Top 10 Family Resorts In Berkshires, Massachusetts - Updated 2024

Malavika
Malavika 
Contributing Writer
Updated
| 6 min read

There are few regions in New England as bucolic as the Berkshires. Boasting fantastic local cuisine, architecture, and the great outdoors, the region makes for an excellent destination for family fun. Go trampolining and rock climbing with kids at Jiminy Peak Mountain Resort. Explore the culture of the region at Norman Rockwell Museum, which has a great scavenger hunt for families! Does your family enjoy horseback riding? Berkshire Horseworks offers some excellent unique experiences of riding horses, amongst others. Likewise, family-friendly inns and luxury hotels in the Berkshires region are abundant, and across every price range. Not only do they offer proximity to beaches and attractions, but they also offer the convenience of swimming pools and restaurants so that there’s something for everyone to do, including kids. To that end, here are the top family resorts in Berkshires, Massachusetts.

We handpicked these listings carefully, considering (wherever possible) recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to family-friendly amenities and activities. The image galleries get refreshed with the latest updates regularly. They were last updated on May 23, 2024.

1. The Ponds at Foxhollow by Capital Vacations, Lenox (from USD 125)

A whole lot of family fun at the excellent Ponds at Foxhollow begins right at the sprawling resort itself. For instance, go hiking or cross-country skiing on the grounds or take a boat out on the winding pond. Choose from a host of indoor and outdoor pools where both adults and children can indulge in water fun. Watch movies together, ride bikes, play games - the opportunities are endless.

The one/two-bedroom cottages are all spacious, complete with views of the pond, dining areas, and full kitchens to whip up meals. End your wonderful day around the barbecue and enjoy an alfresco dinner under the stars. The best bit? The Ponds at Fox Hollow boasts a magnificent library too!

Stayed at this property?

The Ponds at Foxhollow by Capital Vacations

Wifi Available

Address: 3 Foxhollow Drive
25.8 km (16.1 mi) from Jiminy Peak Mountain Resort

Parking Tennis court Sauna Fitness centre Golf course (within 3 km) Garden Terrace Non-smoking rooms

2. Eastover Estate and Eco Village, Lenox (from USD 545)

The Eastover Estate and Eco Village looks less like a resort and more like a huge mansion rising out of the gorgeous landscape. Tucked right in the heart of Lenox, this fantastic family resort is set amidst beautiful and lush gardens that your children will absolutely love.

Go on hiking tours during the day. Take yoga, qi-gong, and tai-chi classes on weekends with your entire family. Even the entertainment venue of Tanglewood Musical Center is merely five minutes from the resort. The best of them all is the indoor pool, where you can have water fun around the year the weather notwithstanding. All rooms at this eco estate come with small fridges, plush beds, and equally well-designed bathrooms. Huge windows and patios look out over the lovely property.

Stayed at this property?

Eastover Estate and Eco Village

Wifi Available

Address: 430 East Street, Box 2282
20.71 km (12.9 mi) from Jiminy Peak Mountain Resort

Parking Meeting/banquet facilities Garden Terrace Non-smoking rooms Free parking Internet services Safety deposit box

3. Jiminy Peak Mountain Resort, Hancock (from USD 163)

There’s no ski resort in the Berkshires more popular than Jiminy Peak Mountain Resort, which has an endless array of entertaining activities for everyone. Not only do they have a children’s playground, a ski school, and amazing pools, but you’ll also find thrilling adventure parks.

If you’re a large family, choose the Country Inn suites or the two/three-bedroom mountainside vacation homes or apartments. All of them come with balconies, tons of space, kitchenettes, and comfy bedrooms. Your kids can play games in the game room, even as you work out in the fitness center. Relax with a massage at the spa before proceeding to the outdoor heated swimming pool for some family fun time. Moreover, the on-site restaurant serves delicious American fare that your kids will love.

Stayed at this property?

