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 391 per night from Mar 16 to Mar 17
AED 391
AED 454 total
includes taxes & fees
16 Mar - 17 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! (2,336 reviews)
"Nice, clean hotel. Our room had a bit of freeway noise, especially at night for some reason."

Reviewed on 12 March 2025

D. Hotel Suites & Spa
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 AED 311 per night from Mar 20 to Mar 21
AED 311
AED 356 total
includes taxes & fees
20 Mar - 21 Mar
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 (1,000 reviews)
"Always the place I stay"

Reviewed on 4 March 2025

Red Roof Inn PLUS+ West Springfield
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is AED 355 per night from Mar 27 to Mar 28
AED 355
AED 397 total
includes taxes & fees
27 Mar - 28 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! (521 reviews)
"I’ve place , clean, great bar and restaurant"

Reviewed on 11 March 2025

Life House Berkshires
See all 795 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 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! (119 reviews)
"Very comfortable property in a lovely setting"

Reviewed on 18 December 2024

The Ponds at Foxhollow
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 Jiminy Peak Mountain Resort 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! (36 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