Name: Vacation Village in the Berkshires
Price range: $152 total
Rating: 8.8

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

$167 nightly

$186 total

Jul 2 - Jul 3

Total with taxes and fees

Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

8.8/10 Excellent! (1,008 reviews)

"No real breakfast"

Reviewed on Jun 21, 2026

The Yankee Inn

461 Pittsfield Rd Lenox MA

$140 nightly

$156 total

Jun 24 - Jun 25

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

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

$136 nightly

$152 total

Jun 24 - Jun 25

Total with taxes and fees

Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...

8.8/10 Excellent! (2,408 reviews)

"very scenic and well maintained property"

Reviewed on Jun 23, 2026

See all 980 properties in Cheshire

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.

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...

8.8/10 Excellent! (2,408 reviews)

"very scenic and well maintained property"

Reviewed on Jun 23, 2026

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Whitingham VT

Stay at this apartment in Whitingham. Enjoy free breakfast, a sauna, and laundry facilities. Popular attractions Harriman Reservoir and Readsboro Community Library ...

9.8/10 Exceptional! (6 reviews)

"We had a wonderful Memorial Day weekend here with our two young daughters. We enjoyed the gorgeous views, the hot tub, and the very comfortable beds. There was plenty of space for four people. Chris responded very quickly to any questions we had. A very unique home that we are happy to have made ..."

Reviewed on May 25, 2026

Huttopia Berkshires

312 Kittle Rd Williamstown MA

Stay at this campground in Williamstown. Enjoy free parking, breakfast (surcharge), and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ...

9.4/10 Exceptional! (10 reviews)

"Excelente servicio"

Reviewed on Mar 8, 2026

See all properties in Cheshire

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

St Mary's of the Assumption Church

5/5(1 review)

St Mary's of the Assumption Church is just one of the places to see in Cheshire, so why not enjoy the other things to explore during your travels? Discover the area's mountain views, or seek out its ski slopes.