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."
United States
Sharon K.
The price is €330
includes taxes & fees
12 Jan - 13 Jan
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
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
12 Jan - 13 Jan
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

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 €297
includes taxes & fees
11 Jan - 12 Jan
Florida Mountain Log Cabin

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)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is €239
includes taxes & fees
13 Jan - 14 Jan
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Suite 3 - Quiet and private accommodations in a country setting.

Suite 3 - Quiet and private accommodations in a country setting.
Spencertown
10.0 out of 10, Exceptional, (1)
"Fantastic place to stay!"
United States
James
Suite 3 - Quiet and private accommodations in a country setting.

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
8.8 out of 10, Excellent, (20)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
The price is €324
includes taxes & fees
12 Jan - 13 Jan
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.2 out of 10, Wonderful, (7)
"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)...
United States
Kathy C.
The price is €261
includes taxes & fees
10 Jan - 11 Jan
Family Ski Getaway in the Berkshires

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is €290
includes taxes & fees
10 Jan - 11 Jan
3-bedroom house in beautiful Berkshires, close to amenities!

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.6 out of 10, Exceptional, (24)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is €321
includes taxes & fees
15 Jan - 16 Jan
Near Tanglewood: Historic Summer Retreat

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (1)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is €370
includes taxes & fees
12 Jan - 13 Jan
Riverbend Berkshire East Basecamp - 3 bedrooms available

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.4 out of 10, Exceptional, (3)
"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
Sarah D.
The price is €404
includes taxes & fees
11 Jan - 12 Jan
Sun Filled Lenox Retreat - Minutes to Tanglewood!

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
2.0 star property
Stephentown
8.0 out of 10, Very good, (1)
"excellent communication with property manager."
United States
Nancy H.
The price is €495
includes taxes & fees
14 Jan - 15 Jan
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

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 €212
includes taxes & fees
1 Feb - 2 Feb
Sweet Cozy Victorian in Housatonic. Close to everything.

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

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (5)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveller
The price is €353
includes taxes & fees
8 Feb - 9 Feb
The Greylock Cabin

Berkshire East Basecamp - 5 bedroom Winter Vintage Vibe Retreat

Berkshire East Basecamp - 5 bedroom Winter Vintage Vibe Retreat
2.0 star property
Charlemont
The price is €580
includes taxes & fees
11 Jan - 12 Jan
Berkshire East Basecamp - 5 bedroom Winter Vintage Vibe Retreat

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

14mi to Mt. Snow! Arcade, Private Suite, 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 €517
includes taxes & fees
21 Jan - 22 Jan
14mi to Mt. Snow! Arcade, Private Suite, King Bed!

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, (7)
"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
Liz V.
The price is €426
includes taxes & fees
14 Jan - 15 Jan
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (32)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is €571
includes taxes & fees
19 Jan - 20 Jan
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is €484
includes taxes & fees
9 Jan - 10 Jan
Artists’ Hideaway in Old Chatham
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

Find out more about Ashuwillticook Rail Trail

Ashuwillticook Rail Trail Holiday Homes information

Number of reviews
162
Accommodation
314 Holiday Homes
Lowest Price
€212
Highest Price
€571

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