A paved path flanked by trees with autumn foliage, a wooden fence, and a clear blue sky.

Holiday Homes in Ashuwillticook Rail Trail

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Ashuwillticook Rail Trail holiday homes

A heated pool

1. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is AU$817
includes taxes & fees
1 Sept - 2 Sept
Comfortable Berkshires retreat on mtn resort, SISO
Dining

2. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (6 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is AU$292
includes taxes & fees
16 Aug - 17 Aug
Cozy Home in Pownal VT
Coffee/tea maker, fridge, microwave, oven

3. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is AU$296
includes taxes & fees
9 Aug - 10 Aug
NEW RENO - Chalet-style farm loft near Tanglewood
Outdoor dining

4. 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!
Pittsfield
8.4 out of 10, Very good, (9 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
Liz V.
The price is AU$786
includes taxes & fees
10 Aug - 11 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Coffee/tea maker, fridge, microwave, stovetop

5. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (6 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is AU$798
includes taxes & fees
9 Aug - 10 Aug
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Pool

6. 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, (74 reviews)
"Helpful host, lovely condo. Great location. Clean, tons of games and movies in unit. Also plenty of coffee pods included!"
United States
Christy F.
The price is AU$916
includes taxes & fees
12 Aug - 13 Aug
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Exterior

7. Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.

Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.
Hinsdale
10.0 out of 10, Exceptional, (9 reviews)
"Kendra was an excellent host! Very nice and welcoming and answered questions promptly. The house was beautiful and the country setting and lake was picturesque. "
United States
Joseph L.
The price is AU$841
includes taxes & fees
10 Aug - 11 Aug
Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.
Property grounds

8. Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (5 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is AU$654
includes taxes & fees
28 Aug - 29 Aug
Riverbend Berkshire East Basecamp - 3 bedrooms available
Property grounds

9. Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views

Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Stamford
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful area and views of mountains, very gracious host "
United States
Donna E.
The price is AU$461
includes taxes & fees
17 Aug - 18 Aug
Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Interior

10. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (6 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$581
includes taxes & fees
8 Sept - 9 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Exterior

11. The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful cabin in a beautiful location. Host is amazing, very responsive. "
United States
Anonymous traveller
The price is AU$681
includes taxes & fees
7 Sept - 8 Sept
The Greylock Cabin
TV, DVD player, books, video library

12. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is AU$365
includes taxes & fees
8 Sept - 9 Sept
1800s Carriage house in Berkshires / Hudson Valley
Exterior

13. North Getaway Cottage

North Getaway Cottage
Williamstown
8.8 out of 10, Excellent, (27 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is AU$653
includes taxes & fees
31 Aug - 1 Sept
North Getaway Cottage
Exterior

14. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (35 reviews)
"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 AU$511
includes taxes & fees
13 Aug - 14 Aug
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Outdoor spa tub

15. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AU$572
includes taxes & fees
8 Sept - 9 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Dining

16. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is AU$851
includes taxes & fees
10 Aug - 11 Aug
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Exterior

17. Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 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
Hunter
The price is AU$620
includes taxes & fees
13 Aug - 14 Aug
Two Brooks Lodge
Outdoor dining

18. Ski's The Day: Winsome 3-bedroom mountain townhome with AC in Jiminy Peak

Ski's The Day: Winsome 3-bedroom mountain townhome with AC in Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"good"
United States
Ismael
Ski's The Day: Winsome 3-bedroom mountain townhome with AC in Jiminy Peak
Smart TV

19. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is AU$622
includes taxes & fees
19 Aug - 20 Aug
stylish Berkshires Retreat
Exterior

20. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is AU$761
includes taxes & fees
1 Sept - 2 Sept
1789 Shaker Farmhouse in Berkshires/Hudson Valley
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
222
Accommodation
322 Holiday Homes
Lowest Price
AU$292
Highest Price
AU$916

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