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 SAR 399 per night from Mar 9 to Mar 10
SAR 399
SAR 463 total
includes taxes & fees
9 Mar - 10 Mar
Stay at this 3-star 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! (2,361 reviews)
"Safe"

Reviewed on 3 March 2025

D. Hotel Suites & Spa
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is SAR 363 per night from Mar 9 to Mar 10
SAR 363
SAR 406 total
includes taxes & fees
9 Mar - 10 Mar
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (511 reviews)
"The restaurant and lounge area is so inviting, and staff is all around excellent."

Reviewed on 2 March 2025

Life House Berkshires
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
The price is SAR 300 per night from Mar 16 to Mar 17
SAR 300
SAR 335 total
includes taxes & fees
16 Mar - 17 Mar
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 ...
9/10 Wonderful! (1,004 reviews)
"This was a very nice little getaway from everyday life. The room was nice and roomy and we loved the fireplace."

Reviewed on 3 March 2025

The Yankee, Trademark Collection by Wyndham
See all 797 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 by Capital Vacations
The Ponds at Foxhollow by Capital Vacations
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 The Mount and Wyndhurst Golf & Club are located ...
8.6/10 Excellent! (120 reviews)
"Very comfortable property in a lovely setting"

Reviewed on 18 December 2024

The Ponds at Foxhollow by Capital Vacations
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
Lanesborough
Stay at this vacation home in Lanesborough. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Crane Museum of Papermaking and Crane ...
9.6/10 Exceptional! (239 reviews)
Bershire get away
"Property was very nice Kirchen could use some additons -starting with a ladle"

Reviewed on 25 January 2025

Berkshire Village Carriage House - Super Private!!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield
Stay at this cabin in Sandisfield. Enjoy a garden, tennis courts, and patios. Popular attractions Otis Ridge and Old Baldy Wildlife Sanctuary are located ...
9.6/10 Exceptional! (35 reviews)
Nice Cabin
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."

Reviewed on 3 January 2025

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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