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Hotels in Middlefield

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Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
  • 4 min drive from Skyline Trail
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! (917 reviews)
Property has an old time roadside motel feel but updated to feel modern and spacious

Reviewed on Apr 27, 2026

Berkshires Untold
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
  • 8 min drive from Skyline Trail
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! (917 reviews)
Great location and resort. Very happy with accommodation's

Reviewed on Apr 27, 2026

Berkshire Mountain Lodge
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
  • 33 min drive from Skyline Trail
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! (2,340 reviews)
A+ for everything and the only annoying thing at times was the card used to enter the room.

Reviewed on Apr 26, 2026

Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
  • 14 min drive from Skyline Trail
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
The Red Lion Inn
The Ellery

The Ellery

3.5 out of 5
259 Elm Street Northampton MA
  • 8 min drive from Skyline Trail
Stay at this hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (1,003 reviews)
Such a sweet spot, so glad we were able to get a reservation. Wish we'd been hungrier and didn't have breakfast plans , but we did check out the offerings and they were lovely. And the community space was perfect as well, and the opportunity to grab a coffee, tea, cookie, yogurt etc at any hour was ...

Reviewed on Apr 27, 2026

The Ellery
River Valley Inn

River Valley Inn

2 out of 5
20 West St West Hatfield MA
  • 25 min walk from Skyline Trail
Stay at this motel in West Hatfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Pioneer Valley Indoor Karting and Connecticut ...
8.6/10 Excellent! (137 reviews)
Only negative thing was the shower drain. It was a little slow and the water was backed up a bit. But all in all, my stay was great.

Reviewed on Apr 25, 2026

River Valley Inn
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
  • 16 min drive from Skyline Trail
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in ...
9/10 Wonderful! (885 reviews)
Love it here! Definitely coming back!

Reviewed on Apr 24, 2026

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
  • 8 min drive from Skyline Trail
Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
9/10 Wonderful! (1,001 reviews)
the place is beautiful and serene. The room is clean and they have all the amenities that you need. Room temperature is perfect.

Reviewed on Apr 14, 2026

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd Lenox MA
  • 6 min drive from Skyline Trail
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 helpful staff ...
9.2/10 Wonderful! (1,001 reviews)
Room was very clean, staff helpful, coffee bar out of cream, the parking lot was in a disarray due to construction. The worse part was the driveway up to the hotel, it was full of huge potholes

Reviewed on Apr 25, 2026

Hampton Inn & Suites Berkshires-Lenox
Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst

2.5 out of 5
117 Conz St Northampton MA
  • 10 min drive from Skyline Trail
Book a stay at this business-friendly hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (1,006 reviews)
Room not clean, run down, Tony at front desk fantastic but we only stayed one night and then left …. Kind of disappointing I had to say

Reviewed on Apr 27, 2026

Quality Inn & Suites Northampton - Amherst
Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst

3 out of 5
115A Conz Street Northampton MA
  • 10 min drive from Skyline Trail
Book a stay at this business-friendly hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,001 reviews)
Very clean and quiet… Put us with our friends, which was awesome!

Reviewed on Apr 26, 2026

Fairfield Inn & Suites Springfield Northampton/Amherst
Hotel Northampton

Hotel Northampton

3.5 out of 5
36 King Street Northampton MA
  • 9 min drive from Skyline Trail
Book a stay at this historic hotel in Northampton. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (1,003 reviews)
Very Friendly and welcoming staff. Even the area was very relaxing especially being next to the Main Street. Beds are super comfortable. Highly recommend. Everything is within walking distance.

Reviewed on Apr 24, 2026

Hotel Northampton
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.

Find cheap hotels in Middlefield

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