A street lined with historic buildings, including a Morgan House restaurant.

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Check availability on Lee Family-Friendly Hotels

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 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, (1,013 reviews)
  • cleanliness
    Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
The price is 2.834.014 ₫
3.165.594 ₫ total
includes taxes & fees
22 Nov - 23 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

2. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (680 reviews)
  • cleanliness
    Family memories made easy with an indoor pool, firepit, and cosy spaces just minutes from Bousquet Ski Area.
The price is 3.245.888 ₫
3.625.657 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
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, (1,007 reviews)
The price is 3.023.982 ₫
3.883.077 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
Two Adirondack chairs facing a river with a forested hill in the background.

4. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,006 reviews)
  • cleanliness
    Family escape with indoor and outdoor pools—enjoy year-round swimming plus convenient ski access at Bousquet Ski Area.
The price is 2.739.146 ₫
3.059.574 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
A snow-covered outdoor area with a patio, seating, and a covered dining area.

5. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
  • cleanliness
    Family-friendly Cornell Inn offers free breakfast and garden setting near skiing and Tanglewood.
The price is 4.393.383 ₫
5.039.211 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The Cornell Inn, Lenox & The Berkshires
A Scrabble game on a wooden table with a vase of flowers and a cup.

6. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,053 reviews)
The price is 3.364.870 ₫
3.758.559 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Berkshires Untold
A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

7. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (715 reviews)
The price is 3.066.810 ₫
3.425.483 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Hilton Garden Inn Lenox Pittsfield
A swimming pool with a fenced area, lounge chairs, and a warning sign.

8. Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (447 reviews)
  • cleanliness
    Sunset Inn offers lakeside fun with seasonal pools and water activities for family memories.
The price is 2.093.121 ₫
2.338.016 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Sunset Inn
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, (818 reviews)
  • cleanliness
    Families splash into fun at this Berkshires hotel with indoor pool, game arcade, and cosy rooms—all nestled near Ski Butternut.
The price is 3.712.060 ₫
4.146.371 ₫ total
includes taxes & fees
4 Nov - 5 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A room with a pool table, arcade games, and seating areas.

10. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,233 reviews)
The price is 2.215.586 ₫
3.052.209 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Berkshire Mountain Lodge
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, (1013)
The price is 2.834.014 ₫
3.165.594 ₫ total
includes taxes & fees
22 Nov - 23 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
View all properties

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, (1007)
The price is 3.023.982 ₫
3.883.077 ₫ total
includes taxes & fees
29 Oct - 30 Oct
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.
View all properties

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
"Room was very clean and updated. We enjoyed the deck, although it needs some updating due to broken boards. I was told the restaurant was a fine place to dine. Desk staff was helpful."
Barbara 2-night trip
Posted 11 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Frequently asked questions

What's Lee like for family-friendly holidays?
The destination of Lee is a great choice if you've been thinking about a holiday with your children. The lake views, museums and libraries are just some of the things that make this an attractive spot for a family holiday. 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 centre.
When's the best time to book a family-friendly holiday in Lee?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Lee are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What's there to see and do with your family in Lee?
While you are holidaying in Lee, you and the family may want to see some interesting spots such as Lee Premium Outlets and Lee Library. Make sure that you have lots of time for activities such as Berkshire Mountain Country Store and Animagic Museum of Animation.