Chester, MA
Travel Guide
Visit Chester
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
$113 nightly
The price is $126 total per night from Sep 28 to Sep 29
$126 total
Sep 28 - Sep 29
Total with taxes and fees
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (656 reviews)
"Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again."
Reviewed on Sep 25, 2025
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street, Springfield, MA
$120 nightly
The price is $136 total per night from Sep 29 to Sep 30
$136 total
Sep 29 - Sep 30
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! (1,288 reviews)
"Close to the big e and the staff was good. Bartender Kim was a delight. Room was clean and spacious"
Reviewed on Sep 25, 2025
Red Roof Inn PLUS+ West Springfield
1254 Riverdale Street, West Springfield, MA
$89 nightly
The price is $102 total per night from Oct 5 to Oct 6
$102 total
Oct 5 - Oct 6
Total with taxes and fees
Stay at this hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (1,018 reviews)
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Reviewed on Sep 22, 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 3-star 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! (130 reviews)
Nice experience!
"The overall experience was great! Nice property. Ducks and geese were fun to watch off of our room’s deck."
Reviewed on Sep 21, 2025
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Becket
Stay at this cabin in Becket. Enjoy a garden, laundry facilities, and furnished lanais. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
9.6/10 Exceptional! (191 reviews)
"We appreciated how clean and well stocked the cottage was. The owner was very easy to work with. Accurate description of a quiet, secluded get-away in the woods"
Reviewed on Sep 1, 2025
Spacious 5-bedroom house in charming Lee with WiFi
Lee
Stay at this vacation home in Lee. Enjoy laundry facilities and in-room fireplaces. Popular attractions Tanglewood Music Center and Berkshire Mountain Country ...
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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- Big E
- Tanglewood Music Center
- Eastern States Exposition
- Smith College
- National Shrine of the Divine Mercy
- Mount Holyoke College
- Norman Rockwell Museum
- Ski Butternut
- Connecticut River
- Holyoke Mall
- Lee Premium Outlets
- Jacob's Pillow
- The Mount
- Bousquet Ski Area
- Naumkeag Museum
- Olympia Ice Center
- Ventfort Hall Mansion and Gilded Age Museum
- Berkshire Botanical Garden
- Historic Northampton
- Berkshire Museum
- Otis Reservoir
- Shakespeare and Company
- Berkshire Mountain Country Store
- Smith College Botanic Garden
- Goose Pond Reservation
- Colonial Theater
