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

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Check availability on Lee Family Hotels

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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.
A lakeside dock with kayaks and a covered boat ramp.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A lodge with a large building and a dock by a lake, surrounded by forest.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
  • Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
NT$3,647
NT$4,074 total
includes taxes & fees
Nov 15 - Nov 16
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A room with a foosball table, arcade games, and a large dartboard.
A building with a porch and multiple windows, surrounded by purple flowers.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A living room with a sofa, armchair, coffee table, and a patterned rug.

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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
NT$3,791
NT$4,868 total
includes taxes & fees
Oct 26 - Oct 27
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A covered outdoor area with stone pillars and a view of a road and green hills.

3. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
  • Family memories made easy with an indoor pool, firepit, and cozy spaces just minutes from Bousquet Ski Area.
NT$4,070
NT$4,546 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

4. The Yankee Inn

The Yankee Inn
Lenox
  • Family escape with indoor and outdoor pools—enjoy year-round swimming plus convenient ski access at Bousquet Ski Area.
NT$3,435
NT$3,836 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.

5. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
  • Family-friendly Cornell Inn offers free breakfast and garden setting near skiing and Tanglewood.
NT$4,972
NT$5,703 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
A room with multiple arcade games, including 'American Idol' and 'Toy Taxi'.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
  • Families splash into fun at this Berkshires hotel with indoor pool, game arcade, and cozy rooms—all nestled near Ski Butternut.
NT$4,654
NT$5,199 total
includes taxes & fees
Nov 4 - Nov 5
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A hotel patio with outdoor seating and a fire pit.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.
A spacious living room with a large sofa, a coffee table, and a fireplace.

7. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
NT$4,143
NT$4,628 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
A modern hotel lobby with seating areas, tables, and a reception desk.
A modern bathroom with a large mirror, a sink, and a shower.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A coffee station with two coffee machines and a variety of coffee pods and cups.

8. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
NT$2,698
NT$3,014 total
includes taxes & fees
Nov 17 - Nov 18
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A Scrabble game on a wooden table with a vase of flowers and a cup.
A bar area with wooden shelves, green bar stools, and a variety of bottles and glasses.
A cozy library with bookshelves, a fireplace, and comfortable seating.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

9. Berkshires Untold

Berkshires Untold
Lenox
NT$4,218
NT$4,712 total
includes taxes & fees
Nov 1 - Nov 2
Berkshires Untold
A swimming pool with a fenced area, lounge chairs, and a warning sign.
A covered corridor with a metal railing, white walls, and a view of a street with parked cars.
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.
A hotel room with two beds, a chair, and a bedside table with a phone.

10. Sunset Inn

Sunset Inn
Lee
  • Sunset Inn offers lakeside fun with seasonal pools and water activities for family memories.
NT$2,624
NT$2,932 total
includes taxes & fees
Nov 1 - Nov 2
Sunset Inn
View all properties

Choose what matters most at family-friendly hotels in Lee

Breakfast included
Pool
All-inclusive
4 stars
5 stars

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.
A lakeside dock with kayaks and a covered boat ramp.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A lodge with a large building and a dock by a lake, surrounded by forest.

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
NT$3,647
NT$4,074 total
includes taxes & fees
Nov 15 - Nov 16
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.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A covered outdoor area with stone pillars and a view of a road and green hills.

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
NT$4,070
NT$4,546 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
A building with a porch and multiple windows, surrounded by purple flowers.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A café with a display case, a frozen food section, and a marketplace sign.

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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
NT$3,791
NT$4,868 total
includes taxes & fees
Oct 26 - Oct 27
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

The Yankee Inn

The Yankee Inn
Lenox
NT$3,435
NT$3,836 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
NT$4,972
NT$5,703 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
NT$4,654
NT$5,199 total
includes taxes & fees
Nov 4 - Nov 5
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A modern cafe with a counter, seating area, and large windows.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
NT$3,088
NT$3,450 total
includes taxes & fees
Nov 17 - Nov 18
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A hotel patio with outdoor seating and a fire pit.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.
A spacious living room with a large sofa, a coffee table, and a fireplace.

