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Check prices for these dates

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8 Aug - 10 Aug
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29 Aug - 31 Aug
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26 Sept - 28 Sept

Featured Apartments in The Berkshires and around

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
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 €187
includes taxes & fees
6 Aug - 7 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

9.6 out of 10, Exceptional, (7)
"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 €237
includes taxes & fees
1 Sept - 2 Sept
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
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, (15)
"Lovely location to get away for the holidays. Location was clean and comfy. Communication with the property manager was easy and they were very helpful when our car got stuck in the snow."
Vacation Rental Home in the Berkshires!
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
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

7.8 out of 10, Good, (10)
"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.
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, (6)
"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 €195
includes taxes & fees
3 Aug - 4 Aug
Bright Boho Apt in 18th c Berkshire Farmhouse
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
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
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)
"Stayed one night at one of my favorite ski spots. Will be back again!"
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
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
New Studio In Town, By the Water
Enjoy cooking in this well-equipped kitchen with a microwave, coffee maker, and oven.

New Studio In Town, By the Water

10.0 out of 10, Exceptional, (7)
"Great location, we really enjoyed our stay! "
New Studio In Town, By the Water
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 The Berkshires Hotel Reviews

FairBridge Inn Express

FairBridge Inn Express

8/10 Good
"Will stay at again."
Michael 1-night trip
Posted 1 day ago
FairBridge Inn Express