Family Hotels & Resorts in The Berkshires

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Family Hotels

Tonight
7 Aug - 8 Aug
Tomorrow
8 Aug - 9 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Best The Berkshires Family Hotels

Holiday Inn Express & Suites Pittsfield - Berkshires
Enjoy a diverse selection of hot and cold dishes at our buffet.

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
9.6 out of 10, Exceptional, (11)
"Really enjoyed my stay here, definitely need a car to get around"
The price is AU$261
includes taxes & fees
18 Aug - 19 Aug
Holiday Inn Express & Suites Pittsfield - Berkshires
The Black Swan Lee - Lenox, Ascend Hotel Collection
Relax in a serene lakeside setting with Adirondack chairs and a tranquil atmosphere.

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Beautiful location!"
The price is AU$218
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Relax in a welcoming space with comfortable seating and a stunning chandelier.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (724)
"Was the perfect stop over for our way home. All the employees were extremely friendly. "
The price is AU$259
includes taxes & fees
25 Aug - 26 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Dine in style with a long table set for a memorable meal, surrounded by cushioned chairs and large windows offering a view of the outdoors.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (852)
"Consistently a clean room with welcoming staff."
The price is AU$198
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Best Western Plus Berkshire Hills Inn & Suites
Welcome to our reception area, featuring a comfortable seating area, a reception desk, and a beautiful abstract art piece.

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1004)
"Very nice stay"
The price is AU$204
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Berkshire Hills Inn & Suites
Simsbury Inn
Stroll through the serene garden, surrounded by lush greenery and a central fountain.

Simsbury Inn

3.5 star property
9.2 out of 10, Wonderful, (263)
"Excellent all around. Staff could not have been more helpful."
The price is AU$434
includes taxes & fees
26 Aug - 27 Aug
Simsbury Inn
Jiminy Peak Mountain Resort
Set amidst lush greenery, this hotel complex offers a serene escape with pathways connecting its various buildings.

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (958)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is AU$273
includes taxes & fees
1 Sept - 2 Sept
Jiminy Peak Mountain Resort
Quality Inn Westfield - Springfield
Relax in a stylish space with a seating area, wooden desk, and large windows offering a view of the outdoors.

Quality Inn Westfield - Springfield

2.5 star property
7.2 out of 10, Good, (826)
"The price was good for a clean room and nice breakfast."
The price is AU$168
includes taxes & fees
24 Aug - 25 Aug
Quality Inn Westfield - Springfield
Deerfield Valley Inn
Surrounded by snow-covered trees, this serene winter scene offers a peaceful retreat.

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (54)
"I liked that it was right on the scenic route"
Deerfield Valley Inn
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Enjoy a meal at John Harvard's Restaurant & Brewery, located near a pool area with lounge chairs.

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

9.8 out of 10, Exceptional, (18)
"The condo was clean and well located for easy access to the mountain. We were there for tri-state races and having easy acass to the mountain was exactly what we needed for a fun weekend. We would stay here again."
The price is AU$373
includes taxes & fees
13 Aug - 14 Aug
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Wonderful place to stay"
Adair 1-night trip
Posted 23 hours ago
The Yankee, Trademark Collection by Wyndham