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
NT$4,143
NT$4,628 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
Front of property
A stone fountain surrounded by trees in a park setting.
A living room with a fireplace, leather sofas, and a dog.
Exterior

The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
NT$11,819
NT$13,862 total
includes taxes & fees
Nov 1 - Nov 2
The Inn at Stockbridge
A hotel room with a bed, a desk, and two wall-mounted lamps.
A hotel reception desk with an orange counter, a computer, a beverage cooler, and framed awards on the wall.
A motel with a flagpole, a blue awning, and a parking lot.
A hotel room with a bed, two bedside tables, a desk, two chairs, and a large window with a view of greenery.

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
Lee
NT$2,128
NT$2,377 total
includes taxes & fees
Nov 13 - Nov 14
Econo Lodge Lee - Great Barrington
View all properties

Family-friendly hotels with pools in Lee

A building with a porch and multiple windows, surrounded by purple flowers.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A café with a display case, a frozen food section, and a marketplace sign.

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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
NT$3,791
NT$4,868 total
includes taxes & fees
Oct 26 - Oct 27
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A covered outdoor area with stone pillars and a view of a road and green hills.

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
NT$4,070
NT$4,546 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

The Yankee Inn

The Yankee Inn
Lenox
NT$3,435
NT$3,836 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
NT$4,654
NT$5,199 total
includes taxes & fees
Nov 4 - Nov 5
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A hotel patio with outdoor seating and a fire pit.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.
A spacious living room with a large sofa, a coffee table, and a fireplace.

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
NT$4,143
NT$4,628 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A garden with wooden Adirondack chairs and a stone pathway.
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
NT$2,804
NT$3,856 total
includes taxes & fees
Nov 10 - Nov 11
Berkshire Mountain Lodge
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A modern cafe with a counter, seating area, and large windows.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
NT$3,088
NT$3,450 total
includes taxes & fees
Nov 17 - Nov 18
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Front of property
A stone fountain surrounded by trees in a park setting.
A living room with a fireplace, leather sofas, and a dog.
Exterior

The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
NT$11,819
NT$13,862 total
includes taxes & fees
Nov 1 - Nov 2
The Inn at Stockbridge
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.
A covered corridor with a metal railing, white walls, and a view of a street with parked cars.
A swimming pool with a fenced area, lounge chairs, and a warning sign.
A hotel room with two beds, a chair, and a bedside table with a phone.

Sunset Inn

Sunset Inn
Lee
NT$2,624
NT$2,932 total
includes taxes & fees
Nov 1 - Nov 2
Sunset Inn
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.
A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
NT$2,560
NT$2,859 total
includes taxes & fees
Oct 22 - Oct 23
Howard Johnson by Wyndham Lenox
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

Sunset Inn

Sunset Inn

8/10 Good
"We were in town for a show at Tanglewood in Lenox. Concert had been rescheduled with little notice; so it put us in a tight spot with no time to add time to being in the Berkshires. I just looked for an inexpensive overnight to just sleep before heading back home the following morning. I wasn't expecting much. We were pleasantly surprised. Our little room was clean and felt safe. We could open the windows! The bed and pillows were very comfortable. We slept great. The location was perfect; walked into town for a really good meal before heading to the show. The following morning breakfast restaurant just doors away was incredible! This hotel is out of the 60's in its character and charm. The one man operation is very efficient in responding to the check-in buzzer and to answering the phone for a quick question. We didn't use the shower or the TV; so I can't say anything about that."
Ellen 1-night trip
Posted 1 month ago
Sunset Inn
Devonfield Inn B&B

Devonfield Inn B&B

10/10 Excellent
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
Sebastien 2-night trip
Posted 1 month ago
Devonfield Inn B&B

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.

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