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Top The Berkshires Family-Friendly Hotels

Our top choices for The Berkshires family-friendly hotels

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (23)
"Brand new hotel. Really nice staff. Great location to Tanglewood and great rates. "
The price is 3.562.284 ₫
3.979.072 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (732)
"We had a nice stay at the Fairfield Inn in Great Barrington. It’s conveniently located not far from downtown and just a short drive to Stockbridge. The front desk staff was welcoming, the room spacious and clean, and plenty of breakfast items to choose from. Definitely recommend!"
The price is 3.769.194 ₫
4.210.189 ₫ total
includes taxes & fees
10 Sept - 11 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is 3.338.241 ₫
3.728.815 ₫ total
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (865)
"Consistently a clean room with welcoming staff."
The price is 2.873.022 ₫
3.209.165 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1002)
"Very clean rooms and excellent staff."
The price is 2.800.274 ₫
3.127.906 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Berkshire Hills Inn & Suites

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (967)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is 4.190.922 ₫
4.681.260 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Jiminy Peak Mountain Resort

Simsbury Inn

3.5 star property
9.2 out of 10, Wonderful, (266)
"Lovely property Everyone kind and gracious. "
The price is 6.035.982 ₫
7.517.301 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Simsbury Inn

Quality Inn Westfield - Springfield

2.5 star property
7.2 out of 10, Good, (829)
"An affordable and comfortable stay. Very friendly staff as well. "
The price is 2.666.112 ₫
2.978.047 ₫ total
includes taxes & fees
8 Sept - 9 Sept
Quality Inn Westfield - Springfield

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (61)
"Oguz, the manager treated us like family. It was a very pleasant and relaxing stay."
Deerfield Valley Inn

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.6 out of 10, Good, (545)
"Excellent location, friendly service, clean, comfortable room."
The price is 1.976.850 ₫
2.208.273 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Travelodge by Wyndham Great Barrington Berkshires
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.

Family-friendly hotels with free breakfast in The Berkshires

Family-friendly hotels with pools in The Berkshires

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.

Top The Berkshires Hotel Reviews