Chester Travel Guide
Tourist Guide
Visit Chester
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
The price is AU$202 per night from 12 Jan to 13 Jan
AU$202
12 Jan - 13 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! (2,261 reviews)
The staff was super helpful and courteous. The room and public areas were superb. We did not use the pool but the area was neatly kept and very attractive (brightly colored and well lit). The hotel is located in a safe area, surrounded by woods, and overlooking the Connecticut River.
Reviewed on 6 Jan 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is AU$198 per night from 1 Feb to 2 Feb
AU$198
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! (807 reviews)
I've stayed here several times over the past two years. A real gem of a location, especially if you are staying several nights.
Reviewed on 5 Jan 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
The price is AU$164 per night from 23 Jan to 24 Jan
AU$164
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! (1,001 reviews)
Another good 2 night stay. Did have a slow shower drain but reported that to maintenance and it was fixed right away. Good service. And also the restaurant is quite good featuring an American menu with a Southern emphasis. The parking garage demo is moving quickly by the way. More parking close to ...
Reviewed on 7 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
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! (6 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
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Great Barrington MA
Stay at this holiday home in Great Barrington. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Ski Butternut and Lake Buel are located ...
10/10 Exceptional! (28 reviews)
The house was clean and huge…. Lots of room for many people and activities!
Reviewed on 27 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.
