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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Browse Select Ashuwillticook Rail Trail Apartments

Charming Apt in 18th c Berkshire Farmhouse
Two single beds with bedside tables and lamps, set against a rustic wooden wall and a textured rug.

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (34)
"The property was perfect for us !! Lots of room and the beds are very comfortable. "
The price is £158
includes taxes & fees
13 Aug - 14 Aug
Charming Apt in 18th c Berkshire Farmhouse
Park Street Penthouse Apartment
Stunning room with a grand piano, staircase, and lush greenery.

Park Street Penthouse Apartment

9.4 out of 10, Exceptional, (8)
"We stayed in this beautiful penthouse for an overnight get away- we both walked in and were just in love. The high ceilings and tons of windows made it so open feeling. Stunning place!"
The price is £204
includes taxes & fees
12 Aug - 13 Aug
Park Street Penthouse Apartment
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Relax in this inviting living room with a comfortable sofa, a lamp, and a TV.

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

9.4 out of 10, Exceptional, (82)
"Nice place, just what we were looking for to stay the weekend. "
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Relax on the inviting porch with a comfortable sofa and armchairs, surrounded by a lush lawn and a charming house.

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (63)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Downtown Gateway to the Berkshires. Walk to Everything.
Exterior detail

Downtown Gateway to the Berkshires. Walk to Everything.

2.0 star property
8.0 out of 10, Very good, (1)
"This cute and cozy apartment was in an excellent location. We were the first guest to stay here and we had a few concerns: the chairs in the kitchen were broken as was a door frame. The command hooks fell off the several times. There was no place to hang clothes and shelves which held the dishes were dirty and dusty as well as appliances. Some coffee and Kleenex would have a nice. The place has the potential to be amazing with a little more attention to details. We have stayed in many, many...
Downtown Gateway to the Berkshires. Walk to Everything.
Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge
Living area

Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge

9.0 out of 10, Wonderful, (2)
"The apartment is in downtown Stockbridge. We were there to aid our son and his fiancee who are traversing the Appalachia Trail. The location was perfect for us. The apartment is complete new and immaculate. It was very comfortable for the four of us. The only reason that the overall review is four not five stars is that the dryer wasn't working and the kitchen had absolutely now supplies or an ice tray. The dryer not working could have been a disaster for us as we needed to clean our son's...
Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge
2-Bdr Apt In Town, By the Water
Relax by the campfire surrounded by lush greenery and a serene forest atmosphere.

2-Bdr Apt In Town, By the Water

9.8 out of 10, Exceptional, (6)
"The apartment was clean, bright and quiet. Comfortable beds, and well equipped kitchen. About 3 minute walk to shops on spring street and a nice spot out back by the Green river. Perfect spot for a visit to Williamstown! "
The price is £224
includes taxes & fees
25 Aug - 26 Aug
2-Bdr Apt In Town, By the Water
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Enjoy cooking in this well-equipped kitchen with a dishwasher, coffee maker, and ample natural light.

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

2.0 star property
9.8 out of 10, Exceptional, (8)
"Clean and well stock"
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Gateway to the Berkshires - Renovated downtown apartment
Stunning fire station with a central tower and symmetrical facade.

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (8)
"Emmy is a great hostess. The apartment is nicely appointed and in a great location to restaurants and shops and attractions in the Berkshires. "
Gateway to the Berkshires - Renovated downtown apartment
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Arrive at the charming Country Inn, surrounded by lush lawns and mature trees, with a welcoming covered porch.

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

9.8 out of 10, Exceptional, (7)
"This property was awesome for our family! Quick walk to the Mountain and all the shops!!! Great family spot!!"
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Bright Boho Apt in 18th c Berkshire Farmhouse
Welcome to Second Drop Farm, where a rustic signpost marks the entrance to a serene countryside setting.

Bright Boho Apt in 18th c Berkshire Farmhouse

9.0 out of 10, Wonderful, (22)
"Really enjoyed our stay"
The price is £167
includes taxes & fees
17 Aug - 18 Aug
Bright Boho Apt in 18th c Berkshire Farmhouse
Vacation Rental Home in the Berkshires!
Relax in the spacious two-story house with a gable roof, featuring a stone patio with fire pit and seating.

Vacation Rental Home in the Berkshires!

9.8 out of 10, Exceptional, (16)
"Lovely cottage with beautiful views"
Vacation Rental Home in the Berkshires!
Charming 2-bedroom apartment in superb Bennington with WiFi
Smart TV, books

Charming 2-bedroom apartment in superb Bennington with WiFi

9.6 out of 10, Exceptional, (4)
"The pictures don’t do the listing justice, much bigger than the puctures suggest. The location is great with minutes away from Main St. (bars restaurants). Robin is also a great host! Really enjoyed our stay look forward to booking again next winter "
Charming 2-bedroom apartment in superb Bennington with WiFi
Lake Whitingham & Mount Snow Area Village Apartment
Stunning garden feature with a carved metal structure amidst lush greenery.

Lake Whitingham & Mount Snow Area Village Apartment

2.0 star property
10.0 out of 10, Exceptional, (1)
"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."
The price is £232
includes taxes & fees
12 Aug - 13 Aug
Lake Whitingham & Mount Snow Area Village Apartment
Heart of Lenox!! - renovated downtown apartment
Welcome to a charming traditional home with a beautiful garden entrance.

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (70)
"Beautiful property in a perfect location for a girls ski weekend getaway! "
Heart of Lenox!! - renovated downtown apartment
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Compact kitchen area with a refrigerator, sink, and countertop featuring various kitchen items.

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (62)
"Great value, so much better than all the touristy motels in the area!"
The price is £158
includes taxes & fees
12 Aug - 13 Aug
Cozy Rustic Apt in 18th c Berkshire Farmhouse
The Penthouse, Downtown Lenox by Evergreen Home
Prepare meals and dine in comfort at this kitchen with a large island and appliances.

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (8)
"Amazing space and location!"
The Penthouse, Downtown Lenox by Evergreen Home
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Experience the charm of a traditional Country Inn, surrounded by lush greenery and mature trees.

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

10.0 out of 10, Exceptional, (8)
"Great location. Howie is very communicative. Wish we could have stayed longer. "
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Available February 17-21 2025. Sleep 8 - 2-bed apt on Jiminy Peak. Ski in/out!
Cozy living area with a stone fireplace, leather sofas, and rustic furniture.

Available February 17-21 2025. Sleep 8 - 2-bed apt on Jiminy Peak. Ski in/out!

Available February 17-21 2025. Sleep 8 - 2-bed apt on Jiminy Peak. Ski in/out!
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
Enjoy a meal at John Harvard's Restaurant & Brewery, surrounded by a tranquil pool area and lush surroundings.

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby

9.0 out of 10, Wonderful, (2)
"Loved our short stay! Very clean, well maintained, and super cozy. Communication was very prompt and pleasant. Would definitely stay again! "
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"This Vacation Village is amazing, returning this week for a little time away. Stayed last week for work and came home and planned a 3 day trip based on the location. "
Andrea 1-night trip
Posted 1 day ago
Vacation Village in the Berkshires