Chester, MA

Travel Guide

Photo by Elizabeth Massa Peroulakis
Photo by Elizabeth Massa Peroulakis
Photo by Elizabeth Massa Peroulakis
Photo by Elizabeth Massa Peroulakis
Photo by Chris Addams
Photo by Chris Addams
Photo by Chris Addams
Photo by Chris Addams
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
The price is AED 314 per night from Dec 24 to Dec 25
AED 314
AED 365 total
24 Dec - 25 Dec
includes taxes & 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! (2,273 reviews)
The hotel was great. The biggest thing keeping this from being excellent was that the thermostat in the room didn't work. The fan was set to auto yet the heater kept heating until it was too hot. We had to turn it off at times and it made sleeping uncomfortably hot.

Reviewed on 29 November 2025

D. Hotel Suites & Spa
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 AED 406 per night from Dec 3 to Dec 4
AED 406
AED 460 total
3 Dec - 4 Dec
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! (1,310 reviews)
Generally very good

Reviewed on 1 December 2025

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

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
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! (768 reviews)
When we are out in Pittsfield we always stay at the BML. The rooms are spacious, clean, and comfortable. For the price of a hotel room, you get a small condo. The staff is always friendly and helpful. Stay there, you won't regret it.

Reviewed on 26 November 2025

Get rates
Berkshire Mountain Lodge
See all 844 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

The Ponds at Foxhollow

3 out of 5
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! (134 reviews)
Very good value

Reviewed on 18 November 2025

The Ponds at Foxhollow
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington MA
Stay at this vacation home in Great Barrington. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Monument Mountain Reservation and Art et ...
9.2/10 Wonderful! (5 reviews)
Amazing cosy property. The berkshires are beautiful and Marisa was a great host. Thank you for having us!

Reviewed on 9 November 2025

Pet Friendly Riverfront Home in Great Barrington
Peace and quiet on the lake

Peace and quiet on the lake

Becket MA
Stay at this vacation home in Becket. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
9.4/10 Exceptional! (230 reviews)
The veiws and how peacefull it was

Reviewed on 16 November 2025

Peace and quiet on the lake
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.

Popular places to visit

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.

Chester Town Hall