Family friendly Hotels in Great Barrington, Massachusetts

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Check availability on Great Barrington Family friendly Hotels

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Nov 22 - Nov 23
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Nov 23 - Nov 24
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Nov 28 - Nov 30
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Dec 5 - Dec 7

Top Great Barrington Family friendly Hotels

Property amenity
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
Great Barrington
  • Cribs/infant beds provided
  • Arcade/game room
9.4 out of 10, Exceptional, (755)
Vibrant game room captivates young adventurers while parents unwind in the soundproof accommodations or hot tub. After complimentary breakfast, families explore nearby skiing or Housatonic River Walk, returning to swim sessions in the pristine indoor pool.
The price is P8,885
P9,925 total
includes taxes & fees
Nov 30 - Dec 1
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
  • Outdoor pool
9.6 out of 10, Exceptional, (14)
The price is P15,299
P19,061 total
includes taxes & fees
Nov 24 - Nov 25
Prospect Berkshires
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
Great Barrington
  • Cribs/infant beds provided
7.6 out of 10, Good, (560)
Family vacations shine at this peaceful Berkshire retreat offering complimentary cribs and rollaway beds for little ones. The refreshing pool delights with sunny and shaded areas, while the spotless accommodations and helpful staff ensure carefree comfort for travelers of all ages.
The price is P4,413
P4,930 total
includes taxes & fees
Nov 23 - Nov 24
Travelodge by Wyndham Great Barrington Berkshires
Indoor wedding
Gedney Farm

Gedney Farm

3.5 star property
Great Barrington
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
9.2 out of 10, Wonderful, (132)
The price is P10,915
P11,974 total
includes taxes & fees
Dec 22 - Dec 23
Gedney Farm
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.8 out of 10, Exceptional, (11)
The price is P7,709
P8,610 total
includes taxes & fees
Dec 11 - Dec 12
Element Lenox Berkshires
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
  • Cribs/infant beds
8.6 out of 10, Excellent, (1001)
Family memories await at this thoughtful property, featuring spacious suites with premium TV channels and blackout drapes for restful evenings. Complimentary breakfast fuels adventures before heading to nearby Bousquet Ski Area, just a quick 5-minute drive away.
The price is P5,501
P6,144 total
includes taxes & fees
Nov 24 - Nov 25
Best Western Plus Berkshire Hills Inn & Suites
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
  • Cribs/infant beds provided
9.0 out of 10, Wonderful, (1001)
Playtime paradise awaits with free cribs, kayaking on the sparkling lake, and motor boating adventures. Children delight in fishing excursions, premium TV entertainment, and beachside fun while parents appreciate the lakefront setting and complimentary breakfast each morning.
The price is P6,252
P6,984 total
includes taxes & fees
Dec 14 - Dec 15
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Indoor pool
9.2 out of 10, Wonderful, (1006)
Splash into family fun at this hotel with dual pools, kid-friendly supervised swimming, and microwaves for quick snacks. Just a 3-minute drive from Bousquet Ski Area, the property combines mountain scenery with cozy rooms featuring cable TV and essential comforts.
The price is P4,366
P4,877 total
includes taxes & fees
Dec 14 - Dec 15
The Yankee, Trademark Collection by Wyndham
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
  • Cribs/infant beds provided
  • Indoor pool
9.4 out of 10, Exceptional, (60)
Vacation-ready accommodations feature premium TV channels and complimentary cribs for little travelers. Mornings begin with a free breakfast buffet, fueling adventures to nearby attractions. Spotlessly clean facilities and cheerful staff ensure a relaxing family retreat.
The price is P5,858
P6,543 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Pittsfield - Berkshires 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.
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Top Great Barrington Hotel Reviews

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

10/10 Excellent
"Very nice people at the desk, room was very nice"
Joseph 1-night trip
Posted 14 hours ago
Travelodge by Wyndham Great Barrington Berkshires

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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.