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The best family hotels in The Berkshires

Check out our pick of great family hotels in The Berkshires

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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The Williams Inn has a fitness centre, shared lounge, a restaurant and bar in Williamstown. Located around 24 km from Bennington Battle Monument, the hotel with free WiFi is also 46 km away from Cranwell Spa & Golf Club. The accommodation offers a 24-hour front desk and a concierge service for guests. Super nice staff Very clean Large bedroom and bathroom Great breakfast

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9.4
Superb
173 reviews
Price from
US$239
per night

Located in Great Barrington, 19 km from Cranwell Spa & Golf Club, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires offers express check-in and check-out and free WiFi throughout the property. Boasting family rooms, this property also provides guests with a children's playground. The property is non-smoking and is set 12 km from Norman Rockwell Museum. Clean and comfortable. Very nice lobby

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9.2
Superb
100 reviews
Price from
US$143
per night

Located 14 miles from skiing on Jiminy Peak, this Williamstown motel is also 3 minutes’ drive from Williams College. Guests can enjoy a continental breakfast each morning and have access to free Wi-Fi. Very comfortable room and amazing breakfat with a lot of fresh season fruits.. People very nice and friendly.

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9
Superb
381 reviews
Price from
US$109
per night

Located in Hancock just 35 miles from Norman Rockwell Museum, this hotel features an indoor and outdoor pool. Tennis courts and a hot tub are located on site. A full kitchen is featured in all suites.

A game room complete with billiards offers recreational fun at Bentley Brook Wyndham. A picnic area featuring BBQ facilities is available. After a day of exploring, guests can relax in the sauna. of having a snow rink at my bedroom door

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9
Superb
299 reviews
Price from
US$129
per night

Nestled among the Berkshires, this 3 acre property boasts mountain views and free WiFi access. This Williamstown, Massachusetts motel is less than half a mile from Williams College.

Each guest room at the Maple Terrace Motel features cable TV with DVD player, a writing desk, and a refrigerator. A telephone and coffee-making facilities are also available. Beds were extremely comfortable - most important feature when traveling. Bravo!

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9.1
Superb
329 reviews
Price from
US$99
per night

Located on four acres, this bed and breakfast features traditional exteriors and stunning, updated designer rooms and bathrooms which are all equipped with cable TV, high-speed internet, and coffee machines. Many rooms feature fireplaces and private balconies. The Boston Symphony Orchestra's Tangle wood Institute is five minutes away, and the restaurants of Lenox are 1 minute away. The brownies were yummy and staff great!

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9
Superb
556 reviews
Price from
US$182.40
per night

Set in North Egremont, 18 km from Norman Rockwell Museum, Prospect Berkshires offers accommodation with free bikes, free private parking, an outdoor swimming pool and a garden. Among the various facilities are a terrace, a bar, as well as water sports facilities. Offering free WiFi throughout the property, the non-smoking hotel features a sauna and evening entertainment. Great swim in the lake! Beautiful hut, very relaxing.

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9.8
Exceptional
13 reviews
Price from
US$295
per night

Situated in Lenox, 2.4 km from Tanglewood Musical Center, Doctor Sax House features accommodation with a shared lounge, free private parking, a terrace and a restaurant. With a bar, the 4-star hotel has air-conditioned rooms with free WiFi, each with a private bathroom. The property is non-smoking and is located 2.4 km from Cranwell Spa & Golf Club. Lenox is one of the most inviting towns in the Berkshires and the beautifully restored Dr Sax House is a gem in its center. We arrived on the coldest day of winter to celebrate our wedding anniversary, but Brian and Kelly and their solicitous staff gave us the warmest welcome and most delightful stay we have had anywhere. I don't think we've ever encountered a bedroom and bathroom with so many thoughtful amenities: not just toiletries but everything you might have forgotten, not just a yoga mat but a gym bag filled with small weights and accessories. Their cozy restaurant Dulu is en suite with a beautifully appointed bar. The menu is imaginative and my baked halibut was the most delicious I have enjoyed - ever. With temperatures in the single digits it was a plus for us to be able to simply hang out at the Inn, but under balmier conditions all the artistic and culinary attractions that Lenox has to offer are right outside the door. It's also a perfect base for Tanglewood and many other local cultural activities. We look forward to our return soon!

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9
Superb
21 reviews
Price from
US$316.58
per night

Located in Sheffield, within 25 km of Norman Rockwell Museum and 31 km of Cranwell Spa & Golf Club, Wilder House Berkshires provides accommodation with a garden as well as free private parking for guests who drive. The property features garden views and is 32 km from Tanglewood Musical Center and 32 km from Tanglewood. Holley Williams House Museum is 23 km from the bed and breakfast and Haystack Mountain State Park is 23 km away. I will never forget this magical accommodation. I felt like I was in a fairy tale house. Great breakfast with homemade products that the owner Brad prepared himself.

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9.6
Exceptional
72 reviews
Price from
US$180
per night

2 Bed Berkshire Getaway minutes to Jiminy Peak Ski is situated in Hancock, 33 km from Tanglewood Musical Center, 33 km from Tanglewood, and 34 km from Cranwell Spa & Golf Club. The property is around 35 km from Rensselaer Polytechnic Institute, 37 km from Norman Rockwell Museum and 38 km from Albany-Rensselaer Amtrak. There is an outdoor fireplace and guests can make use of free WiFi and free private parking.

For guests with children, the apartment features outdoor play equipment. Guests at 2 Bed Berkshire Getaway minutes to Jiminy Peak Ski can enjoy skiing nearby, or make the most of the garden. Building is cute and easy to find. Parking was excellent being right in front of the door of this apartment. very clean, well stocked, modern space. Comfy living room for hanging out, large kitchen with everything you need to cook, a clean bathroom with soap, shampoo and toothbrushes and a big shower. It was cool I’m the house and easy to adjust the temperature. Location was good. Reasonably close to all the things we wanted to do, including Tanglewood, The Clark, Mass MoCA, the Mount, Lenox, Great Barrington, plus hiking, and skiing and horses next door! And a great cheese shop down the road (Four Fat Fowl).

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9.9
Exceptional
9 reviews
Price from
US$118.80
per night

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