Chester, MA

Travel Guide

Photo by Elizabeth Massa Peroulakis
Photo by Elizabeth Massa Peroulakis
Photo by Chris Addams
Photo by Chris Addams
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
The price is ¥11,677 per night from Oct 19 to Oct 20
¥11,677
¥16,343 total
Oct 19 - Oct 20
includes taxes & fees
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (646 reviews)
"Excellent location. Friendly staff."

Reviewed on Sep 17, 2025

Berkshire Mountain Lodge
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3 out of 5
100 Congress Street, Springfield, MA
The price is ¥17,480 per night from Oct 19 to Oct 20
¥17,480
¥19,831 total
Oct 19 - Oct 20
includes taxes & fees
Book a stay at this family-friendly hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
8/10 Very Good! (1,265 reviews)
"Overall a great stay for a quick business overnight. Downfall was the shower head in bathroom had extremely low water pressure (basically non existent) and made a horrible clunking noise. Perhaps the mixing valve was broken. Found this out in morning of."

Reviewed on Sep 16, 2025

La Quinta Inn & Suites by Wyndham Springfield MA
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 out of 5
1254 Riverdale Street, West Springfield, MA
The price is ¥13,160 per night from Oct 6 to Oct 7
¥13,160
¥15,061 total
Oct 6 - Oct 7
includes taxes & fees
Stay at this hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (1,013 reviews)
"Excellent overall!"

Reviewed on Sep 13, 2025

Red Roof Inn PLUS+ West Springfield
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

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
Stay at this 3-star condo 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! (129 reviews)
"I loved everything about the place. The tv was confusing and kept timing out. Its my new go to place."

Reviewed on Sep 11, 2025

The Ponds at Foxhollow
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Becket
Stay at this cabin in Becket. Enjoy a garden, laundry facilities, and furnished lanais. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
9.6/10 Exceptional! (191 reviews)
"We appreciated how clean and well stocked the cottage was. The owner was very easy to work with. Accurate description of a quiet, secluded get-away in the woods"

Reviewed on Sep 1, 2025

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
Stay at this vacation home in Lee. Enjoy laundry facilities and in-room fireplaces. Popular attractions Tanglewood Music Center and Berkshire Mountain Country ...
Spacious 5-bedroom house in charming Lee with WiFi
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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