Holiday Homes in Ashuwillticook Rail Trail

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Check prices for these dates

Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec
In one month
19 Dec - 21 Dec
In two months
16 Jan - 18 Jan

Featured Holiday Homes in Ashuwillticook Rail Trail and around

TV
Florida Mountain Log Cabin

Florida Mountain Log Cabin

2.0 star property
Florida
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is €299
includes taxes & fees
16 Dec - 17 Dec
Florida Mountain Log Cabin
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

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

Sherwood Forest
10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is €333
includes taxes & fees
19 Nov - 20 Nov
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Smart TV, books
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

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

Sherwood Forest
9.6 out of 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
James D.
The price is €346
includes taxes & fees
24 Nov - 25 Nov
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Fridge, microwave, oven, stovetop
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

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

Bennington
8.6 out of 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
Ransom W.
The price is €239
includes taxes & fees
19 Nov - 20 Nov
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Fridge, microwave, oven, stovetop
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

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

Whitingham
10.0 out of 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
Jacklyn D.
The price is €450
includes taxes & fees
19 Nov - 20 Nov
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs
9.0 out of 10, Wonderful, (19)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is €347
includes taxes & fees
11 Dec - 12 Dec
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Fridge, microwave, oven, stovetop
Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat

New Lebanon
9.4 out of 10, Exceptional, (23)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
Near Tanglewood: Historic Summer Retreat
Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic
10.0 out of 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
Cheryl F.
The price is €214
includes taxes & fees
11 Dec - 12 Dec
Sweet Cozy Victorian in Housatonic. Close to everything.
Exterior
North Getaway Cottage

North Getaway Cottage

Williamstown
9.4 out of 10, Exceptional, (23)
"The cottage was the perfect accommodations for our overnight stay in town for a funeral. Thank you Claudia. "
United States
Mary Alice H.
The price is €393
includes taxes & fees
19 Nov - 20 Nov
North Getaway Cottage
Games room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.0 out of 10, Wonderful, (4)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is €263
includes taxes & fees
19 Nov - 20 Nov
Pet Friendly Riverfront Home in Great Barrington
Panoramic House | Private kitchen
Two Brooks Lodge

Two Brooks Lodge

3.0 star property
Bennington
4.8 out of 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
Hunter
Two Brooks Lodge
Property grounds
Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont
The price is €363
includes taxes & fees
20 Nov - 21 Nov
Riverbend Berkshire East Basecamp - 3 bedrooms available
Fridge, microwave, oven, stovetop
The Greylock Cabin

The Greylock Cabin

Florida
10.0 out of 10, Exceptional, (4)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveller
The price is €383
includes taxes & fees
14 Dec - 15 Dec
The Greylock Cabin
Exterior
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

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

Hancock
9.8 out of 10, Exceptional, (72)
"Great communication. Lots of games for the kids. Comfortable beds. Great living and game room. "
United States
Samuel R.
The price is €485
includes taxes & fees
19 Nov - 20 Nov
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Exterior
Bungalow in the Berkshires

Bungalow in the Berkshires

Lee
10.0 out of 10, Exceptional, (4)
"We had a lovely stay. Easy check in and communication was great. "
United States
Dale G.
The price is €342
includes taxes & fees
4 Dec - 5 Dec
Bungalow in the Berkshires
Fridge, microwave, oven, stovetop
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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

2.0 star property
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is €434
includes taxes & fees
19 Nov - 20 Nov
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
The price is €648
includes taxes & fees
8 Dec - 9 Dec
Comfortable Berkshires retreat on mtn resort, SISO
Outdoor dining
Charlemont Chalet - A 15 Acre Private Retreat

Charlemont Chalet - A 15 Acre Private Retreat

2.0 star property
Charlemont
The price is €588
includes taxes & fees
15 Dec - 16 Dec
Charlemont Chalet - A 15 Acre Private Retreat
Fireplace
Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham

Old Chatham
Artists’ Hideaway in Old Chatham
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is €697
includes taxes & fees
1 Dec - 2 Dec
Spacious 5-bedroom house in charming Lee with WiFi
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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Top Ashuwillticook Rail Trail Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
Frank 1-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Ashuwillticook Rail Trail

Ashuwillticook Rail Trail Holiday Homes information

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