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Find Family-Friendly Hotels in The Berkshires, MA

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Check availability on The Berkshires Family-Friendly Hotels

Tonight
11 Oct - 12 Oct
Tomorrow
12 Oct - 13 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

Our top choices for The Berkshires family-friendly hotels

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
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.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

1. 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.
£89
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lodge with a large building and a dock by a lake, surrounded by forest.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A lakeside dock with kayaks and a covered boat ramp.

2. 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.
£100
includes taxes & fees
10 Nov - 11 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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 breakfast area with a counter, coffee machine, and a display of pastries.
A coffee station with two coffee machines and a variety of coffee pods and cups.

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
£70
includes taxes & fees
10 Nov - 11 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 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.

4. 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.
£133
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
A hotel room with a wooden dresser, a television, a microwave, and a mirror.
A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.
A row of white plastic chairs on a covered outdoor area with a white building in the background.

5. Monument Mountain Motel

Monument Mountain Motel
Great Barrington
£51
includes taxes & fees
1 Nov - 2 Nov
Monument Mountain Motel
A Scrabble game on a wooden table with a vase of flowers and a cup.
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".
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

6. Berkshires Untold

Berkshires Untold
Lenox
£110
includes taxes & fees
1 Nov - 2 Nov
Berkshires Untold
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 living room with a sofa, armchair, coffee table, and a patterned rug.

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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
£114
includes taxes & fees
14 Oct - 15 Oct
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.
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.

8. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
  • Family memories made easy with an indoor pool, firepit, and cosy spaces just minutes from Bousquet Ski Area.
£106
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
A bookshelf with various books and games, a 'RELAX' sign, and two red pillows on a bench.
A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.
A building entrance with a large planter with purple flowers and a small tree.
A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

9. Hotel On North

Hotel On North
Pittsfield
£113
includes taxes & fees
1 Nov - 2 Nov
Hotel On North
A room with a pool table, arcade games, and seating areas.
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.

10. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
£89
includes taxes & fees
9 Nov - 10 Nov
Berkshire Mountain Lodge
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Choose what matters most at family-friendly hotels in The Berkshires

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Family-friendly hotels with free breakfast in The Berkshires

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

The Yankee Inn

The Yankee Inn
Lenox
£89
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lodge with a large building and a dock by a lake, surrounded by forest.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A lakeside dock with kayaks and a covered boat ramp.

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
£100
includes taxes & fees
10 Nov - 11 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.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
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.

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
£106
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
A modern hotel lobby with seating areas, tables, and a reception desk.
A breakfast area with a counter, coffee machine, and a display of pastries.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A kitchenette with a microwave, coffee maker, and coffee cups.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
£70
includes taxes & fees
10 Nov - 11 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 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.

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
£133
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
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.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
£121
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 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
£114
includes taxes & fees
14 Oct - 15 Oct
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
A hotel patio with outdoor seating and a fire pit.
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
£108
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Lenox Pittsfield
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
£121
includes taxes & fees
8 Nov - 9 Nov
Element by Marriott Lenox Berkshires
A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.
A reception area with a large landscape painting, a dark reception desk, and a potted plant.
A modern cafe with a wooden accent wall, a coffee machine, and black chairs.
A modern hotel building with the name "Hotel Downtown" on the facade.

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
£101
includes taxes & fees
1 Nov - 2 Nov
Hotel Downstreet, an Ascend Collection Hotel
View all properties

Family-friendly hotels with pools in The Berkshires

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

The Yankee Inn

The Yankee Inn
Lenox
£89
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
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.
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.

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
£106
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
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.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
£121
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 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
£114
includes taxes & fees
14 Oct - 15 Oct
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A modern hotel lobby with seating areas, tables, and a reception desk.
A breakfast area with a counter, coffee machine, and a display of pastries.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A kitchenette with a microwave, coffee maker, and coffee cups.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
£70
includes taxes & fees
10 Nov - 11 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A spacious lobby with a fireplace, seating area, and a bar.
A garden with wooden Adirondack chairs and a stone pathway.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
£89
includes taxes & fees
9 Nov - 10 Nov
Berkshire Mountain Lodge
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
£121
includes taxes & fees
8 Nov - 9 Nov
Element by Marriott Lenox Berkshires
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
A hotel patio with outdoor seating and a fire pit.
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
£108
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Lenox Pittsfield
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.
Indoor pool
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.
A spacious living room with large windows, a fireplace, and a variety of seating options.

Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
£76
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
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 gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
£67
includes taxes & fees
18 Oct - 19 Oct
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.
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Find out more about The Berkshires

Family friendly things to do in The Berkshires

The Berkshires is a paradise of family-friendly activities that promise adventure and education for all ages. Start your journey at the Berkshire Museum in Pittsfield, where children can marvel at interactive exhibits, admire local art, and even meet live animals. For outdoor enthusiasts, the Bousquet Mountain offers skiing in winter and mountain biking in summer, ensuring thrill-seekers of all ages are entertained. Don’t miss the picturesque hiking trails at Mount Greylock State Reservation, which boasts stunning views and picnic spots perfect for family lunches. Arts lovers will appreciate the Tanglewood Music Center, where families can enjoy concerts in a stunning natural setting—some performances are even designed for children. Finally, the Norman Rockwell Museum in Stockbridge invites families to explore the life and works of one of America’s beloved illustrators, with activities tailored for young visitors. When it comes to accommodation, the area surrounding Lenox and Stockbridge features a range of family-friendly hotels that cater to your every need. Many establishments offer spacious suites, on-site dining, and activities like swimming pools and game rooms, ensuring that relaxation and fun go hand in hand. Staying here places you in close nearby top attractions, making it easy to explore without the hassle of long drives. The attentive service and comfortable amenities found in these hotels will make your family feel pampered, allowing for a seamless and enjoyable getaway in the beautiful Berkshires.

Top The Berkshires Hotel Reviews

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Our room was nice and clean. The suite is perfect. Can fix a cup of tea or a meal, everything you need just bring your food. A restaurant on site if you don't want to cook. Bed was comfortable with crisp white linens."
Anna 2-night trip
Posted 2 hours ago
Jiminy Peak Mountain Resort
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Beautiful location!"
Pofen 1-night trip
Posted 5 hours ago
Vacation Village in the Berkshires
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Lovely room, comfortable bed and a nice breakfast."
judith 1-night trip
Posted 1 day ago
The Cornell Inn, Lenox & The Berkshires
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good
"It was fine. No breakfast that I saw"
Michael 1-night trip
Posted 2 days ago
Best Western Plus Berkshire Hills Inn & Suites
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"
Joanne 1-night trip
Posted 5 days ago
The Red Lion Inn

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