Name: Berkshire Mountain Lodge
Price range: $139 total

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

$142 nightly

$158 total

Sep 7 - Sep 8

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! (2,135 reviews)

"Everything and everyone was great. Thank u so much"

Reviewed on Aug 27, 2026

The Yankee Inn

461 Pittsfield Rd Lenox MA

$152 nightly

$170 total

Sep 27 - Sep 28

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 ...

9.2/10 Wonderful! (1,001 reviews)

"One of the quietest rooms we have ever stayed in. The location was very convenient to sites in both Lenox and Stockbridge."

Reviewed on Aug 27, 2026

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

$125 nightly

$139 total

Aug 31 - Sep 1

Total with taxes and fees

Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...

See all 875 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.

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...

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 The Mount are located ...

8.6/10 Excellent! (147 reviews)

"A very tired looking property. A strange, musty oder inside. Water pressure was awful."

Reviewed on Aug 24, 2026

Private Island - Largest Fresh Water Reservoir in Mass

Otis MA

Stay at this cottage in Otis. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Larkum Pond and Otis Reservoir are located nearby.

8.6/10 Excellent! (10 reviews)

"A fantastic location with a great view of the lake, lots of friendly people, quaint, nice town. Gonna go back."

Reviewed on Jul 23, 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.