Find Family Hotels in Great Barrington, MA

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Great Barrington Family Hotels

Our top choices for Great Barrington family-friendly hotels

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 NT$3,836
NT$4,902 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Club Vacations Oak n’ Spruce Resort in the 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, (989)
"Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful . "
United States
Dwight
The price is NT$2,923
NT$3,265 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (1001)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is NT$3,163
NT$3,534 total
includes taxes & fees
Jan 8 - 2026/1/9
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (562)
"The staff were very friendly and accommodating "
United States
Tom
The price is NT$2,365
NT$2,642 total
includes taxes & fees
Dec 21 - Dec 22
Travelodge by Wyndham Great Barrington Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (758)
"Clean room, very courteous staff "
United States
Thomas
The price is NT$4,257
NT$4,755 total
includes taxes & fees
Jan 19 - 2026/1/20
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is NT$7,947
NT$9,934 total
includes taxes & fees
Dec 21 - Dec 22
Prospect 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 NT$4,258
NT$4,756 total
includes taxes & fees
Jan 4 - 2026/1/5
Element Lenox Berkshires

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1001)
"Very friendly and good Breakfast."
United States
Jesse
The price is NT$2,388
NT$2,667 total
includes taxes & fees
Dec 22 - Dec 23
Best Western Plus Berkshire Hills Inn & Suites

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (65)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is NT$3,566
NT$3,983 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is NT$12,044
NT$14,570 total
includes taxes & fees
Jan 19 - 2026/1/20
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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.

Find out more about Great Barrington

Family friendly things to do in Great Barrington

Great Barrington, Massachusetts, offers a charming mix of outdoor adventures and cultural experiences perfect for families. Start your day at the picturesque Lake Mansfield, where children can splash in the water, and parents can enjoy a scenic picnic or take a stroll along the nature trails. Next, head over to the Berkshire Botanical Garden, where kids can explore beautiful gardens and participate in seasonal family programs that inspire a love for nature. For a dose of adventure, visit Catamount Ski Area, which not only offers skiing in the winter but also features a thrilling zip line and mountain coaster during the summer months, making it a year-round destination for family fun. Art lovers will appreciate the Norman Rockwell Museum, where interactive exhibits and family-friendly activities bring the iconic artist's work to life, sparking creativity in young minds. Finally, unwind in the vibrant downtown area filled with locally-owned shops and eateries, providing a relaxed atmosphere for families to enjoy together. For accommodation, consider staying at family-friendly hotels near Main Street, where you can easily access these attractions while enjoying comfortable rooms and amenities tailored for families, like spacious suites and pools. This area not only makes exploring effortless but also offers a welcoming place where attentive service ensures your family feels right at home.

Find the best family friendly hotels in Great Barrington

For families planning a visit to Great Barrington, Massachusetts, these hotels offer a range of family-friendly amenities to ensure a comfortable and enjoyable stay. Each hotel is designed with families in mind, providing everything from spacious rooms to activities.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

  • Why it's great for a family-friendly adventure: Perfect for families, the Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires features a stellar review rating of 9.4, showcasing its commitment to guest satisfaction. Families will appreciate the accessible indoor pool, connecting rooms for added space, and the convenience of microwaves and sofa beds in their accommodations, making it an excellent choice for all ages.
  • Other amenities: In addition to family-friendly amenities, guests can enjoy a variety of amenities that enhance their stay. Daily housekeeping ensures a clean and comfortable environment, while complimentary breakfast options including a full and continental breakfast cater to hungry travelers. Outdoor activities with nearby skiing and snow tubing, plus a fitness center for active guests. The hotel also boasts free self-parking and easy access to shopping and hiking opportunities.
  • Nearby attractions: Housatonic River - 0.3 miles, Mahaiwe Performing Arts Center - 1.64 miles, Housatonic River Walk - 1.33 miles