Jiminy Peak Mountain Resort

Wifi Available

Address: 37 Corey Road
344 meters (0.3 ft) from Jiminy Peak Mountain Resort

Parking Restaurant Meeting/banquet facilities Bar 24-HOUR FRONT DESK Tennis court Fitness centre Golf course (within 3 km)

Other family accommodations

4. Apple Tree Inn, Lenox (from USD 154)

Located a hop, skip, and jump from Tanglewood Musical Center, Apple Tree Inn is an excellent and serene family-friendly property. Begin your day with a delicious continental breakfast in the garden or the sunroom, depending on the season. Besides the neighborhood being popular with cycling, you can even play tennis on the property. The family rooms are spacious and they even come with terraces. Free Wi-Fi, large bathrooms, and cloud-like beds make up the rest of the rooms.

Stayed at this property?

Apple Tree Inn

Wifi Available

Address: 10 Richmond Mountain Road
22.58 km (14.1 mi) from Jiminy Peak Mountain Resort

Parking Restaurant Meeting/banquet facilities Bar 24-HOUR FRONT DESK Golf course (within 3 km) Garden Terrace

5. 1896 House Country Inn - Brookside & Pondside, Williamstown (from USD 110)

Families with older children will love the 1896 House Country Inn, a bucolic yet lavish accommodation that’s set amidst acres of lush landscaping in the heart of Williamstown. Despite being an inn, the zenith of relaxation on this property is the outdoor heated pool, which overlooks the lush Massachusetts foliage.

Dig into hearty New England fare at the on-site restaurant and sip delicious craft cocktails at the bar. In fact, your day begins with a hearty breakfast of oatmeal, yogurt, waffles, bacon, eggs, and more. You’ll love the country-styled rooms here too, complete with four-poster beds and pinewood walls. Modern touches in the form of coffeemakers, fridges, and flatscreen TVs will make your stay comfortable.

Stayed at this property?

The 1896 House Country Inn - Brookside & Pondside

Wifi Available Wheelchair accessible

Address: 910 Cold Spring Road
16.23 km (10.1 mi) from Jiminy Peak Mountain Resort

Parking Restaurant Pets allowed Room service Meeting/banquet facilities Bar Tennis court Golf course (within 3 km)

6. Tourists, North Adams (from USD 473)

Rustic-chic gets a new definition at Tourists, a superb mountain resort in the heart of North Adams. After a day of hiking and skiing, a dip in the divine outdoor pool sounds just right. Peppered with sun loungers, the deck overlooks the gorgeous gardens around, making it a great place to unwind. The restaurant offers classic American fare, while the bar is a great place to enjoy a nightcap before retiring.

During the summer months, the sun terrace is the perfect place to sunbathe while listening to music or reading a good book. Besides free Wi-Fi, all rooms here come with views of either the garden or the pool. Done up in neutral hues, you also get flatscreen TVs and swish bathrooms for a wonderful stay.

Stayed at this property?

Tourists

Wifi Available Wheelchair accessible

Address: 915 State Road
19.03 km (11.9 mi) from Jiminy Peak Mountain Resort

Parking Restaurant Pets allowed Room service Bar 24-HOUR FRONT DESK Garden Terrace

7. The Porches Inn at Mass MoCA, North Adams (from USD 227)

Yet another family favorite in the northern part of the Berkshires is the Porches Inn. Offering a delicious complimentary continental breakfast and a heated outdoor pool, it’s one of the best small family hotels in the Berkshires.

Have a wonderful time playing games with your family in the parlor and explore the exquisite Massachusetts Museum of Contemporary Art (a.k.a. Mass MoCA), which the inn overlooks. Work out in the fitness center and soak your stresses in the hot tub. Gather around the fire pit for a grilling alfresco dinner. With just 47 rooms, staying here is as intimate as it gets. Families will love the two-bedroom split-level suite, with each bathroom featuring a hot tub-style tub.

