Chester, MA

Travel Guide

A river flowing through a forest with autumn-colored trees.
A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.
A bridge over a calm river with trees and buildings in the background.
A stone bridge over a calm river with autumn leaves and trees.
A snow-covered forest with a narrow stream running through it.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is NT$2,518 per night from Dec 6 to Dec 7
NT$2,518
NT$3,545 total
Dec 6 - Dec 7
includes taxes & 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 ...
Berkshire Mountain Lodge
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
The price is NT$3,865 per night from Nov 29 to Nov 30
NT$3,865
NT$4,522 total
Nov 29 - Nov 30
includes taxes & fees
Book a stay at this spa hotel in Holyoke. Enjoy free breakfast, a full-service spa, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
D. Hotel Suites & Spa
Blue A Modern Hotel, an Ascend Collection Hotel

Blue A Modern Hotel, an Ascend Collection Hotel

2.5 out of 5
1080 Riverdale St West Springfield MA
The price is NT$3,318 per night from Nov 26 to Nov 27
NT$3,318
NT$3,798 total
Nov 26 - Nov 27
includes taxes & fees
Book a stay at this business-friendly hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions MGM Springfield ...
Blue A Modern Hotel, an Ascend Collection Hotel
See all 876 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

Berkshire Mountain Lodge

3 out of 5
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 ...
Berkshire Mountain Lodge
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
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 ...
8.4/10 Very Good! (157 reviews)
"liked it was clean . furniture is dated. Roads need repair . too many potholes"

Reviewed on 2026/11/2

The Ponds at Foxhollow
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.

Stay near popular Chester attractions

Chester Town Hall

You can get tickets for a performance at Chester Town Hall during your trip to Chester. Wander the lakeside and forest in this relaxing area.
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Cities near Chester

A snow-covered forest with a stone bridge in the background.

Middlefield