Chester
Travel Guide
Visit Chester
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
The price is HK$933 per night from 22 Jan to 23 Jan
HK$933
HK$1,084 total
22 Jan - 23 Jan
includes taxes & fees
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 their reviews. Popular ...
9.2/10 Wonderful! (2,226 reviews)
Was just there for a short overnight stay but room was comfortable clean, fixtures in good shape, service front desk was professional.
Reviewed on 17 Jan 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is HK$769 per night from 1 Feb to 2 Feb
HK$769
HK$1,034 total
1 Feb - 2 Feb
includes taxes & fees
Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ...
9/10 Wonderful! (814 reviews)
There needs to be an adult only hot tub. Both days we used, other kids had it taken over.
Reviewed on 18 Jan 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
The price is HK$764 per night from 23 Jan to 24 Jan
HK$764
HK$853 total
23 Jan - 24 Jan
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,006 reviews)
generally good
Reviewed on 19 Jan 2026
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 Wi-Fi, free parking and a fitness centre. Popular attractions The Mount and Wyndhurst Golf & Club are located ...
8.4/10 Very Good! (139 reviews)
Condo was a great space. Bathroom walls should be repainted as stains are evident. There were also stains on the couch which I cleaned.
Reviewed on 3 Jan 2026
Pet Friendly Riverfront Home in Great Barrington
Great Barrington MA
Stay at this holiday home in Great Barrington. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Monument Mountain Reservation and Art et ...
9.2/10 Wonderful! (7 reviews)
Marisa's place was cozy and well-decorated. We enjoyed staying there for New Years and it was a good distance to the local downtowns while being quietly tucked away by the river.It was unclear to our party that the outdoor cats on the property lived within the rental unit until we received our check-in ...
Reviewed on 5 Jan 2026
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Lanesborough MA
Stay at this holiday home in Lanesborough. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ...
10/10 Exceptional! (8 reviews)
Beautiful lake house, isolated enough that you're not in the city, but close access to amenities and good food. The hot tub was an absolutely amazing experience, and Adam was thoughtful with providing instructions on how to use the firepit and outdoor heating as well. Would love to stay here ...
Reviewed on 4 Dec 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 on your trip to Chester. Wander the lakeside and forests in this relaxing area.
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