Chester, MA
Travel Guide
Visit Chester
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
$134 nightly
The price is $150 total per night from Aug 9 to Aug 10
$150 total
Aug 9 - Aug 10
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. ...
The Yankee Inn
461 Pittsfield Rd Lenox MA
$165 nightly
The price is $184 total per night from Aug 6 to Aug 7
$184 total
Aug 6 - Aug 7
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! (1,008 reviews)
"This was our fourth year in a row staying at the Inn. They have a new sitting area outside with a gas fire pit, very nice. The pool is always very well maintained. We like to stay in the older section room away from the main building, the beds are comfortable and the room is basic but clean and nice. ..."
Reviewed on Aug 5, 2026
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street Springfield MA
$119 nightly
The price is $135 total per night from Aug 9 to Aug 10
$135 total
Aug 9 - Aug 10
Total with taxes and fees
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 ...
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.
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
The Ponds at Foxhollow
3 Foxhollow Drive Route 7 Lenox MA
Stay at this aparthotel 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! (145 reviews)
"Quiet property. Convenient location."
Reviewed on Aug 2, 2026
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++
Lenox MA
Book a stay at this family-friendly vacation home in Lenox. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Tanglewood Music Center and ...
9.4/10 Exceptional! (65 reviews)
"Great stay, lots of space. A bit of an older house but lots of charm, and basically anything you need you can find here. Our stay was unfortunately rained out, but there was plenty of things to do in the house to keep us busy - pool table, TV, hot tub, games, large dining table that fit the six of ..."
Reviewed on May 27, 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.
Stay near popular Chester attractions
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- Tanglewood Music Center
- Big E
- Smith College
- National Shrine of the Divine Mercy
- Mount Holyoke College
- Eastern States Exposition
- Norman Rockwell Museum
- Lee Premium Outlets
- Holyoke Mall
- Connecticut River
- Jacob's Pillow
- Ski Butternut
- Olympia Ice Center
- The Mount
- Bousquet Ski Area
- Lenox Library
- Otis Reservoir
- Berkshire Botanical Garden
- Naumkeag Museum
- Smith College Botanic Garden
- Colonial Theater
- Wyndhurst Golf & Club
- Berkshire Mountain Country Store
- Ventfort Hall Mansion and Gilded Age Museum
- Shakespeare and Company
