Name: Vacation Village in the Berkshires
Price range: $123 total
Rating: 8.8

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

$111 nightly

$124 total

May 26 - May 27

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

Berkshires Untold

194 Pittsfield Rd Lenox MA

$105 nightly

$117 total

May 12 - May 13

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

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

$110 nightly

$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 ...

8.8/10 Excellent! (2,351 reviews)

I loved my stay at the resort! The view was beautiful, my room was clean, and the staff were nice. I had trouble with my door, and they sent someone quickly to fix it.

Reviewed on May 8, 2026

See all 1,013 properties in Cheshire

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

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 ...

8.8/10 Excellent! (2,351 reviews)

I loved my stay at the resort! The view was beautiful, my room was clean, and the staff were nice. I had trouble with my door, and they sent someone quickly to fix it.

Reviewed on May 8, 2026

The Ponds at Foxhollow

3 Foxhollow Drive Route 7 Lenox MA

Stay at this aparthotel in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and National Shrine of the ...

8.6/10 Excellent! (141 reviews)

I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. ...

Reviewed on Feb 9, 2026

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Whitingham VT

Stay at this apartment in Whitingham. Enjoy free breakfast, a sauna, and laundry facilities. Popular attractions Harriman Reservoir and Readsboro Community Library ...

9.6/10 Exceptional! (5 reviews)

A beautiful, clean, and cozy stay. The modern space was bright and well-equipped with everything we needed, and the hot tub made it especially relaxing.

Reviewed on Apr 24, 2026

See all properties in Cheshire

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.