www.expedia.ca/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction)

-   [Budget Rental Cars in Pittsfield](https://www.expedia.ca/Budget-Car-Rentals-In-Pittsfield.d9478-c39.Car-Rental-Guide-Suppliers)
-   [Car rental Hancock](https://www.expedia.ca/Car-Rentals-In-Hancock.d112303.Car-Rental-Guide)
-   [Car rentals near Jiminy Peak Mountain Resort](https://www.expedia.ca/Car-Rentals-In-Jiminy-Peak-Mountain-Resort.d553248621532665536.Car-Rental-Guide)
-   [Rental cars Pittsfield Municipal airport](https://www.expedia.ca/Car-Rentals-In-Pittsfield-Municipal.d6031274.Car-Rental-Guide)
-   [Car rental Pittsfield](https://www.expedia.ca/Car-Rentals-In-Pittsfield.d9478.Car-Rental-Guide)

-   [Dalton Vacation Rentals](https://www.expedia.ca/Dalton-Vacation-Rentals.d6911.Travel-Guide-VacationRentals)

-   [Book Vacation Homes in Ashuwillticook Rail Trail on Expedia.com](https://www.expedia.com/Ashuwillticook-Rail-Trail-Private-Vacation-Homes.d811531152953708544-aaPrivateVacationHomes.Travel-Guide-Accommodation)