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 16 to Nov 17
$125 total
Nov 16 - Nov 17
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! (1,291 reviews)
All of the ladies at the desk both for check in and check out were very friendly, nice and courteous!! Breakfast buffet was good, hot food could of been warmer( home fries and eggs) plenty of other choices though. The room was clean and comfortable. The pool was nice, not enough of pool towels ...
Reviewed on Nov 7, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
$113 nightly
The price is $126 total per night from Nov 11 to Nov 12
$126 total
Nov 11 - Nov 12
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 ...
9/10 Wonderful! (750 reviews)
Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome.
Reviewed on Nov 4, 2025
Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
$85 nightly
The price is $97 total per night from Dec 7 to Dec 8
$97 total
Dec 7 - Dec 8
Total with taxes and fees
Book a stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7/10 Good! (1,004 reviews)
The owner makes me feel like I am a personal friend of his and the best part of his day is when I walk in the door.
Reviewed on Nov 7, 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! (132 reviews)
All as promised!
Reviewed on Oct 21, 2025
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
Great Barrington, MA
Stay at this vacation home in Great Barrington. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Monument Mountain Reservation ...
9/10 Wonderful! (2 reviews)
Great location with nice space to hangout as a group - appreciated the music and games options. Comfortable space. Host was very responsive and checked in with us. Small bathroom for 4 people but nice big windows throughout the house for good light and great views. Everything was clean and ready ...
Reviewed on Oct 27, 2025
The Kemble- Built by a US Secretary of State in Lenox
Lenox
Book a stay at this family-friendly villa in Lenox. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Tanglewood Music Center and ...
9.8/10 Exceptional! (17 reviews)
Perfect Wedding Venue
We booked this house as the venue for our wedding, and it was absolutely perfect! Every room was gorgeous, with elegant décor and plenty of space for our guests. Even the bathrooms were stunning, making every part of the home feel special. The kitchen had everything we needed to host our 50-person ...
Reviewed on Mar 30, 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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- Big E
- Tanglewood Music Center
- Eastern States Exposition
- Smith College
- National Shrine of the Divine Mercy
- Ski Butternut
- Mount Holyoke College
- Connecticut River
- Lee Premium Outlets
- Norman Rockwell Museum
- Jacob's Pillow
- The Mount
- Holyoke Mall
- Bousquet Ski Area
- Naumkeag Museum
- Olympia Ice Center
- Ventfort Hall Mansion and Gilded Age Museum
- Berkshire Botanical Garden
- Historic Northampton
- Otis Reservoir
- Shakespeare and Company
- Smith College Botanic Garden
- Berkshire Mountain Country Store
- Colonial Theater
- Chicopee Falls Dam
- Mountain Park
- Goose Pond Reservation
