Photo by Photo courtesy of Berkshire Visitors Bureau

Hotels with Childcare in The Berkshires, Massachusetts

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Check availability on The Berkshires Hotels with Childcare

Tonight
Dec 21 - Dec 22
Tomorrow
Dec 22 - Dec 23
Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
No exact matches found, but these alternatives could be just right

Recommended hotels in The Berkshires

Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2181)
"Awesome for ski"
United States
Lazar
The price is P6,105
P7,464 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Vacation Village in the Berkshires
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1004)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is P4,941
P5,520 total
includes taxes & fees
Jan 3 - Jan 4, 2026
The Yankee, Trademark Collection by Wyndham
Property amenity
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (804)
"Convenient location, very roomy, well equipped kitchen. "
United States
Carolyn
The price is P7,505
P9,531 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Lobby lounge
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (817)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is P6,439
P7,192 total
includes taxes & fees
Dec 22 - Dec 23
Berkshires Untold
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1004)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is P5,890
P6,579 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (994)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is P5,444
P6,080 total
includes taxes & fees
Dec 23 - Dec 24
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (592)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is P8,162
P9,117 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Courtyard by Marriott Lenox Berkshires
Lobby
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (13)
"New hotel very nice"
United States
joel
The price is P7,927
P8,855 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Element Lenox Berkshires
Lobby lounge
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is P6,154
P6,874 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn & Suites Berkshires-Lenox
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (709)
"Great hospitality "
United States
regina maria
The price is P6,283
P7,018 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"A magical, magical New England weekend at The Red Lion Inn. The room was so warm, the bed and pillows were so comfortable and just the right firmness. The pool and hot tube were open, maybe bring a swimsuit if you are up for a soak in the hot tub on a cold snowy day or night. Check in was a breeze, staff were warm and welcoming. Highly recommend making reservations at their Tavern or Dining Area. Several small cafes and charming local shops close by for Christmas shopping"
Judith Pauline 1-night trip
Posted 6 days ago
The Red Lion Inn

Frequently asked questions

How much do hotels with childcare in The Berkshires cost?
Rates for hotels with childcare in The Berkshires range between P5,520 and P9,531 per night. Whatever your budget, you'll find a comfy place with babysitting at an affordable price. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best hotels with childcare in The Berkshires?
Enjoy some "me" time while the kids get taken care of in one of The Berkshires's multiple hotels with childcare. With a total average guest review rating of 8.9, there's a place to suit every vacationing family. If you're arranging a trip to Lenox, Holiday Inn Club Vacations Oak 'n Spruce Resort comes highly recommended. This 2-star hotel offers babysitting services, a nightclub and a tennis court. Another family favorite in this popular destination is Seven Hills Inn. It has a 2-star rating and features a swimming pool and childcare services.
How many hotels with childcare are there in The Berkshires?
Pick from 5 hotels with childcare in The Berkshires. At these retreats, you can slip away for some "me" time while someone else entertains and supervises the kids!
Why book your hotel with childcare in The Berkshires with Expedia?
Book with Expedia and get access to the most popular hotels with childcare in The Berkshires at fabulous prices. Add on exclusive member discounts and free cancellation on many hotels (because flexibility matters, especially when traveling with kiddos!) and you've got yourself a hassle-free vacation to look forward to.
How can I find cheap hotels with childcare in The Berkshires?
If you're on the hunt for amazing deals on hotels with childcare in The Berkshires, implement a few filters into your search. Click on our "family friendly" filter to compare accommodations that have the services and amenities you need, like babysitting. Then, choose your budget and preferred hotel star rating. You can also sort your results by price so that the cheapest options show up first.
What is there to do in The Berkshires near my hotel with childcare?
One of the best travel accessories for your The Berkshires adventure is a well-designed itinerary! Sterling and Francine Clark Art Institute, Williams College Museum of Art and Hopkins Observatory are among the leading sights if you're bound for Williamstown. Pittsfield is also home to superb attractions, such as Bousquet Ski Area. Want to explore more? Stop by Barrington Stage Company and Berkshire Museum too.

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