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Cottages in Pittsfield State Forest

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

10.0 out of 10, Exceptional, (1)
"We were staying for an event in Adams and didn't need much... Stepping inside the cottage was a delight!! A great deal of thought and design has gone into making this little old lake cottage, into a lovely, friendly and comfortable place to stay. I hope we will have cause to return. "
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (107)
"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"
Charming historic cottage on scenic road to Mt. Greylock

Cozy Berkshire cottage with fireplace.

9.8 out of 10, Exceptional, (25)
"House and property were beautiful, well stocked and perfectly situated close to everything but also quiet and scenic. Owner was fantastic to deal with. She was helpful and accommodating, even had a sweet card and little gift to welcome us. Would definitely stay here again!! "
Cozy Berkshire cottage with fireplace.

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (2)
"This home is so adorable! Very clean. 4 bedrooms and 2 baths are a plus. Great location...beautiful view of the lake. "
Lake Views & Dock Access - Pittsfield Cottage!

Beachwood Cottage

10.0 out of 10, Exceptional, (3)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
Beachwood Cottage

Heaven Can't Wait, On Beautiful Kinderhook Lake! 4TH OF JULY FIREWORKS ON LAKE!

9.8 out of 10, Exceptional, (83)
"Home our mother's 83rd birthday party cookout at the lake house with a few family members and it was a great day. Everyone loved the house. We enjoyed the stay"
Heaven Can't Wait, On Beautiful Kinderhook Lake! 4TH OF JULY FIREWORKS ON LAKE!

Grandparent’s Cottage 250 steps to the lake

Grandparent’s Cottage 250 steps to the lake

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

2.0 star property
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Cozy cottage with pool, walking distance to lake

10.0 out of 10, Exceptional, (15)
"We spent the weekend for a nearby wedding. Great area. The house was clean and had everything you would want. Good communication with the host. Thanks!"
Cozy cottage with pool, walking distance to lake

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Private Lake Cottage on 3 acres w/350 sq. ft. deck

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

10.0 out of 10, Exceptional, (2)
"Stayed for 3 nights over Presidents Day weekend, and we loved the spot! Recently refreshed with a new kitchen, floors and fixtures, it’s still felt warm and inviting. The electric fire / heater in the living room was well used, and we cooked our meals with the new appliances and well equipped kitchen. Proximity to Great Barrington, Stockbridge, Lenox, Lee, and all of the outdoor adventures (and shopping/restaurants) worked out perfectly, even given the snowy/ice weather. Plenty of space for the...
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

Cottage in the Clouds With Mountain Views

9.4 out of 10, Exceptional, (3)
"A nice place to relax. A bit toasty on warm days but otherwise enjoyed our stay."
Cottage in the Clouds With Mountain Views

Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy

10.0 out of 10, Exceptional, (11)
"Our family rented this property for a long weekend trip and had a great experience. We enjoyed the beauty of the local area, including some great local restaurants and coffee shops. We were snowed in for one day of our trip and enjoyed the coziness of the property and the full kitchen came in clutch to avoid needing to travel during the storm. "
Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy

Cozy Becket Cottage Escape w/ Lake Access!

3.0 star property
Cozy Becket Cottage Escape w/ Lake Access!

Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger

Entire cottage in Berkshire Villiage

3.0 star property
9.4 out of 10, Exceptional, (3)
"The cottage was clean and as described. The street was very quiet."
Entire cottage in Berkshire Villiage

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
Cozy Stockbridge Cabin - Walk to Beach & Lake!

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
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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