Cherry Plain, NY

Travel Guide

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$113 nightly
The price is $126 total per night from May 24 to May 25
$126 total
May 24 - May 25
Total with taxes and fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (925 reviews)
Room very spacious and clean. Full kitchen is a great bonus.

Reviewed on May 4, 2026

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
$100 nightly
The price is $112 total per night from May 25 to May 26
$112 total
May 25 - May 26
Total with taxes and fees
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (932 reviews)
Easy, comfortable and convenient; rooms and public spaces are nice, modern and stylish updates of modest 60s/70s original motel facilities.

Reviewed on May 6, 2026

Berkshires Untold
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$110 nightly
The price is $123 total per night from May 10 to May 11
$123 total
May 10 - May 11
Total with taxes and fees
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
Vacation Village in the Berkshires
See all 652 properties in Cherry Plain
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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
Vacation Village in the Berkshires
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd Williamstown MA
Stay at this campground in Williamstown. Enjoy free parking, breakfast (surcharge), and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
9.4/10 Exceptional! (10 reviews)
Excelente servicio

Reviewed on Mar 8, 2026

Huttopia Berkshires
Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay

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

East Chatham NY
Book a stay at this family-friendly vacation home in East Chatham. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Queechy Lake and Shaker ...
9.2/10 Wonderful! (10 reviews)
My family and my husband and I enjoyed this beautiful house for the Pittsfield Jazz Festival. There was plenty of room for the 5 of us. The house was extremely clean, check in was so easy and the beds were extremely comfortable. We will 100 % be back!

Reviewed on May 5, 2026

Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay
See all properties in Cherry Plain
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.