Name: Berkshire Mountain Lodge
Price range: $181 total
Rating: 9

The Yankee Inn

461 Pittsfield Rd Lenox MA

$135 nightly

$150 total

Jul 9 - Jul 10

Total with taxes and fees

Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...

9.2/10 Wonderful! (1,005 reviews)

"I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here."

Reviewed on Jun 23, 2026

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

$132 nightly

$147 total

Jun 30 - Jul 1

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. ...

9.2/10 Wonderful! (2,155 reviews)

"Very nice place to stay. Nice pool and hot tub"

Reviewed on Jun 24, 2026

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

$162 nightly

$181 total

Jul 26 - Jul 27

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! (999 reviews)

"We thoroughly enjoyed our stay. The rooms are spacious and beautifully furnished, and having a stove and refrigerator along with a separate living/dining room was a definite plus. The 24/7 coffee and hot chocolate machine in the lobby was another perk, as were the hot tub and large (albeit shallow) ..."

Reviewed on Jun 24, 2026

See all 870 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 aparthotel in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and National Shrine of the ...

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

Cozy Riverside Berkshires Retreat

Great Barrington MA

Stay at this vacation home in Great Barrington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions National Shrine of the Divine Mercy and ...

9.4/10 Exceptional! (16 reviews)

"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."

Reviewed on Jun 13, 2026

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts

Cummington MA

Book a stay at this family-friendly lodge in Cummington. Enjoy a garden, mountain biking on site, and a pool table.

10/10 Exceptional! (3 reviews)

"Spiritual, artistic home. Wonderful."

Reviewed on Jun 10, 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.