TOP Family Friendly Hotels in The Berkshires for 2026 - 𝗙𝗿𝗲𝗲 𝗖𝗮𝗻𝗰𝗲𝗹𝗹𝗮𝘁𝗶𝗼𝗻 on Select Hotels

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.

S$152

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

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.

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

Lee

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

S$169

includes taxes & fees

10 Nov - 11 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.

3. 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 Scrabble game on a wooden table with a vase of flowers and a cup.

A cozy library with bookshelves, a fireplace, and comfortable seating.

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

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

4. Berkshires Untold

Lenox

S$186

includes taxes & fees

1 Nov - 2 Nov

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 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.

5. 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 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.

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

6. 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

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

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.

A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.

7. Hotel On North

Pittsfield

S$192

includes taxes & fees

1 Nov - 2 Nov

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

8. 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

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

S$152

includes taxes & fees

1 Nov - 2 Nov

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

S$169

includes taxes & fees

10 Nov - 11 Nov

Courtyard by Marriott Lenox Berkshires

Lenox

S$180

includes taxes & fees

1 Nov - 2 Nov

A coffee station with two coffee machines and a variety of coffee pods and cups.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

S$119

includes taxes & fees

10 Nov - 11 Nov

The Cornell Inn, Lenox & The Berkshires

Lenox

S$225

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.

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

S$205

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 café with a display case, a frozen food section, and a marketplace sign.

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

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

South Lee

S$192

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 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.

A hotel patio with outdoor seating and a fire pit.

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

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.

Element by Marriott Lenox Berkshires

Lenox

S$205

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

A modern cafe with a wooden accent wall, a coffee machine, and black chairs.

A reception area with a large landscape painting, a dark reception desk, and a potted plant.

Hotel Downstreet, an Ascend Collection Hotel

North Adams

S$171

includes taxes & fees

1 Nov - 2 Nov

View all properties