Family friendly Hotels in The Berkshires, Massachusetts

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Check availability on The Berkshires Family friendly Hotels

Top The Berkshires Family friendly Hotels

Our top choices for The Berkshires family-friendly hotels

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1009)
"The staff and location make it excellent"
The price is P7,015
P7,836 total
includes taxes & fees
Sep 24 - Sep 25
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby sitting area

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (39)
"Hotel was clean, the rooms had good space, the breakfast was excellent and the team there was very friendly and accommodating "
The price is P7,208
P8,052 total
includes taxes & fees
Sep 21 - Sep 22
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Property amenity

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (735)
"Was the perfect stop over for our way home. All the employees were extremely friendly. "
The price is P9,049
P10,108 total
includes taxes & fees
Sep 22 - Sep 23
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (877)
"Our stay was very pleasant "
The price is P6,204
P6,930 total
includes taxes & fees
Sep 21 - Sep 22
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1006)
"Very clean rooms and excellent staff."
The price is P6,047
P6,754 total
includes taxes & fees
Sep 21 - Sep 22
Best Western Plus Berkshire Hills Inn & Suites
Jiminy Peak Mountain Resort
Skiing

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (975)
"Staff was very nice and helpful. Property was a little bit outdated but very clean and functional. Surroundings are beautiful!!"
The price is P9,049
P10,108 total
includes taxes & fees
Sep 21 - Sep 22
Jiminy Peak Mountain Resort
Quality Inn Westfield - Springfield
Lobby

Quality Inn Westfield - Springfield

2.5 star property
7.2 out of 10, Good, (844)
"Was centrally located and the room was immaculate Thank you for an amazing stay "
The price is P5,563
P6,214 total
includes taxes & fees
Oct 5 - Oct 6
Quality Inn Westfield - Springfield
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"We had a lovely time staying here. "
Deerfield Valley Inn
Simsbury Inn
Exterior

Simsbury Inn

3.5 star property
9.2 out of 10, Wonderful, (268)
"The staff was wonderful and very accommodating. I had a very nice dinner and the enjoyed the experience . I’ll definitely stay here again."
The price is P16,448
P20,159 total
includes taxes & fees
Sep 21 - Sep 22
Simsbury Inn
Travelodge by Wyndham Great Barrington Berkshires
In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.6 out of 10, Good, (547)
"Excellent location, friendly service, clean, comfortable room."
The price is P4,269
P4,768 total
includes taxes & fees
Sep 21 - Sep 22
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.
View all properties

Top The Berkshires Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"We come here regularly. We are satisfied with its price and location."
Andrew 1-night trip
Posted 15 hours ago
Hotel Downstreet, an Ascend Collection Hotel

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