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
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
Fully refundableReserve now, pay when you stay
The price is AED 406 per night from Dec 2 to Dec 3
AED 406
AED 460 total
2 Dec - 3 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! (1,304 reviews)
Very sweet staff mf accommodating

Reviewed on 24 November 2025

La Quinta Inn & Suites by Wyndham Springfield MA
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 3 to Dec 4
AED 314
AED 365 total
3 Dec - 4 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! (2,259 reviews)
the room and staff were great

Reviewed on 23 November 2025

D. Hotel Suites & Spa
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! (763 reviews)
The room was very clean, appreciated the friendly and helpful staff. Well stocked kitchen, super close to grocery stores and restaurants.

Reviewed on 21 November 2025

Get rates
Berkshire Mountain Lodge
See all 845 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 ...
9.6/10 Exceptional! (228 reviews)
Amazing house . Only stayed for a weekend but was very impressed how clean comfortable this place was. Beautiful yard with great fire pit . Nice doc to sit on. We actually went out on the kayak which was amazing. Did a lot of walking as well. Will definitely be back thank you Justin.

Reviewed on 10 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