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
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Ashuwillticook Rail Trail holiday rentals

Lobby

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2,215 reviews)
"I great place to stay!!"
United Kingdom
Maricel
The price is HK$811
HK$991 total
includes taxes & fees
25 Jan - 26 Jan
Vacation Village in the Berkshires
Exterior

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is HK$1,708
HK$1,907 total
includes taxes & fees
25 Jan - 26 Jan
Jiminy Peak Mountain Resort
Property grounds

Apartment in Whitingham

Lake Whitingham & Mount Snow Area Village Apartment
10.0 out of 10, Exceptional, (1 review)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is HK$1,092
HK$2,384 total
includes taxes & fees
26 Jan - 27 Jan
Lake Whitingham & Mount Snow Area Village Apartment
Exterior

Cabin in Charlemont

Bear Creek Cabin
10.0 out of 10, Exceptional, (44 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
The price is HK$3,119
HK$4,668 total
includes taxes & fees
24 Jan - 25 Jan
Bear Creek Cabin
Smart TV, fireplace, books

Holiday Home in Charlemont

Five Bedroom Berkshire East Basecamp - Winter Vintage Vibe Retreat
10.0 out of 10, Exceptional, (1 review)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is HK$2,441
HK$5,558 total
includes taxes & fees
22 Feb - 23 Feb
Five Bedroom Berkshire East Basecamp - Winter Vintage Vibe Retreat
Smart TV, books

Holiday Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
9.6 out of 10, Exceptional, (10 reviews)
"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 HK$1,249
HK$2,954 total
includes taxes & fees
25 Jan - 26 Jan
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Fridge, microwave, stovetop, dishwasher

Apartment in Whitingham

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
10.0 out of 10, Exceptional, (2 reviews)
"as advertised."
United States
Joshua G.
The price is HK$2,772
HK$4,921 total
includes taxes & fees
26 Jan - 27 Jan
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
TV

Holiday Home in Florida

Florida Mountain Log Cabin
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is HK$1,433
HK$2,651 total
includes taxes & fees
28 Jan - 29 Jan
Florida Mountain Log Cabin
Living area

Apartment in Whitingham

Free HOT Breakfast for each guest everyday! Located in charming Whitingham
2.0 star property
The price is HK$2,554
HK$4,546 total
includes taxes & fees
25 Jan - 26 Jan
Free HOT Breakfast for each guest everyday! Located in charming Whitingham
Exterior

Camping in Williamstown

Huttopia Berkshires
1.0 star property
9.4 out of 10, Exceptional, (8 reviews)
"Healthy food too!"
United States
GEORGINA
The price is HK$1,484
HK$1,658 total
includes taxes & fees
3 Feb - 4 Feb
Huttopia Berkshires
WiFi, bed sheets

Apartment in Lanesborough

Cozy Rustic Apt in 18th c Berkshire Farmhouse
9.6 out of 10, Exceptional, (67 reviews)
"What a quaint and comfy place!"
United States
Lori A.
The price is HK$1,053
HK$1,619 total
includes taxes & fees
25 Jan - 26 Jan
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Dining

Holiday Home in Charlemont

Charlemont Chalet - A 15 Acre Private Retreat
2.0 star property
The price is HK$2,865
HK$5,220 total
includes taxes & fees
25 Jan - 26 Jan
Charlemont Chalet - A 15 Acre Private Retreat
Living area

Apartment in Adams

Penthouse Apartment on Park Street
9.6 out of 10, Exceptional, (14 reviews)
"Clean property, easy check in, and the owner was super communicative. "
United States
Amanda W.
The price is HK$904
HK$1,907 total
includes taxes & fees
24 Jan - 25 Jan
Penthouse Apartment on Park Street
Living area

Apartment in Bennington

Green Mountain Getaway
9.6 out of 10, Exceptional, (18 reviews)
"Very clean property. The location was very convenient to the Main Street of Bennington. Easy check in process. Would definitely stay here again! "
United States
Meredith Y.
The price is HK$1,285
HK$2,751 total
includes taxes & fees
25 Jan - 26 Jan
Green Mountain Getaway
Pool

Apartment in Hancock

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "
United States
Jeffrey R.
The price is HK$1,068
HK$2,151 total
includes taxes & fees
26 Jan - 27 Jan
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Fridge, microwave, stovetop, dishwasher

Holiday Home in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
8.0 out of 10, Very good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
The price is HK$1,364
HK$4,332 total
includes taxes & fees
24 Jan - 25 Jan
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
TV, fireplace, DVD player, books

Cottage in New Lebanon

Berkshires farm, 30+ guests, 50 acres
10.0 out of 10, Exceptional, (1 review)
The price is HK$7,165
HK$13,449 total
includes taxes & fees
26 Jan - 27 Jan
Berkshires farm, 30+ guests, 50 acres
TV, fireplace, books

Chalet in Charlemont

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike
2.0 star property
The price is HK$1,759
HK$5,100 total
includes taxes & fees
26 Jan - 27 Jan
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike
Property grounds

Cabin in Hinsdale

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (35 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is HK$1,396
HK$3,450 total
includes taxes & fees
25 Jan - 26 Jan
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Interior

Aparthotel in Spencertown

Suite 4 - Quiet and private accommodations in a country setting.
10.0 out of 10, Exceptional, (3 reviews)
"Happy to have found this lovely place, which is convenient to Tanglewood, pin-drop quiet, and super comfortable. Next time I will avoid VRBO, though, because of its extortionary fees, and book directly with the inn."
United States
jwnyc3
The price is HK$1,661
HK$2,131 total
includes taxes & fees
26 Jan - 27 Jan
Suite 4 - Quiet and private accommodations in a country setting.
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Room is great for families. Bit dated but clean and spacious."
Shannon 3-night trip
Posted 3 days ago
Vacation Village in the Berkshires

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!