Chester, MA
Travel Guide
Visit Chester
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street Springfield MA
$111 nightly
The price is $125 total per night from Nov 23 to Nov 24
$125 total
Nov 23 - Nov 24
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 ...
8/10 Very Good! (1,295 reviews)
Everything was good
Reviewed on Nov 18, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$120 nightly
The price is $135 total per night from Nov 30 to Dec 1
$135 total
Nov 30 - Dec 1
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! (758 reviews)
The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway
Reviewed on Nov 14, 2025
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
$134 nightly
The price is $150 total per night from Nov 23 to Nov 24
$150 total
Nov 23 - Nov 24
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! (2,251 reviews)
Courteous staff, clean room, free breakfast buffet.
Reviewed on Nov 17, 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.
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! (133 reviews)
All as promised!
Reviewed on Oct 21, 2025
Pet Friendly Riverfront Home in Great Barrington
Great Barrington MA
Stay at this vacation home in Great Barrington. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Monument Mountain Reservation and Art et ...
8.6/10 Excellent! (3 reviews)
Amazing cosy property. The berkshires are beautiful and Marisa was a great host. Thank you for having us!
Reviewed on Nov 9, 2025
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! (228 reviews)
Amazing house . Only stayed for a weekend but was very impressed how clean comfortable this place was. Beautiful yard with great fire pit . Nice doc to sit on. We actually went out on the kayak which was amazing. Did a lot of walking as well. Will definitely be back thank you Justin.
Reviewed on Nov 10, 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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- Big E
- National Shrine of the Divine Mercy
- Eastern States Exposition
- Smith College
- Mount Holyoke College
- Bousquet Ski Area
- Lee Premium Outlets
- Norman Rockwell Museum
- Holyoke Mall
- The Mount
- Connecticut River
- Jacob's Pillow
- Olympia Ice Center
- Historic Northampton
- Naumkeag Museum
- Smith College Botanic Garden
- Colonial Theater
- Berkshire Mountain Country Store
- Berkshire Botanical Garden
- Goose Pond Reservation
- Berkshire Museum
- Shakespeare and Company
- Lenox Library