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Check prices for these dates

Tonight
12 Nov - 13 Nov
Tomorrow
13 Nov - 14 Nov
This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 Nov

Our top choices for Lee family-friendly hotels

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

1. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
The price is AED 390
AED 436 total
includes taxes & fees
13 Dec - 14 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Two Adirondack chairs facing a river with a forested hill in the background.

2. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Family escape with indoor and outdoor pools—enjoy year-round swimming plus convenient ski access at Bousquet Ski Area.
The price is AED 438
AED 489 total
includes taxes & fees
17 Nov - 18 Nov
The Yankee Inn
An indoor arcade with various gaming machines, a ping pong table, and a vending machine.

3. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,000 reviews)
The price is AED 430
AED 552 total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A snow-covered outdoor area with a patio, seating, and a covered dining area.

4. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,000 reviews)
  • cleanliness
    Family-friendly Cornell Inn offers free breakfast and garden setting near skiing and Tanglewood.
The price is AED 624
AED 716 total
includes taxes & fees
15 Nov - 16 Nov
The Cornell Inn, Lenox & The Berkshires
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

5. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (690 reviews)
  • cleanliness
    Family memories made easy with an indoor pool, firepit, and cozy spaces just minutes from Bousquet Ski Area.
The price is AED 418
AED 467 total
includes taxes & fees
13 Dec - 14 Dec
Courtyard by Marriott Lenox Berkshires
A garden with a gazebo, a table, chairs, and potted plants.

6. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (110 reviews)
The price is AED 847
AED 993 total
includes taxes & fees
15 Nov - 16 Nov
The Inn at Stockbridge
An indoor swimming pool with clear water, tiled floors, and a blue wall.

7. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (258 reviews)
  • cleanliness
    Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Center.
The price is AED 378
AED 423 total
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

8. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (718 reviews)
The price is AED 436
AED 487 total
includes taxes & fees
15 Nov - 16 Nov
Hilton Garden Inn Lenox Pittsfield
A room with multiple arcade games, including 'American Idol' and 'Toy Taxi'.

9. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (822 reviews)
  • cleanliness
    Families splash into fun at this Berkshires hotel with indoor pool, game arcade, and cozy rooms—all nestled near Ski Butternut.
The price is AED 590
AED 659 total
includes taxes & fees
16 Nov - 17 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A Scrabble game on a wooden table with a vase of flowers and a cup.

10. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,074 reviews)
The price is AED 386
AED 431 total
includes taxes & fees
17 Nov - 18 Nov
Berkshires Untold
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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Choose what matters most at family-friendly hotels in Lee

Breakfast included
Pool

Family-friendly hotels with free breakfast in Lee

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
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
9.2 out of 10, Wonderful, (1001)
The price is AED 390
AED 436 total
includes taxes & fees
13 Dec - 14 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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Family-friendly hotels with pools in Lee

A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1000)
The price is AED 430
AED 552 total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
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

A bookshelf with various books and games, a 'RELAX' sign, and two red pillows on a bench.
Hotel On North

Hotel On North

Hotel On North
Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...
United States
Steve
Reviewed February 28, 2016
Hotel On North

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 Lee Premium Outlets and Lee Library. Make sure you have lots of time for activities like Berkshire Mountain Country Store and Animagic Museum of Animation.