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
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is SAR 363 per night from Apr 16 to Apr 17
SAR 363
SAR 406 total
includes taxes & fees
16 Apr - 17 Apr
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (539 reviews)
"Enjoyed having an excellent meal and bar was very convenient."

Reviewed on 30 March 2025

Life House 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 SAR 332 per night from Apr 10 to Apr 11
SAR 332
SAR 370 total
includes taxes & fees
10 Apr - 11 Apr
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! (1,003 reviews)
Great but firm mattress
"Great location and the room was very nice. The only issue I had was the bed was very firm."

Reviewed on 2 April 2025

The Yankee, Trademark Collection by Wyndham
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
The price is SAR 446 per night from Apr 8 to Apr 9
SAR 446
SAR 551 total
includes taxes & fees
8 Apr - 9 Apr
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
8.8/10 Excellent! (615 reviews)
"Clean and great location"

Reviewed on 28 March 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
See all 1,043 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
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in ...
8.6/10 Excellent! (1,792 reviews)
"The location to jimney peak was great."

Reviewed on 26 March 2025

Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3 out of 5
37 Corey Rd, Hancock, MA
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 bars/lounges. Our guests praise the property condition in our reviews. Popular ...
8.2/10 Very Good! (925 reviews)
"Staff was exceptionally helpful and friendly."

Reviewed on 14 January 2025

Jiminy Peak Mountain Resort
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
Lanesborough
Stay at this vacation home in Lanesborough. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Jiminy Peak Mountain Resort and Crane ...
9.6/10 Exceptional! (241 reviews)
Quaint Carriage House
"This beautiful carriage house is ingeniously designed with no wasted space. Surrounded by nature, it is totally private, yet it is two minutes from shops and restaurants. The window seats are sublime and the heated floors offered relief after afternoons spent hiking in the cold."

Reviewed on 12 March 2025

Berkshire Village Carriage House - Super Private!!
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