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

Ashuwillticook Rail Trail Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Ashuwillticook Rail Trail holiday rentals

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,706 reviews)
"Very pleased with our stay -great place for the family we will G-d willing return"
United States
Denton
The price is HK$677
HK$842 total
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,173 reviews)
"Our visit was very nice. Facilities were beautiful!"
United States
marilyn
The price is HK$673
HK$927 total
includes taxes & fees
18 Oct - 19 Oct
Berkshire Mountain Lodge
Four people seated at a table with food and drinks, wearing winter sports helmets.

3. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (9 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
The price is HK$840
HK$1,868 total
includes taxes & fees
6 Oct - 7 Oct
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
An outdoor seating area with a fire pit, tables, and chairs.

4. Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Pool

5. 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 HK$1,263
HK$4,240 total
includes taxes & fees
6 Oct - 7 Oct
Comfortable Berkshires retreat on mtn resort, SISO
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

6. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (18 reviews)
"Nice Place"
United States
Tom C.
The price is HK$840
HK$1,868 total
includes taxes & fees
6 Oct - 7 Oct
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

7. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.6 out of 10, Exceptional, (7 reviews)
"Excellent communication with our host and property exactly as described. Easy check in/check out."
United States
Jillian G.
The price is HK$1,144
HK$2,453 total
includes taxes & fees
6 Oct - 7 Oct
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

8. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (15 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
The price is HK$1,138
HK$2,209 total
includes taxes & fees
6 Oct - 7 Oct
Penthouse Apartment on Park Street
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

9. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (34 reviews)
"We were on a girls backpacking trip and this was the perfect location right off the trail to clean up, get some great rest and grab dinner. The people are so friendly in Dalton and this place had everything we needed!"
United States
Allie T.
The price is HK$1,138
HK$2,682 total
includes taxes & fees
2 Nov - 3 Nov
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A rustic wooden interior with shelves stocked with various products, a 'Tree-Free' sign, and a section with bottled beverages.

10. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
A snow-covered outdoor area with a fire pit, tables, and chairs.

11. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is HK$840
HK$1,868 total
includes taxes & fees
6 Oct - 7 Oct
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A Country Inn with a large, welcoming entrance and multiple parking spaces.

12. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Hancock
8.8 out of 10, Excellent, (8 reviews)
"Everything was wonderful…"
United States
Alyne K.
The price is HK$840
HK$1,868 total
includes taxes & fees
6 Oct - 7 Oct
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

13. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (39 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is HK$1,589
HK$3,686 total
includes taxes & fees
6 Oct - 7 Oct
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
"Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping." ...Lina -- "the fire pit and creek are like a private oasis in the backyard." ... Nachama -- ( no firewood fees )

14. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (21 reviews)
"Great place with easy access to town and even better access to a nice spot to hangout by the creek. I will definitely stay here again."
United States
Thomas
The price is HK$1,059
HK$2,375 total
includes taxes & fees
19 Oct - 20 Oct
2-Bdr Apt In Town, By the Water
A kitchen with white cabinets, a wooden dining table, and pendant lights.

15. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is HK$1,797
HK$3,778 total
includes taxes & fees
13 Oct - 14 Oct
A roomy remodeled retreat close to MassMoCA
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

16. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (12 reviews)
"We had a great stay here. Clean, well-equipped, great location. Hope to come back again!"
United States
Tricia
The price is HK$965
HK$2,189 total
includes taxes & fees
4 Nov - 5 Nov
Downtown | Waterfront | Walk to Shops
A living room with a sofa, armchairs, a TV, a fireplace, and a large window.

17. Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Hancock
8.0 out of 10, Very good, (1 review)
"I chose this place at the very last minute. It was all that I expected and wanted and more: two bedrooms with three beds, a comfortable living space, two full bathrooms, kitchen with all the basic necessities, TV in each bedroom and in the living room, a dining table and chairs, an outside porch with table, a big open space, and grill, easy parking and access, quiet, .and access to two pools. The place was well tended: clean, with towels and extras blankets ready. Howard, the owner, checked on...
United States
Cecilia S.
The price is HK$1,250
HK$2,562 total
includes taxes & fees
6 Oct - 7 Oct
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

18. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A two-story blue house with a porch, surrounded by a garden with orange flowers.

19. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (35 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
The price is HK$530
HK$1,121 total
includes taxes & fees
6 Oct - 7 Oct
Getaway Near Mass MoCA, Great Hiking, Scenic Views
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

20. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Hancock
9.6 out of 10, Exceptional, (33 reviews)
"The suite was a great. Comfortable, clean and decorated very nicely. Bed was very comfortable with nice linens and pillows. "
United States
Eileen O.
The price is HK$805
HK$1,820 total
includes taxes & fees
6 Oct - 7 Oct
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashuwillticook Rail Trail Hotel Reviews

Find out more about Ashuwillticook Rail Trail

Search for holiday rentals in Ashuwillticook Rail Trail on Expedia! You can easily find your home rentals, villas, holiday apartments in Ashuwillticook Rail Trail using one of the methods below:

  • View our selection of featured holiday rentals in Ashuwillticook Rail Trail
  • Use the map to find apartments and other holiday homes in the Ashuwillticook Rail Trail neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Ashuwillticook Rail Trail while they last

Look no further and take a look at our great range of rental properties in Ashuwillticook Rail Trail!

Explore a world of travel with Expedia