Holiday Inn Express Hotel & Suites Great Barrington by IHG

  • Why it's great for a family-friendly adventure: The Holiday Inn Express Hotel & Suites Great Barrington is an ideal family-friendly destination, a solid review rating of 8.8. Families will benefit from spacious rooms featuring free cribs, connecting rooms, and convenient amenities like microwaves and mini-refrigerators to make their stay comfortable and enjoyable.
  • Other amenities: Guests can start each day with a complimentary buffet breakfast, ensuring everyone is fueled for their adventures. The inviting indoor pool is perfect for family fun, while the nearby skiing options provide exciting winter activities. Additional features include air conditioning, separate living rooms, and free self-parking, making this hotel a practical choice for family travelers.
  • Nearby attractions: Housatonic River - 0.06 miles, Mahaiwe Performing Arts Center - 2.09 miles, Housatonic River Walk - 1.78 miles

Monument Mountain Motel

  • Why it's great for a family-friendly adventure: Families seeking a cozy retreat will find Monument Mountain Motel a great option, with an excellent review rating of 8.8. This charming motel prioritizes family comfort with free cribs and a playground for children, providing a welcoming atmosphere for guests of all ages.
  • Other amenities: Beyond family-centric amenities, guests can enjoy additional features such as daily housekeeping and microwaves in their rooms. The motel is conveniently located near skiing areas for winter fun, and offers free self-parking for added convenience. Air conditioning ensures a comfortable stay throughout the year, making it a well-rounded choice for family getaways.
  • Nearby attractions: Housatonic River - 0.18 miles, Mahaiwe Performing Arts Center - 1.6 miles, Housatonic River Walk - 1.29 miles

The Little Lion

  • Why it's great for a family-friendly adventure: The Little Lion is a delightful option for families, earning an excellent review rating of 8.6. This hotel offers convenient amenities such as free cribs, connecting rooms, and a sofa bed, making it a comfortable base for families exploring Great Barrington.
  • Other amenities: Guests can take advantage of daily housekeeping services and enjoy the lovely garden area, perfect for outdoor relaxation. Additional amenities include air conditioning for comfortable stays, free self-parking, and nearby skiing activities for family fun. With a welcoming atmosphere, The Little Lion is an excellent choice for family travelers.
  • Nearby attractions: Housatonic River - 1.33 miles, Schantz Galleries - 3.21 miles

Quality Inn

  • Why it's great for a family-friendly adventure: Quality Inn offers a welcoming place for families, with a positive review rating of 8.2. Families will appreciate the availability of connecting rooms and daily housekeeping, ensuring a comfortable stay while providing flexibility for larger groups or families.
  • Other amenities: In addition to family-friendly amenities, the hotel features free breakfast options to start each day right. Guests can enjoy outdoor activities with nearby skiing and snow tubing, along with free self-parking for ease of travel. The hotel also offers late check-out and early check-in for added convenience, alongside premium bedding for a restful night’s sleep.
  • Nearby attractions: Housatonic River - 0.38 miles, Mahaiwe Performing Arts Center - 0.22 miles, Housatonic River Walk - 0.44 miles

Top Great Barrington Hotel Reviews

Frequently asked questions

What's Great Barrington like for family-friendly vacations?
If you've been thinking about a vacation with your kids, Great Barrington is a good choice. The entertainment, cafes, and hiking trails are just a few things that make this an attractive spot for a family vacation. Arrange a flight into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 16.2 mi (26.1 km) from the city center.
What's the best accommodation for a family trip to Great Barrington?
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires is a hotel with an indoor pool and free parking, and it's a top choice on Expedia for families. Travelodge by Wyndham Great Barrington Berkshires is another good option for your family trip.
When's the best time to book a family-friendly vacation in Great Barrington?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Great Barrington are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's there to see and do with your family in Great Barrington?
While you are visiting Great Barrington, you might want to round up the kiddos and make time to see interesting attractions such as Mahaiwe Performing Arts Center and Ski Butternut. Make sure you have lots of time for activities like Catamount Ski Area and Art et Industrie.

Explore a world of travel with Expedia