Name: The Yankee, Trademark Collection by Wyndham
Price range: $103 total
Rating: 9

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

$127 nightly

$141 total

Feb 10 - Feb 11

Total with taxes and fees

Book a stay at this spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ...

9.2/10 Wonderful! (2,237 reviews)

YES

Reviewed on Feb 5, 2026

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

$121 nightly

$136 total

Mar 11 - Mar 12

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! (826 reviews)

Room was clean and nicely equipped with kitchen. Will return if the future.

Reviewed on Feb 1, 2026

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA

$93 nightly

$103 total

Feb 22 - Feb 23

Total with taxes and fees

Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...

9/10 Wonderful! (1,010 reviews)

The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay.

Reviewed on Feb 5, 2026

See all 851 properties in Chester

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.

The Ponds at Foxhollow

3 Foxhollow Drive Route 7 Lenox MA

Stay at this condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions The Mount and Wyndhurst Golf & Club are located ...

8.4/10 Very Good! (140 reviews)

Condo was a great space. Bathroom walls should be repainted as stains are evident. There were also stains on the couch which I cleaned.

Reviewed on Jan 3, 2026

The Kemble- Built by a US Secretary of State in Lenox

Lenox MA

Book a stay at this family-friendly villa in Lenox. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Ventfort Hall Mansion and Gilded ...

9.8/10 Exceptional! (18 reviews)

We stayed at The Kemble, the historic Lenox estate built by a U.S. Secretary of State, for a large family reunion with 10 adults and 16 children—and it was, without question, the best large-house experience we’ve ever had.We rent a large home every year, and nothing has come close to this. The house ...

Reviewed on Jan 13, 2026

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Lanesborough MA

Stay at this vacation home in Lanesborough. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ...

10/10 Exceptional! (10 reviews)

Perfect spot to get in a few days of skiing at Jiminy. Well stocked with the basics and hot tub was great. Very responsive host.

Reviewed on Jan 18, 2026

See all properties in Chester

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.