Chester, MA
Travel Guide
Visit Chester
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $135 total per night from Jan 18 to Jan 19
$135 total
Jan 18 - Jan 19
Total with taxes and 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! (2,266 reviews)
The front staff upon arrival was incredibly kind and accommodating. We loved the pool and hot tub and the quiet, clean room. It was large and had everything we expected. The breakfast was also great- lots of options for everyone in our family! Thank you.
Reviewed on Jan 11, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$130 nightly
The price is $145 total per night from Feb 1 to Feb 2
$145 total
Feb 1 - Feb 2
Total with taxes and fees
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! (810 reviews)
Very comfortable and very close to ski slope and restaurants
Reviewed on Jan 10, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
$98 nightly
The price is $109 total per night from Jan 23 to Jan 24
$109 total
Jan 23 - Jan 24
Total with taxes and 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! (1,004 reviews)
Another good 2 night stay. Did have a slow shower drain but reported that to maintenance and it was fixed right away. Good service. And also the restaurant is quite good featuring an American menu with a Southern emphasis. The parking garage demo is moving quickly by the way. More parking close to ...
Reviewed on Jan 7, 2026
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! (139 reviews)
Condo was a great space. Bathroom walls should be repainted as stains are evident. There were also stains on the couch which I cleaned.
Reviewed on Jan 3, 2026
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Lanesborough MA
Stay at this vacation home in Lanesborough. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ...
10/10 Exceptional! (6 reviews)
Beautiful lake house, isolated enough that you're not in the city, but close access to amenities and good food. The hot tub was an absolutely amazing experience, and Adam was thoughtful with providing instructions on how to use the firepit and outdoor heating as well. Would love to stay here ...
Reviewed on Dec 4, 2025
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Great Barrington MA
Stay at this vacation home in Great Barrington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Ski Butternut and Lake Buel are located ...
10/10 Exceptional! (28 reviews)
The Turning Point stay was excellent in every respect. We had a large group (11) and all had great sleeping locations, some with ensuite bathrooms, all in short distance to them. Kitchen was awesome for large group cooking and service. Nothing lacking! Location great for Great Barrington attractions, ...
Reviewed on Oct 20, 2025
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.
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- Tanglewood Music Center
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- Ski Butternut
- Big E
- Mount Holyoke College
- Eastern States Exposition
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- Holyoke Mall
- Connecticut River
- Norman Rockwell Museum
- Lee Premium Outlets
- The Mount
- Historic Northampton
- Jacob's Pillow
- Olympia Ice Center
- Berkshire Botanical Garden
- Naumkeag Museum
- Colonial Theater
- Wyndhurst Golf & Club
- Ventfort Hall Mansion and Gilded Age Museum
- Berkshire Museum
- International Volleyball Hall of Fame
- Smith College Botanic Garden
- Goose Pond Reservation
- Chicopee Falls Dam
- Lenox Library
