Chester, MA
Travel Guide
Visit Chester
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
$121 nightly
The price is $135 total per night from Mar 8 to Mar 9
$135 total
Mar 8 - Mar 9
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! (2,215 reviews)
We received a warm welcome Waited just a few minutes for room to be ready Breakfast included with stay which is always a plus to get you on your way Enough parking for all
Reviewed on Mar 2, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$121 nightly
The price is $136 total per night from Apr 2 to Apr 3
$136 total
Apr 2 - Apr 3
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! (866 reviews)
Love it here. We stay a few times a year and are actually local to the hotel. Just a relaxed experience.
Reviewed on Mar 1, 2026
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
$93 nightly
The price is $103 total per night from Mar 11 to Mar 12
$103 total
Mar 11 - Mar 12
Total with taxes and fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9.2/10 Wonderful! (1,003 reviews)
Breakfast was delicious. Pool and hot tub were very clean. The rooms were nice for the price point.
Reviewed on Mar 2, 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 ...
8.6/10 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
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! (31 reviews)
Great house with plenty of bedrooms and space! Perfect location for a ski weekend.
Reviewed on Jan 16, 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
- Big E
- Norman Rockwell Museum
- Ski Butternut
- Eastern States Exposition
- Smith College
- Mount Holyoke College
- Holyoke Mall
- Bousquet Ski Area
- Connecticut River
- Jacob's Pillow
- The Mount
- Lee Premium Outlets
- Naumkeag Museum
- Historic Northampton
- Olympia Ice Center
- Smith College Botanic Garden
- Berkshire Museum
- Lenox Library
- Ventfort Hall Mansion and Gilded Age Museum
- Wyndhurst Golf & Club
- Berkshire Botanical Garden
- Berkshire Mountain Country Store
- Shakespeare and Company
- Goose Pond Reservation
- Otis Ridge