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Hotels in Middlefield

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Choose from 1058 Middlefield Hotel Deals

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 ...
8.6/10 Excellent! (2,179 reviews)
My stay was great with no problems.

Reviewed on Dec 19, 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
  • 7 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 pool in our ...
9/10 Wonderful! (1,006 reviews)
The room is so spotless, bathroom is so luxurious! The bed is so soft and sleep very quickly! The staffs are so great! Quick to answer to my questions and my needs. Definitely come back again to stay!

Reviewed on Dec 22, 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
  • 14 min drive from Skyline Trail
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! (993 reviews)
N/a

Reviewed on Dec 20, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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! (793 reviews)
Spacious room and loved pool and hot tub!

Reviewed on Dec 19, 2025

Berkshire Mountain Lodge
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. ...
8.6/10 Excellent! (1,002 reviews)
I had always wanted to stay at The Red Lion Inn and decided to treat myself to a one-night stay. Since it was in December I was especially excited to have a fireplace in the room. Sadly, I learned the fireplace didn’t work and that they are renovating some of the systems, but offered no partial refund ...

Reviewed on Dec 23, 2025

The Red Lion Inn
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! (817 reviews)
Room was very nice and spacious!

Reviewed on Dec 14, 2025

Berkshires Untold
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! (806 reviews)
very good stay my only recommendation would be to have more coffee supplies as their is only enough for one pot of coffee and we were staying two days other than that very peaceful and comfortable.

Reviewed on Dec 22, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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 ...
9/10 Wonderful! (1,000 reviews)
Great, gracious hotel with old time charm. Clean and comfortable too.

Reviewed on Dec 20, 2025

Hotel Northampton
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 ...
9/10 Wonderful! (926 reviews)
Stayed here to help daughter move out at Smith. Super convenient to the school and nice to have breakfast/coffee in the mornings. Was able to check in early which was a BIG bonus after taking a red-eye from the west coast. Much appreciated!

Reviewed on Dec 18, 2025

The Ellery
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd Great Barrington MA
  • 26 min drive from Skyline Trail
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
8.8/10 Excellent! (710 reviews)
The room was super clean and comfortable. Nice television and great bathroom. Highly recommend!

Reviewed on Dec 21, 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield

2.5 out of 5
2 Southampton Rd Westfield MA
  • 38 min drive from Skyline Trail
Book a stay at this business-friendly hotel in Westfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (902 reviews)
Stayed one night had no problems

Reviewed on Nov 30, 2025

Quality Inn Westfield - Springfield
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St Pittsfield MA
  • 12 min drive from Skyline Trail
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,001 reviews)
Very friendly and good Breakfast.

Reviewed on Dec 14, 2025

Best Western Plus Berkshire Hills Inn & Suites
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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