Chester, MA
Travel Guide
Visit Chester
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
The price is NT$3,428 per night from Jan 14 to Jan 15
NT$3,428
NT$3,982 total
Jan 14 - 2026/1/15
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! (2,242 reviews)
Great room, affordable, and incredibly friendly and accommodating front desk staff. Restaurant is right on site and is fantastic as well!
Reviewed on 2025/12/29
The Red Lion Inn
30 Main Street Stockbridge MA
The price is NT$4,707 per night from Jan 14 to Jan 15
NT$4,707
NT$6,660 total
Jan 14 - 2026/1/15
includes taxes & fees
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (1,002 reviews)
I had always wanted to stay at The Red Lion Inn and decided to treat myself to a one-night stay. Since it was in December I was especially excited to have a fireplace in the room. Sadly, I learned the fireplace didn’t work and that they are renovating some of the systems, but offered no partial refund ...
Reviewed on 2025/12/23
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
The price is NT$2,770 per night from Jan 3 to Jan 4
NT$2,770
NT$3,094 total
Jan 3 - 2026/1/4
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (1,003 reviews)
Did not have breakfast. Wish it was free but the hotel staff was amazing and the valet was great too!
Reviewed on 2025/12/28
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
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! (137 reviews)
Great place
Reviewed on 2025/12/23
Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!
Charlemont MA
Stay at this cottage in Charlemont. Enjoy air conditioning. Popular attractions Hawley Bog Preserve and Berkshire East Ski Resort are located nearby.
10/10 Exceptional! (1 review)
Loved this old home! Record player and records were fun to listen to. Pickle ball across the street was excellent! Well stocked kitchen great for cooking in. I had a tough time with water pressure and temperature but it could have been user error. Beds were comfortable except for the twin, which ...
Reviewed on 2025/10/14
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.
- Ski Butternut
- National Shrine of the Divine Mercy
- Smith College
- Big E
- Bousquet Ski Area
- Holyoke Mall
- Connecticut River
- Lee Premium Outlets
- Norman Rockwell Museum
- Olympia Ice Center
- Colonial Theater
- Smith College Botanic Garden
- Berkshire Botanical Garden
- Goose Pond Reservation
- International Volleyball Hall of Fame
- Maple Corner Farm Cross Country Ski Area
