Chester, MA
Travel Guide
Visit Chester
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
$134 nightly
The price is $149 total per night from Mar 30 to Mar 31
$149 total
Mar 30 - Mar 31
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. ...
9.4/10 Exceptional! (2,223 reviews)
We spent a weekend at this hotel. To be honest, I think I was expecting a little better based on the strong reviews. The property was in decent shape but the rooms were incredibly sparse and basic: our bathroom shower curtain liner fell off repeatedly, no ventilation in there, room furniture was ...
Reviewed on Mar 24, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$108 nightly
The price is $120 total per night from Apr 26 to Apr 27
$120 total
Apr 26 - Apr 27
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! (888 reviews)
very clean and friendly staff
Reviewed on Mar 24, 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
$78 nightly
The price is $87 total per night from Mar 29 to Mar 30
$87 total
Mar 29 - Mar 30
Total with taxes and fees
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (880 reviews)
Wonderful place, great toiletries and great friendly staff. We will be back
Reviewed on Mar 22, 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 Tanglewood Music Center and The Mount are located ...
8.6/10 Excellent! (141 reviews)
I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. ...
Reviewed on Feb 9, 2026
Peace and quiet on the lake
Becket MA
Stay at this vacation home in Becket. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
9.6/10 Exceptional! (234 reviews)
Host was great! Quick communication. Place is a gem for peace and tranquility! The home is beautiful with great view.
Reviewed on Feb 18, 2026
Family Ski Getaway in the Berkshires
Great Barrington MA
Stay at this vacation home in Great Barrington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Monument Mountain Reservation and Art ...
9/10 Wonderful! (12 reviews)
Loved our time here. It was a very cozy set up for a snowy week away, with a pellet stove, an ample amount of puzzles stocked in the house, and the surprise perk of Studley, a 12 year old cuddle machine of a cat who lives here and provided great company. The host was very responsive to all of my ...
Reviewed on Mar 4, 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.
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
- National Shrine of the Divine Mercy
- Mount Holyoke College
- Norman Rockwell Museum
- Big E
- Holyoke Mall
- Ski Butternut
- Smith College
- Eastern States Exposition
- The Mount
- Lee Premium Outlets
- Jacob's Pillow
- Bousquet Ski Area
- Historic Northampton
- Connecticut River
- Naumkeag Museum
- Wyndhurst Golf & Club
- Berkshire Botanical Garden
- Olympia Ice Center
- Shakespeare and Company
- Ventfort Hall Mansion and Gilded Age Museum
- Goose Pond Reservation
- Smith College Botanic Garden
- Berkshire Museum
- Colonial Theater
- Don Muller Gallery