Name: Berkshires Untold
Price range: $87 total
Rating: 9

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

$134 nightly

$149 total

Mar 25 - Mar 26

Total with taxes and fees

Book a 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 our reviews. ...

9.4/10 Exceptional! (2,218 reviews)

The pool is great if you are travelling with kids like us

Reviewed on Mar 22, 2026

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

$108 nightly

$120 total

Apr 21 - Apr 22

Total with taxes and fees

Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...

9/10 Wonderful! (884 reviews)

This is our 3rd year staying here for my son’s birthday in March. Affordable and having the 2 rooms with a kitchen is so nice. My son’s favorite part is the pool which is always warm and clean, never smells too strong like some places. Hot tub feels amazing too. Will be back next year, or sooner ...

Reviewed on Mar 22, 2026

Berkshires Untold

194 Pittsfield Rd Lenox MA

$78 nightly

$87 total

Mar 29 - Mar 30

Total with taxes and fees

Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...

9/10 Wonderful! (880 reviews)

Wonderful place, great toiletries and great friendly staff. We will be back

Reviewed on Mar 22, 2026

See all 872 properties in Chester

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 WiFi, free parking, and a fitness center. 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 Feb 9, 2026

Peace and quiet on the lake

Becket MA

Stay at this vacation home in Becket. Enjoy free WiFi, 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 Feb 18, 2026

Family Ski Getaway in the Berkshires

Great Barrington MA

Stay at this vacation home in Great Barrington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Monument Mountain Reservation and Art ...

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 Mar 4, 2026

See all properties in Chester

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.