Chester
Travel Guide
Visit Chester
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
The price is €124 per night from 13 Apr to 14 Apr
€124
13 Apr - 14 Apr
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 ...
9.4/10 Exceptional! (2,217 reviews)
Breakfast had good variety of choices. Staff were friendly and responsive. Hot tub and pool area was filled with adults and children the two time we considered going so not able to take advantage of that amenity.
Reviewed on 27 Mar 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is €103 per night from 27 Apr to 28 Apr
€103
27 Apr - 28 Apr
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! (888 reviews)
very clean and friendly staff
Reviewed on 24 Mar 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
The price is €68 per night from 31 Mar to 1 Apr
€68
31 Mar - 1 Apr
includes taxes & fees
Stay at this lodge in Lenox. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in their reviews. ...
9/10 Wonderful! (882 reviews)
I spent 2 lovely nights here on my way through the Berkshires. Everyone was so kind, helpful and professional. Flatbread was delicious and a cup of tea in the cozy fire nook was perfect.
Reviewed on 28 Mar 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 Tanglewood Music Center and The Mount are located ...
8.6/10 Excellent! (141 reviews)
I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. ...
Reviewed on 9 Feb 2026
Peace and quiet on the lake
Becket MA
Stay at this holiday home in Becket. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
9.6/10 Exceptional! (234 reviews)
Host was great! Quick communication. Place is a gem for peace and tranquility! The home is beautiful with great view.
Reviewed on 18 Feb 2026
Family Ski Getaway in the Berkshires
Great Barrington MA
Stay at this holiday home in Great Barrington. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Monument Mountain Reservation and Art et ...
9/10 Wonderful! (12 reviews)
Loved our time here. It was a very cozy set up for a snowy week away, with a pellet stove, an ample amount of puzzles stocked in the house, and the surprise perk of Studley, a 12 year old cuddle machine of a cat who lives here and provided great company. The host was very responsive to all of my ...
Reviewed on 4 Mar 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.
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.
