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

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Check availability on The Berkshires Family friendly Hotels

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Our top choices for The Berkshires family-friendly hotels

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.

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

Lee

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

S$181

includes taxes & fees

14 Sept - 15 Sept

A room with a ping pong table, arcade games, and vending machines.

A serene riverside view with a stone bridge, reflecting trees and buildings.

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

South Lee

S$191

includes taxes & fees

31 Aug - 1 Sept

An indoor swimming pool with clear water, tiled floors, and a blue wall.

A modern cafe with seating areas, a coffee station, and large windows offering a view of greenery.

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.

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

Pittsfield

Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Centre.

S$169

includes taxes & fees

24 Sept - 25 Sept

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

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

4. 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$276

includes taxes & fees

31 Aug - 1 Sept

An outdoor patio area with multiple chairs and tables, surrounded by lush greenery and trees.

A sign with the word "CLARM" on a grassy field with a road and trees in the background.

A covered porch with beige siding, white railings, and a row of wooden benches.

A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.

5. Cozy Corner Motel

Williamstown

S$132

includes taxes & fees

9 Sept - 10 Sept

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

6. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.

S$162

includes taxes & fees

1 Sept - 2 Sept

A modern bar area with a central island, multiple bar stools, and a seating area with tables and chairs.

A Holiday Inn & Suites hotel with a modern design, featuring a prominent sign and a well-lit entrance.

A banquet hall with round tables set for a formal event, featuring white tablecloths, silverware, and floral centerpieces.

7. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.

S$169

includes taxes & fees

22 Sept - 23 Sept

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 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.

8. Element by Marriott Lenox Berkshires

Lenox

S$276

includes taxes & fees

31 Aug - 1 Sept

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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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

S$181

includes taxes & fees

14 Sept - 15 Sept

A multi-story hotel with balconies, a pond with rocks, and a clear sky.

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

Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

S$191

includes taxes & fees

31 Aug - 1 Sept

A snack bar with shelves of snacks and a refrigerated display.

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

Pittsfield

S$169

includes taxes & fees

24 Sept - 25 Sept

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$276

includes taxes & fees

31 Aug - 1 Sept

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

S$169

includes taxes & fees

22 Sept - 23 Sept

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

S$162

includes taxes & fees

1 Sept - 2 Sept

Element by Marriott Lenox Berkshires

Lenox

S$276

includes taxes & fees

31 Aug - 1 Sept

An outdoor seating area with Adirondack chairs and potted plants.

A hotel room with a large bed, two bedside lamps, a nightstand, a framed picture on the wall, and a window with curtains.

Cozy Corner Motel

Williamstown

S$132

includes taxes & fees

9 Sept - 10 Sept

A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

A living room with a patterned carpet, two sofas, a dining table, and chairs.

A circular pool with a tiled edge, surrounded by a concrete deck and a grassy area with chairs and a small shed.

Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

S$112

includes taxes & fees

1 Sept - 2 Sept

A garden with a swing set, a blue chair, and a flower bed.

A house with a porch, snow-covered ground, and a Christmas tree with lights.

A swimming pool with lounge chairs and a fence.

A garden with a wooden pergola, potted plants, and a lawn with chairs.

Maple Terrace Motel

Williamstown

S$177

includes taxes & fees

9 Sept - 10 Sept

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Family-friendly hotels with pools in The Berkshires

Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

S$191

includes taxes & fees

31 Aug - 1 Sept

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

Pittsfield

S$169

includes taxes & fees

24 Sept - 25 Sept