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 434 per night from Apr 29 to Apr 30
AED 434
AED 504 total
includes taxes & fees
29 Apr - 30 Apr
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! (2,292 reviews)
"Consistently excellent stay- highly recommended Caring and professional staff Super clean rooms each with its own character Great free breakfast Great value !"

Reviewed on 23 April 2025

D. Hotel Suites & Spa
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is AED 392 per night from May 7 to May 8
AED 392
AED 438 total
includes taxes & fees
7 May - 8 May
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! (565 reviews)
"It was an older motel, remodeled recently. It was a mini-vacation, a great place and great food."

Reviewed on 20 April 2025

Life House Berkshires
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 Apr 27 to Apr 28
AED 406
AED 460 total
includes taxes & fees
27 Apr - 28 Apr
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! (1,277 reviews)
"I like the views on the city because i was in 6th floor"

Reviewed on 22 April 2025

La Quinta Inn & Suites by Wyndham Springfield MA
See all 805 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! (120 reviews)
"Very comfortable property in a lovely setting"

Reviewed on 18 December 2024

The Ponds at Foxhollow
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Lee
Stay at this apartment in Lee. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Tanglewood Music Center and Berkshire ...
9.4/10 Exceptional! (54 reviews)
charming, comfortable and conveniently located
"3 day holiday getaway, my husband and our 2 pups. A hike in nearby trails in the woods, enjoyed Lee downtown eateries and shops. Beautiful winter wonderland in the Berkshires. The guest rental was perfect!!! Warm, spacious, comfortable, perfect location."

Reviewed on 18 February 2025

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
The Clearing - Quiet - Close To Nature
The Clearing - Quiet - Close To Nature
Cummington
Stay at this cottage in Cummington. Enjoy free WiFi, private pools, and a garden. Our guests praise the property condition in our reviews. Popular attractions ...
Peaceful
"Thank you for sharing your wonderful home! It had everything we needed including a quiet, peaceful, private, beautiful location, comfortable bed, great books!!, and a well equipped kitchen. We are very grateful you had availability for our Thanksgiving visit with family. Thank you!!"

Reviewed on 2 December 2024

The Clearing - Quiet - Close To Nature
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