Search Cherry Plain Cottage Rentals from CA $1,483

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Browse Select Cherry Plain Cottages

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

2.0 star property
9.0 out of 10, Wonderful, (4)
"Cozy, serene and bucolic waterfront hideaway within driving distance of Tanglewood, Shakespeare & Company, Jacob's Pillow and all the wonderful food and cultural Berkshire gems! Julie and Russ were amazing hosts. Great communication and wonderful restaurant and museum suggestions. Definitely planning another long weekend retreat!"
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

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

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (111)
"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

Entire cottage in Berkshire Villiage

3.0 star property
9.6 out of 10, Exceptional, (5)
"The cottage was clean and as described. The street was very quiet."
Entire cottage in Berkshire Villiage

Cozy cottage with pool, walking distance to lake

10.0 out of 10, Exceptional, (15)
"The house was very convenient to anywhere we wanted to go. We even had 5 deer welcome us the first night. House was very comfortable and we loved it."
Cozy cottage with pool, walking distance to lake

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (4)
"We stayed with family and friends and loved all of the offerings from the dock, fire pit and quiet neighborhood."
Lake Views & Dock Access - Pittsfield Cottage!

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

10.0 out of 10, Exceptional, (5)
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!

Berkshires farm, 30+ guests, 50 acres

2.0 star property
The price is CA $1,483
CA $2,475 total
includes taxes & fees
Sep 9 - Sep 10
Berkshires farm, 30+ guests, 50 acres

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!

Expansive Upstate Home w/ Home Theater!

3.0 star property
Expansive Upstate Home w/ Home Theater!

Spacious Home w/ Yard & Patio, 2 Mi to Dtwn Troy

3.0 star property
Spacious Home w/ Yard & Patio, 2 Mi to Dtwn Troy

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3.0 star property
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

Chic Troy Home Near Downtown, 9 Mi to Albany!

3.0 star property
8.0 out of 10, Very good, (1)
Chic Troy Home Near Downtown, 9 Mi to Albany!

Modern Home Overlooking Mt. Greylock, Williamstown!

Modern Home Overlooking Mt. Greylock, Williamstown!

Cozy Berkshire cottage with fireplace.

9.8 out of 10, Exceptional, (25)
"Very nice house. Owners very helpful."
Cozy Berkshire cottage with fireplace.

Plan your Berkshires by the lake

Plan your Berkshires by the lake

Eclectic Troy Home w/ Hot Tub - Pet Friendly!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This place is awesome. We weren't there much as it was parents weekend for RPI but it was so great to come back to a house with a hot tub and sauna. I thought we would use the pool table but the weekend ended up too busy to invite friends over. Super comfortable and beautiful."
Eclectic Troy Home w/ Hot Tub - Pet Friendly!

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

Berkshire Hideaway w/ Fire Pit & Playground!

3.0 star property
Berkshire Hideaway w/ Fire Pit & Playground!
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 Cherry Plain Hotel Reviews