Search for Cheap Deals on
Kid-Friendly Hotels in The Berkshires

Check Last Minute The Berkshires Hotel Deals

Tonight Sep 28 - Sep 29Next weekend Oct 4 - Oct 6

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking, and you save up to 60%!

Featured The Berkshires Family Hotels

Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a health club, and in-room massages. Our guests praise the helpful staff in our ...
Vacation Village in the Berkshires
Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
Stay at this hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our ...
Hotel Downstreet
Stay Berkshires
Stay Berkshires
2 out of 5
1146 Cold Spring Road, Williamstown, MA
Stay at this hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Sterling and Francine Clark Art Institute and The ...
Stay Berkshires
Williamstown Motel
Williamstown Motel
2 out of 5
295 Main Street, Route 2, Williamstown, MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly motel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Williamstown Motel
Cozy Corner Motel
Cozy Corner Motel
2 out of 5
284 Sand Springs Rd. Rte 7, Williamstown, MA
Fully refundableReserve now, pay when you stay
Book a stay at this family-friendly motel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Cozy Corner Motel
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
2 out of 5
980 Pleasant Street, Lee, MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly motel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Econo Lodge Lee - Great Barrington
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3 out of 5
37 Corey Rd, Hancock, MA
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 bars/lounges. Our guests praise the property condition in our reviews. Popular ...
Jiminy Peak Mountain Resort
Lantern House Motel
Lantern House Motel
2.5 out of 5
256 Stockbridge Road, Great Barrington, MA
Stay at this motel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Housatonic River and Lake Mansfield Park are located ...
Lantern House Motel
Hotel On North
Hotel On North
3.5 out of 5
297 North Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
Hotel On North
Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge
2 out of 5
42 Stockbridge Rd, West Stockbridge, MA
Stay at this motel in West Stockbridge. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions ...
Pleasant Valley Motel West Stockbridge
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox
2.5 out of 5
445 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
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 ...
Hampton Inn & Suites Berkshires-Lenox
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
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 ...
The Yankee, Trademark Collection by Wyndham
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.

Hotels with Pools 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
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! (1,000 reviews)
"Reasonable, convenient, clean, includes breakfast."

Reviewed on Sep 23, 2024

The Yankee, Trademark Collection by Wyndham
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a health club, and in-room massages. Our guests praise the helpful staff in our ...
8.6/10 Excellent! (1,712 reviews)
"We enjoyed our stay at Vacation Villa and the condo was extremely spacious and comfortable. The only complaint is the very soft bed. Upon check- in we were told we were 15 minutes early and had to stand in another line to wait to get a different room that would be ready at 3:45. Since we are gold ..."

Reviewed on Sep 22, 2024

Vacation Village in the Berkshires
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3 out of 5
One West Street, Pittsfield, MA
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (649 reviews)
"We had a great stay. Out in room refrigerator was t working but after calling the front desk, it was quickly replaced. Shower head placement was a bit unusual but after the first night of limited hot water, it was back to hot the rest of our stay. Towels were replaced frequently. Beds were comfortable. ..."

Reviewed on Sep 21, 2024

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
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.

Hotels With Connecting Rooms in The Berkshires

The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
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 ...
The Black Swan Lee - Lenox, Ascend Hotel Collection
Chestnut Lodge
Chestnut Lodge
3.5 out of 5
75 Chestnut Street, Lee, MA
Stay at this 3.5-star guesthouse in Lee. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Goose Pond Reservation and Lee Premium Outlets ...
Chestnut Lodge
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3 out of 5
One West Street, Pittsfield, MA
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
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.

Cheap Family Hotels in The Berkshires

When you’ve got the whole crew on the The Berkshires travel itinerary, you’re probably looking for a hotel that’s a little different than when you’re on a vacay with pals. Luckily, planning your last-minute getaway can be easy—you can score some of the best The Berkshires hotels for families when you book a Hotwire Hot Rate hotel deal.

On the Family (Vacation) Plan

Traveling with the entire bunch can get costly, but you can keep your budget intact (and a smile on everyone’s face) when you book a giant-size Hotwire Hot Rate deal on your stay in a family hotel in The Berkshires. And get ready to have a rousing round of high-fives from the kids, because these spots are a total hole-in-one for fun.

Just Kidding

Imagine you and the rest of the family in one of the best kid friendly hotels in The Berkshires. Sure, the kids are loving it—maybe they aren’t even arguing—you can dream, anyway. Great times are being had by everyone, thanks to you booking the family hotel in The Berkshires of your dreams, with every amenity you’re looking for, and for way less than you expected. There’s even some cash left for ice creams all around. With sprinkles.

Frequently Asked Questions About Family Hotels

How to get last-minute deals on family hotels in The Berkshires?

Looking for the very best last-minute deals on family friendly hotels in The Berkshires? You may think you’ve got your work cut out for you, but booking a Hotwire Hot Rate hotel deal will get you a top-tier place for way less than you expect, even if you’re short on time. In fact, you could save up to 60% on cheap family hotels in The Berkshires versus booking a listed rate two weeks earlier—we’re talking hotels as low as $70 kind of deals. Looks like that ice cream budget just got upgraded.

Where should a family stay in The Berkshires?

There are a lot of great places to stay in The Berkshires, and with 999 hotels to choose from, you’ll have some prime options ready for the picking. If you (and the kids) have your heart set on one of the best family hotels in The Berkshires, you don’t have to break the bank—you can get a super-sweet 4-star hotel for a 2-star price when you book a Hotwire Hot Rate hotel deal and keep your cash for the upcoming family fun.

How can I find kid friendly hotels in The Berkshires?

Booking kid friendly hotels in The Berkshires is a breeze with Hotwire. You can narrow down your options by selecting the area of The Berkshires that you want to stay in, which amenities the fam just has to have, and even by the reviews. If you book a Hotwire Hot Rate hotel deal, you won’t know the exact place where you’ll be staying until you’ve reserved, but you can make sure it checks all the boxes for your perfect spot.

Is it safe to travel to The Berkshires during the coronavirus (COVID-19) crisis?

With the most recent COVID-19 closures and reopenings, you’re probably wondering is it safe to travel to The Berkshires right now. When you book your last-minute getaway to The Berkshires, be sure to check the most up-to-date info on safety measures, closures, and important guidance on traveling during the coronavirus.