Stayed at this property?

The Porches Inn at Mass MoCA

Wifi Available

Address: 231 River Street.
21.7 km (13.5 mi) from Jiminy Peak Mountain Resort

Parking Pets allowed Room service Meeting/banquet facilities Bar 24-HOUR FRONT DESK Golf course (within 3 km) Garden

8. Club Wyndham Bentley Brook, Hancock (from USD 87)

Another excellent family resort in the Berkshires is Wyndham Bentley Brook, an all-season destination that’s perfect for a skiing vacation at the Jiminy Peak Mountains. It’s an excellent place during summer when the entire family can hike across the mountain trails.

The resort itself offers a host of things to do, especially the two swimming pools for a refreshing dip. Besides the fitness center, you’ll love the sauna for relaxing the muscles. Plus, the tennis courts are great for fans of the sport. Do you have younger kids? They’ll love the games room and the barbeque facilities. All suites are modern, with dining rooms, plush bedrooms, and immaculate bathrooms.

Stayed at this property?

Club Wyndham Bentley Brook

Wifi Available

Address: 1 Corey Road
169 meters (0.2 ft) from Jiminy Peak Mountain Resort

Parking Tennis court Sauna Fitness centre Non-smoking rooms Laundry Facilities for disabled guests Skiing

9. The Red Lion Inn, Stockbridge (from USD 278)

Families with older children will love the elegance and tranquillity at the Red Lion Inn, which has not one or two but five restaurants to choose from. Choose from 82 unique rooms at the 1773-built inn, which features 19th-century antique furniture, floral upholstery, and chic bathrooms.

Aside from the rooms, there are also private guesthouses across the lush property. The rest of the inn is equally excellent, complete with a heated outdoor pool, on-site massage services, and a birdcage-inspired luft. Oh, and cat lovers will love Norman, the inn’s resident feline famously named after Stockbridge’s most famous denizen, Norman Rockwell.

Stayed at this property?

The Red Lion Inn

Wifi Available

Address: 30 Main Street
30.49 km (19.0 mi) from Jiminy Peak Mountain Resort

Parking Restaurant Pets allowed Meeting/banquet facilities Bar 24-HOUR FRONT DESK Fitness centre Golf course (within 3 km)

10. Holiday Inn Club Vacations Oak n' Spruce Resort, South Lee (from USD 189)

Are you looking for a value-for-money family resort in the Berkshires? Then head straight to Holiday Inn Club Vacations Oak n’ Spruce Resort, your ticket to a wallet-friendly Berkshires getaway. Choose from two indoor and outdoor pools, each for an entire day of water fun at the resort.

Post your swim, enjoy a soak in the hot tub or work out in the fitness center. Enjoy a spot of mini-golf or a session in the game room and an alfresco dinner around the barbeque grill in the evening. You have the choice of a host of condo-style rooms, all with balconies and well-equipped kitchens for whipping up meals.

Stayed at this property?

Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires an IHG Hotel

Wifi Available Wheelchair accessible

Address: 190 Meadow Street
31.36 km (19.5 mi) from Jiminy Peak Mountain Resort

Parking Bar Tennis court Fitness centre Non-smoking rooms Business centre Laundry Facilities for disabled guests

A fun-filled family vacation in the Berkshires

The Berkshires offer well-rounded family fun, whether you want to stay indoors and enjoy the weather or get out and hike, play sports, or go skiing. In addition to lakefront rentals and Airbnb vacation rentals in the Berkshires, there are also these family-friendly hotels and inns with excellent accommodations and amenities. They also have added advantage of being close to great attractions and sights in the region. So, choose one of these family resorts in Berkshires, Massachusetts, for a memorable vacation.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Malavika, a freelance writer and coffee enthusiast, is well-versed in Kopfkino. Her interests include engaging discussions on New Zealand, the domino theory, dystopian fiction, and Harry Potter.

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