TOP Family Friendly Hotels in Great Barrington for 2026 - 𝗙𝗿𝗲𝗲 𝗖𝗮𝗻𝗰𝗲𝗹𝗹𝗮𝘁𝗶𝗼𝗻 on Select Hotels

A large stone church with a tall bell tower and arched windows.

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Our top choices for Great Barrington family-friendly hotels

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

1. 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'.

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

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.

2. 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 hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

A bathroom with a white tiled floor, a wooden vanity with drawers, a white toilet, a bathtub, and a shower with a handheld showerhead.

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.

3. Monument Mountain Motel

Great Barrington

S$86

includes taxes & fees

1 Nov - 2 Nov

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

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

A modern bathroom with a white sink, a toilet, and a bathtub.

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

4. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Escape with the kids to this quiet, comfortable motel where family stays come with free beds and cots in immaculately clean rooms.

S$113

includes taxes & fees

13 Oct - 14 Oct

A large house with a balcony and a grassy yard.

A two-story building with a gabled roof and a chimney.

A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

A bathroom with a toilet, a shower with glass doors, and a towel rack with towels.

5. The Little Lion

Great Barrington

S$148

includes taxes & fees

18 Oct - 19 Oct

A modern bathroom with a white sink, black faucet, and a round mirror.

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

A grassy outdoor area with four blue Adirondack chairs arranged in a circle.

6. East Rock Inn

Great Barrington

S$178

includes taxes & fees

12 Nov - 13 Nov

A dining area with round tables set for two, a fireplace, and a mural on the wall.

A white two-story house with a front door, windows, and a chimney.

A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.

A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

7. The Old Inn On The Green

Great Barrington

S$448

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

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.

8. 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

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Choose what matters most at family-friendly hotels in Great Barrington

Breakfast included

Pool

All-inclusive

4 stars

5 stars

Top Great Barrington Hotel Reviews

Quality Inn Great Barrington

8/10 Good

"First, this is an absolutely gorgeous place! The outside areas are beautiful with comfy furniture, flowers and fire pits. Inside is a small intimate restaurant and bar, plus sitting area. With books and plants, very nice. We had dinner there which was excellent, and loved cocktails and sunset outside by the fire pits. When we checked in, we were assigned one of their premium rooms, which sounded great. However, it was on the second floor, at the very end of a long outside corridor, accessible only by stairs near the lobby. There is no elevator. We did go to the room, lugging our bags and a cooler. Unpleasant, as we are somewhat older. We concluded that we did not want to be that far from the main area, so asked to be moved, and were accommodated. We found the new room the same, but lacking a luggage rack and a coffee service (those were only available in the premium rooms at the end of the long corridor). We were given a luggage rack, and complimentary coffee was available in the restaurant in the morning, but it seemed odd that those were considered premium in such a nice place. Otherwise we loved the hotel, room was very nice with a comfortable bed and a very updated bath with a walk in shower. The real star of the hotel is the lobby restaurant and outdoor space - that was just perfect!"

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent

"Excellent room! Clean and good breakfast!"

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"Clean room, very friendly and accommodating staff and free parking"

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!"

The Little Lion

10/10 Excellent

"Simple place. Darling."

Travelodge by Wyndham Great Barrington Berkshires

10/10 Excellent

"The owners and staff are very helpful. The rooms are comfortable and clean."

Frequently asked questions

What's Great Barrington like for family-friendly holidays?

If you've been thinking about a holiday with your children, Great Barrington is a good choice. The entertainment, cafes and hiking trails are just a few things that make this an attractive spot for a family holiday. Arrange a flight into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 16.2 mi (26.1 km) from the city centre.

What's the best family accommodation in Great Barrington?

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires is a hotel with an indoor pool and free parking, and it's a top choice on Expedia for families. Travelodge by Wyndham Great Barrington Berkshires is another choice for your stay with the kids.

When's the best time to book a family-friendly holiday in Great Barrington?

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 -2°C. The snowiest months in Great Barrington 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 Great Barrington?

While you are visiting Great Barrington, you may want to round up the youngsters and make time to see interesting attractions such as Ski Butternut and Catamount Ski Area. Make sure that you have lots of time for activities such as Art et Industrie and Naumkeag Museum.

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Check availability on Great Barrington Family friendly Hotels

Our top choices for Great Barrington family-friendly hotels

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