Family friendly Hotels in Lee, Massachusetts

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Check availability on Lee Family friendly Hotels

Tonight
Nov 22 - Nov 23
Tomorrow
Nov 23 - Nov 24
Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7

Top Lee Family friendly Hotels

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
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
  • Cribs/infant beds provided
  • Indoor pool
8.0 out of 10, Very Good, (965)
Spacious suites accommodate families with comfort, while children splash in the heated indoor pool year-round. Located steps from Berkshire Museum, this hotel offers complimentary cribs and rollaway beds, alongside a restaurant serving delicious meals for hungry explorers.
The price is P4,896
P5,469 total
includes taxes & fees
Dec 22 - Dec 23
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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, (1007)
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
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
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
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
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
  • Cribs/infant beds provided
  • Indoor pool
9.2 out of 10, Wonderful, (587)
Splash into adventure at this welcoming retreat, where the indoor swimming pool provides year-round fun while Netflix and premium channels entertain after outdoor explorations. Located just 6 minutes from Bousquet Ski Area, families enjoy complimentary cribs and parking.
The price is P6,944
P7,756 total
includes taxes & fees
Dec 14 - Dec 15
Courtyard by Marriott Lenox Berkshires
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 P5,837
P6,520 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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 24 - Nov 25
Travelodge by Wyndham Great Barrington Berkshires
Arcade
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
  • Cribs/infant beds provided
  • 2 outdoor pools
  • Arcade/game room
9.0 out of 10, Wonderful, (789)
The price is P6,267
P7,822 total
includes taxes & fees
Nov 30 - Dec 1
Holiday Inn Club Vacations Oak n’ Spruce Resort in the 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 Lee Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"The room was nice, but wish we would have asked for the lake view. The breakfast area was really nice and they had good food. The coffee machine was available 24/7 and it made a pretty good mocha! "
terri 1-night trip
Posted 10 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Quality Inn

Quality Inn

10/10 Excellent
"Everything great but breakfast needs an overhaul. Fresh fruit get rid of the sugar cereals. Eggs maybe? "
John 2-night trip
Posted 1 month ago
Quality Inn

Frequently asked questions

What's Lee like for family-friendly vacations?
The destination of Lee is a great choice if you've been thinking about a vacation with your kids. The lake views, museums, and libraries are just some of the things that make this an attractive family vacation spot. Take to the air and fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest airport, or Hudson, NY (HCC-Columbia County), which is located 23.7 mi (38.2 km) from the city center.
What's the best accommodation for a family vacation to Lee?
The Black Swan Lee - Lenox, an Ascend Collection Hotel is a hotel with a restaurant and free parking, and it's a top choice on Expedia for families. Econo Lodge Lee - Great Barrington is another good choice for your stay with the kids.
When's the best time to book a family-friendly vacation in Lee?
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 27°F. The snowiest months in Lee 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 Lee?
While you are vacationing in Lee, you and the family might want to see interesting spots such as Berkshire Mountain Country Store and Lee Premium Outlets. Make sure you have lots of time for activities like Lee Library and Wood's Pond.