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Jul 25 - Jul 27
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Browse Select October Mountain State Forest Apartments

Spacious 3-bedroom apartment with WiFi, AC on Main Street Stockbridge
Living area

Spacious 3-bedroom apartment with WiFi, AC on Main Street Stockbridge

Spacious 3-bedroom apartment with WiFi, AC on Main Street Stockbridge
Park Street Penthouse Apartment
Stunning room with a grand piano, staircase, and lush greenery.

Park Street Penthouse Apartment

9.8 out of 10, Exceptional, (6)
"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 CA $175
CA $355 total
includes taxes & fees
Jul 22 - Jul 23
Park Street Penthouse Apartment
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Kitchen features a stainless steel range, oven, and toaster, with dark cabinetry and a wooden floor.

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (26)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Charming Apartment In Berkshire Victorian Home
Staircase leads to a landing with a door and stained glass windows featuring geometric patterns.

Charming Apartment In Berkshire Victorian Home

8.0 out of 10, Very good, (9)
"This adorable place is central to Pittsfield and made it really easy for my daughter and I go get where we needed to be. It’s a clean, great space. We’ll definitely be back!"
Charming Apartment In Berkshire Victorian Home
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.
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
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
Charming 1-bedroom apartment in wonderful Lenox Dale
Stroll up to this charming home, featuring a beautifully maintained yard with a variety of plants and a prominent sunflower.

Charming 1-bedroom apartment in wonderful Lenox Dale

10.0 out of 10, Exceptional, (6)
"Very comfortable, spacious, and well equipped. A perfect place to stay while attending a wedding in Lenox"
Charming 1-bedroom apartment in wonderful Lenox Dale
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
9.6 out of 10, Exceptional, (5)
"Clean and well stock"
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
The Brooks Motel: Exceptional Suite
Relax in this stylish living room with a grey sofa, side table, and patterned rug, offering a view of the outside through the large window.

The Brooks Motel: Exceptional Suite

7.0 out of 10, Good, (4)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
The price is CA $218
CA $276 total
includes taxes & fees
Jul 21 - Jul 22
The Brooks Motel: Exceptional Suite
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
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
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Surrounded by lush greenery, this charming inn features a traditional gabled roof and a welcoming entrance.

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

10.0 out of 10, Exceptional, (3)
"Condo in great location for skiing and really in good shape. Nicely decorated. Kids loved the moose toy. Kitchen had everything we needed. Perfect winter break for us. "
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Relax in this inviting living area with a sofa, chair, and dining table, surrounded by framed artwork and lush views.

Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails

2.0 star property
10.0 out of 10, Exceptional, (1)
"This location was perfect for hiking the AT. The trail is only a few feet from the front door. The backyard is very nice, and they had chairs and tables to sit out. The apartment was a nice size for two people. There was no tv, so we used our computer. The kitchen was great to have since we didn't plan on eating out every night. There are plenty of restaurants in the area. The hosts were great and very responsive. The fall colors made the trip extra special."
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
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
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
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

Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Experience the charm of John Harvard's Restaurant & Brewery, featuring a traditional facade with a central entrance and a relaxing pool area.

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.6 out of 10, Exceptional, (26)
"We really enjoyed our stay it was a very nice place for a family."
The price is CA $373
CA $645 total
includes taxes & fees
Aug 16 - Aug 17
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Relax by the clear pool surrounded by lounge chairs and umbrellas, set amidst a peaceful natural environment.

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

10.0 out of 10, Exceptional, (1)
"This is a great on mountain place at Jiminy. We loved all of the fun and games contained within the room. Owner was very helpful with information about the resort and the surrounding area. Will definitely stay there again."
The price is CA $155
CA $337 total
includes taxes & fees
Jul 23 - Jul 24
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
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 October Mountain State Forest Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"We enjoyed the unique character and flavor of the hotel!"
Brad 3-night trip
Posted 2 days ago
Berkshires Untold