TOP Family Friendly Hotels in Lee for 2026 - 𝗙𝗿𝗲𝗲 𝗖𝗮𝗻𝗰𝗲𝗹𝗹𝗮𝘁𝗶𝗼𝗻 on Select Hotels | Expedia Singapore

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

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Check availability on Lee Family friendly Hotels

Tonight

12 Oct - 13 Oct

Tomorrow

13 Oct - 14 Oct

This weekend

16 Oct - 18 Oct

Next weekend

23 Oct - 25 Oct

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 dining area with large windows, wooden furniture, and a view of a lake.

A lakeside lodge with a dock, fishing rods, and outdoor seating.

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

Lee

Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.

S$164

includes taxes & fees

8 Nov - 9 Nov

A room with a foosball table, arcade games, and a large dartboard.

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 building with a porch and multiple windows, surrounded by purple flowers.

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

South Lee

S$192

includes taxes & fees

14 Oct - 15 Oct

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

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.

A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.

3. The Yankee Inn

Lenox

Family escape with indoor and outdoor pools—enjoy year-round swimming plus convenient ski access at Bousquet Ski Area.

S$152

includes taxes & fees

1 Nov - 2 Nov

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

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.

4. Courtyard by Marriott Lenox Berkshires

Lenox

Family memories made easy with an indoor pool, firepit, and cosy spaces just minutes from Bousquet Ski Area.

S$180

includes taxes & fees

1 Nov - 2 Nov

A modern hotel lobby with seating areas, tables, and a reception desk.

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.

A modern bathroom with a large mirror, a sink, and a shower.

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

Great Barrington

S$119

includes taxes & fees

10 Nov - 11 Nov

A room with multiple arcade games, including 'American Idol' and 'Toy Taxi'.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

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

Great Barrington

Families splash into fun at this Berkshires hotel with indoor pool, game arcade, and cosy rooms—all nestled near Ski Butternut.

S$205

includes taxes & fees

2 Nov - 3 Nov

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.

A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.

A standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.

7. Sunset Inn

Lee

Sunset Inn offers lakeside fun with seasonal pools and water activities for family memories.

S$127

includes taxes & fees

26 Oct - 27 Oct

A snow-covered outdoor area with a patio, seating, and a covered dining area.

A dining area with a glass table, red walls, and framed artwork.

A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

8. The Cornell Inn, Lenox & The Berkshires

Lenox

Family-friendly Cornell Inn offers free breakfast and garden setting near skiing and Tanglewood.

S$225

includes taxes & fees

27 Oct - 28 Oct

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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 dining area with large windows, wooden furniture, and a view of a lake.

A lakeside lodge with a dock, fishing rods, and outdoor seating.

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

S$164

includes taxes & fees

8 Nov - 9 Nov

A building with a porch and multiple windows, surrounded by purple flowers.

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

A living room with a sofa, armchair, coffee table, and a patterned rug.

A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

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

South Lee

S$192

includes taxes & fees

14 Oct - 15 Oct

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

The Yankee Inn

Lenox

S$152

includes taxes & fees

1 Nov - 2 Nov

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

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

Lenox

S$180

includes taxes & fees

1 Nov - 2 Nov

A modern hotel lobby with seating areas, tables, and a reception desk.

A hotel room with two beds, a desk, a TV, and a window with curtains.

A kitchenette with a microwave, coffee maker, and coffee cups.

A breakfast area with a counter, coffee machine, and a display of pastries.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

S$119

includes taxes & fees

10 Nov - 11 Nov

A snow-covered outdoor area with a patio, seating, and a covered dining area.

A dining area with a glass table, red walls, and framed artwork.

A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

The Cornell Inn, Lenox & The Berkshires

Lenox

S$225

includes taxes & fees

27 Oct - 28 Oct

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

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

Great Barrington

S$205

includes taxes & fees

2 Nov - 3 Nov

A hotel patio with outdoor seating and a fire pit.

A spacious living room with a large sofa, a coffee table, and a fireplace.

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

Exterior

Hilton Garden Inn Lenox Pittsfield

Pittsfield

S$183

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

An outdoor seating area with Adirondack chairs and a fire feature.

A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

Element by Marriott Lenox Berkshires

Lenox

S$205

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a bed, a desk, and two wall-mounted lamps.

A motel with a central entrance, a flag, and a parking area with several cars.

A hotel reception desk with an orange counter, a computer, a beverage cooler, and framed awards on the wall.

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

Lee

S$94

includes taxes & fees

6 Nov - 7 Nov

View all properties

Family-friendly hotels with pools in Lee

A building with a porch and multiple windows, surrounded by purple flowers.

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

A living room with a sofa, armchair, coffee table, and a patterned rug.

A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

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

South Lee

S$192

includes taxes & fees

14 Oct - 15 Oct

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

The Yankee Inn

Lenox

S$152

includes taxes & fees

1 Nov - 2 Nov

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

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

Lenox

S$180

includes taxes & fees

1 Nov - 2 Nov

A modern hotel lobby with seating areas, tables, and a reception desk.

A hotel room with two beds, a desk, a TV, and a window with curtains.

A kitchenette with a microwave, coffee maker, and coffee cups.

A breakfast area with a counter, coffee machine, and a display of pastries.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

S$119

includes taxes & fees

10 Nov - 11 Nov

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

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

Great Barrington

S$205

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

An outdoor seating area with Adirondack chairs and a fire feature.

A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

Element by Marriott Lenox Berkshires

Lenox

S$205

includes taxes & fees

8 Nov - 9 Nov

A hotel patio with outdoor seating and a fire pit.

A spacious living room with a large sofa, a coffee table, and a fireplace.

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

Exterior

Hilton Garden Inn Lenox Pittsfield

Pittsfield

S$183

includes taxes & fees

1 Nov - 2 Nov

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

A spacious lobby with a fireplace, seating area, and a bar.

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

Berkshire Mountain Lodge

Pittsfield

S$151

includes taxes & fees

9 Nov - 10 Nov

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.

A swimming pool with a fenced area, lounge chairs, and a warning sign.

A standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.

Sunset Inn

Lee

S$127

includes taxes & fees

26 Oct - 27 Oct

Front of property

A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.

A stone fountain surrounded by trees in a park setting.

Exterior

The Inn at Stockbridge

Stockbridge

S$548

includes taxes & fees

1 Nov - 2 Nov

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

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."

Devonfield Inn B&B

Devonfield Inn B&B

10/10 Excellent

"Wonderful location and hosts are amazing. Breakfast was great. Clean."

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.

What's the best family accommodation in 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 option for your family trip.

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.

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