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Browse Select Pittsfield Apartments

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

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

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

9.4 out of 10, Exceptional, (81)
"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!

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 $187
CA $371 total
includes taxes & fees
Aug 11 - Aug 12
Park Street Penthouse Apartment

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!

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!

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.

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.

A Haven of Rest in Stately Historic Home Cozy 2nd floor Suite.

10.0 out of 10, Exceptional, (26)
"Wonderful place to stay. Highly recommend. Like something out of a hallmark movie"
A Haven of Rest in Stately Historic Home Cozy 2nd floor Suite.

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

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

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

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 $220
CA $276 total
includes taxes & fees
Aug 3 - Aug 4
The Brooks Motel: Exceptional Suite

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

Tiny House 2.5 hrs NYC and Boston Waterfront WIFI

9.6 out of 10, Exceptional, (24)
"Peaceful property, very responsive owners. The home was impeccably clean. Perfect for 2 adults, 1 teen, and a medium sized dog. "
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI

New Studio In Town, By the Water

10.0 out of 10, Exceptional, (7)
"Great location, we really enjoyed our stay! "
The price is CA $166
CA $356 total
includes taxes & fees
Aug 5 - Aug 6
New Studio In Town, By the Water

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

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

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

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

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 Pittsfield Hotel Reviews