10 Best Family Friendly Hotels in The Berkshires for 2026

A person snowboarding down a snowy slope.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on The Berkshires Family friendly Hotels

Tonight

Tomorrow

Next weekend

In two weeks

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

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

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

1. The Yankee Inn

Lenox

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

RM433

RM484 total

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.

A covered outdoor area with stone pillars and a view of a road and green hills.

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

2. Courtyard by Marriott Lenox Berkshires

Lenox

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

RM513

RM573 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

3. 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.

RM587

RM656 total

includes taxes & fees

2 Nov - 3 Nov

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

A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

A building entrance with a large planter with purple flowers and a small tree.

A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

4. Hotel On North

Pittsfield

RM548

RM612 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A lakeside dock with kayaks and a covered boat ramp.

A lodge with a large building and a dock by a lake, surrounded by forest.

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

Lee

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

RM483

RM539 total

includes taxes & fees

10 Nov - 11 Nov

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 bar area with wooden shelves, green bar stools, and a variety of bottles and glasses.

6. Berkshires Untold

Lenox

RM532

RM594 total

includes taxes & fees

1 Nov - 2 Nov

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

A modern living room with a fireplace, comfortable seating, and a large window with curtains.

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.

7. The Cornell Inn, Lenox & The Berkshires

Lenox

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

RM627

RM719 total

includes taxes & fees

27 Oct - 28 Oct

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 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

Great Barrington

RM339

RM379 total

includes taxes & fees

10 Nov - 11 Nov

View all properties

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

The Yankee Inn

Lenox

RM433

RM484 total

includes taxes & fees

1 Nov - 2 Nov

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

RM483

RM539 total

includes taxes & fees

10 Nov - 11 Nov

Courtyard by Marriott Lenox Berkshires

Lenox

RM513

RM573 total

includes taxes & fees

1 Nov - 2 Nov

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

RM339

RM379 total

includes taxes & fees

10 Nov - 11 Nov

The Cornell Inn, Lenox & The Berkshires

Lenox

RM627

RM719 total

includes taxes & fees

27 Oct - 28 Oct

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

Great Barrington

RM587

RM656 total

includes taxes & fees

2 Nov - 3 Nov

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.

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

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

South Lee

RM478

RM614 total

includes taxes & fees

13 Oct - 14 Oct

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

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.

A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

Hilton Garden Inn Lenox Pittsfield

Pittsfield

RM522

RM584 total

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

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

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

Element by Marriott Lenox Berkshires

Lenox

RM584

RM653 total

includes taxes & fees

8 Nov - 9 Nov

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 hotel building with the name "Hotel Downtown" on the facade.

A modern interior with a large window, a wooden table, and bar stools.

Hotel Downstreet, an Ascend Collection Hotel

North Adams

RM487

RM544 total

includes taxes & fees

1 Nov - 2 Nov

View all properties