Deals on vacations and trips to Chester
Save when you book Chester package deals
Top Chester hotels deals
D. Hotel Suites & Spa
1 Country Club Rd, Holyoke, MA
Free Cancellation
$134 nightly
The price is $150 total per night
$150 total
Jun 8 - Jun 9
Total includes taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. You'll appreciate the gym, bar/lounge, and laundry facilities.
Pool
Hot Tub
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street, Springfield, MA
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $129 total per night
$129 total
Jun 1 - Jun 2
Total includes taxes and fees
This hotel features an indoor pool and a gym. Families will appreciate the arcade/game room and onsite laundry facilities. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking.
Pool
Breakfast included
Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $96 total per night
$96 total
Jun 15 - Jun 16
Total includes taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $189 total per night
$189 total
Jun 11 - Jun 12
Total includes taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. Express check-in is provided and the front desk is staffed around-the-clock.
Pet friendly
Parking included
The Ellery
259 Elm Street, Northampton, MA
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $166 total per night
$166 total
Jun 11 - Jun 12
Total includes taxes and fees
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning. A garden, a lobby fireplace, and a picnic area are also on offer.
Breakfast included
Pet friendly
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$129 nightly
The price is $144 total per night
$144 total
Jun 2 - Jun 3
Total includes taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
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.
Photos of local treasures
Browse Chester vacation photos for more inspiration
