Chester, MA
Travel Guide
Visit Chester

Red Roof Inn PLUS+ West Springfield
1254 Riverdale Street, West Springfield, MA
$94 nightly
The price is $107 total per night from Jul 6 to Jul 7
$107 total
Jul 6 - Jul 7
Total includes 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 (1,001 reviews)
"It’s was dog friendly"
Reviewed on Jun 22, 2025

D. Hotel Suites & Spa
1 Country Club Rd, Holyoke, MA
$150 nightly
The price is $168 total per night from Jun 29 to Jun 30
$168 total
Jun 29 - Jun 30
Total includes taxes and fees
Stay at this 3-star 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! (2,269 reviews)
"We stay here often, it never disappoints! Clean and friendly every time."
Reviewed on Jun 23, 2025

Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
$107 nightly
The price is $123 total per night from Jul 3 to Jul 4
$123 total
Jul 3 - Jul 4
Total includes 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! (1,000 reviews)
"The check in were hassel free, location parking all good. What I didn't like was it surpose to be a smoke free, but the hallway were smiling of marijuana occasionally."
Reviewed on Jun 26, 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! (121 reviews)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
Reviewed on May 14, 2025

Deluxe Queen Room with 2 Queen Beds
Lee
Stay at this vacation home in Lee. Enjoy laundry facilities, cable/satellite TV service, and air conditioning. Popular attractions Tanglewood Music Center and ...
No one there
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 ..."
Reviewed on May 5, 2025

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield
Stay at this cabin in Sandisfield. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Otis Ridge and Old Baldy Wildlife Sanctuary are ...
9.6/10 Exceptional! (38 reviews)
Bird watchers dream!
"Such a cozy cabin in the woods! We brought our own bird feeders and food and the birds came in immediately. We really enjoyed the peace and tranquillity. The cabin had a lovely porch with a patio table and chairs and we enjoyed our morning coffee listening to birdsong"
Reviewed on May 28, 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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