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Holiday Homes in Ashuwillticook Rail Trail
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Our top choices for Ashuwillticook Rail Trail holiday homes
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
The price is NZ$641
includes taxes & fees
4 Jan - 5 Jan 2026
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, DineSherwood 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."
James D.
The price is NZ$672
includes taxes & fees
4 Jan - 5 Jan 2026
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
Tristan e.
The price is NZ$625
includes taxes & fees
4 Jan - 5 Jan 2026
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Foliage Galore! 14mi to Mt. Snow, Arcade, King BedWhitingham
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. "
Jacklyn D.
The price is NZ$1,034
includes taxes & fees
5 Jan - 6 Jan 2026
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Historic Berkshires Home Near Tanglewood, Trails & WineriesLebanon Springs
8.8 out of 10, Excellent, (20)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
Wendy D.
The price is NZ$633
includes taxes & fees
5 Jan - 6 Jan 2026
Riverbend Berkshire East Basecamp - 3 bedrooms available
Riverbend Berkshire East Basecamp - 3 bedrooms availableCharlemont
10.0 out of 10, Exceptional, (1)
"Very nice house and the stay was unproblematic!"
Noah K.
The price is NZ$723
includes taxes & fees
3 Jan - 4 Jan 2026
Family Ski Getaway in the Berkshires
Family Ski Getaway in the BerkshiresGreat Barrington
9.4 out of 10, Exceptional, (6)
"The host was exceptional and so kind. The location was in close proximity to 3 quaint New England small towns whose downtowns had many restaurants and local shops to enjoy-Great Barrington (GB Eats for breakfast), Stockbridge (best shopping) and Lenox (exceptional dinner at Frankie’s Italian). The house looked updated on the outside but inside looked like early 1900s with a hint of Victorian influence. My only caution is for anyone with mobility issues as all 3 bedrooms and the only (very small)...
Kathy C.
The price is NZ$510
includes taxes & fees
3 Jan - 4 Jan 2026
3-bedroom house in beautiful Berkshires, close to amenities!
3-bedroom house in beautiful Berkshires, close to amenities!Pittsfield
The price is NZ$548
includes taxes & fees
12 Jan - 13 Jan 2026
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
Berkshires Untold
10/10 Excellent
Find out more about Ashuwillticook Rail Trail
Ashuwillticook Rail Trail Holiday Homes information
Number of reviews | 94 |
|---|---|
Accommodation | 314 Holiday Homes |
Lowest Price | NZ$510 |
Highest Price | NZ$1,798 |
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