Middlefield, MA

Travel Guide

Photo by Elizabeth Massa Peroulakis
Photo by Elizabeth Massa Peroulakis
Photo by Gregg Yutko
Photo by Gregg Yutko
Photo by Elizabeth Massa Peroulakis
Photo by Elizabeth Massa Peroulakis
Photo by Jason Weagle
Photo by Jason Weagle
Photo by Chris Addams
Photo by Chris Addams
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is AED 382 per night from Jan 4 to Jan 5
AED 382
AED 467 total
4 Jan - 5 January 2026
includes taxes & 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 ...
8.6/10 Excellent! (2,182 reviews)
A great place for our family to use as a base while skiing at Jiminy Peak! The pool was a huge hit.

Reviewed on 24 December 2025

Vacation Village in the Berkshires
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
The price is AED 372 per night from Jan 5 to Jan 6
AED 372
AED 415 total
5 Jan - 6 January 2026
includes taxes & 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 ...
9/10 Wonderful! (1,000 reviews)
The bed was very comfortable. The staff was helpful and courteous

Reviewed on 24 December 2025

The Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
The price is AED 324 per night from Jan 2 to Jan 3
AED 324
AED 362 total
2 Jan - 3 January 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (997 reviews)
While waiting for our vallet car due to construction. The hotel staff were engaging and had personal conversations with us. Rooms were good and all staff treated us exceptional. Give them an atta boy on proformance

Reviewed on 22 December 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 1,060 properties in Middlefield
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

Vacation Village in the Berkshires

3 out of 5
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 ...
8.6/10 Excellent! (2,182 reviews)
A great place for our family to use as a base while skiing at Jiminy Peak! The pool was a huge hit.

Reviewed on 24 December 2025

Vacation Village in the Berkshires
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
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 ...
10/10 Exceptional! (7 reviews)
Healthy food too!

Reviewed on 20 October 2025

Huttopia Berkshires
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7 Lenox MA
Stay at this condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions The Mount and Wyndhurst Golf & Club are located ...
8.4/10 Very Good! (137 reviews)
Great place

Reviewed on 23 December 2025

The Ponds at Foxhollow
See all properties in Middlefield
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

Skyline Trail

You can take time to visit Skyline Trail during your travels to Middlefield. Stroll along the area's lakeside, or simply savor its charming coffeehouses.

Skyline Trail