Best & Cheap Family Friendly Vacations in The Berkshires, MA

Compare family friendly vacation accommodation, From $35/night

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Best & Cheap Family Friendly Vacations in The Berkshires, MA: Top Deals

Beartown Forest Farmhouse -- 4 Minutes To Downtown Stockbridge
Guest Suite · 8 Guests · 4 Bedrooms
Beartown Forest Farmhouse -- 4 Minutes To Downtown Stockbridge
5.0 (1 review)
This guest suite is located in Beartown Forest Farmhouse, just 4 minutes away from downtown Stockbridge. It can accommodate up to 8 people and allows pets. Nearby popular restaurants include the Olde Heritage Tavern, The Red Lion Inn, and The Gypsy Apple Bistro & Bar. Popular activities in the area include visiting Tanglewood Music Center, kayaking on the Housatonic River, and skiing at Butternut Ski Area. Nature lovers can also enjoy hiking along trails such as Bash Bish Falls Trail and Monument Mountain Trail.
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$419 /night*
Gorgeous Foliage - Modern House on 40 Acres --Clean, Private, Great for Families
Guest Suite · 2 Guests · 4 Bedrooms
Gorgeous Foliage - Modern House on 40 Acres --Clean, Private, Great for Families
4.7 (6 reviews)
This luxurious Guest Suite is located on 40 acres of gorgeous foliage and offers a modern house with private, clean accommodations for up to two people. It is located near many popular restaurants, activities, and trails such as the Bash Bish Falls State Park, Catamount Ski Area, Monument Mountain, The Red Lion Inn, and Mission Bar & Tapas.
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$1152 /night*
Berkshire Escape to Ski and Fish and Skate
Guest Suite · 6 Guests · 3 Bedrooms
Berkshire Escape to Ski and Fish and Skate
4.7 (6 reviews)
This Berkshire Escape to Ski and Fish and Skate is a perfect place for adventurers looking for outdoor activities. It can sleep up to 6 people and is pet-friendly. Located near the beautiful Berkshires, it offers easy access to popular attractions such as Butternut Ski Area, Jiminy Peak Mountain Resort, and The Bousquet Ski Area. Other nearby activities include fishing in the Hoosic River, hiking in Pittsfield State Forest, and skateboarding at Onota Lake Park. Popular restaurants in the area include Ninety Nine Restaurant & Pub, Ramunto's Brick & Brew Pizzeria, and Papa Gino's.
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$521 /night*
Hip Renovated Mid Century 4 Bedroom on Long Bow Lake
Guest Suite · 6 Guests · 4 Bedrooms
Hip Renovated Mid Century 4 Bedroom on Long Bow Lake
This Guest Suite is a hip and renovated mid-century 4 bedroom located on Long Bow Lake. It can sleep up to 6 people and does not allow pets. Nearby popular attractions include the Berkshire East Ski Resort, Zoar Outdoor Adventure Center, and The Bounti-Fare Restaurant & Lounge. There are also plenty of trails for hiking and biking in the area.
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$492 /night*
Wild Berkshires Ranch is located in a private wooded lot with Expansive Yards!
Guest Suite · 2 Guests · 4 Bedrooms
Wild Berkshires Ranch is located in a private wooded lot with Expansive Yards!
4.9 (50 reviews)
This Guest Suite is a perfect getaway located in the Wild Berkshires Ranch with expansive yards and private wooded lot. It can sleep up to two people and allows pets for an additional fee. Popular nearby restaurants include The Old Forge Restaurant, Canyon View Farm Market & Cafe, and Bizen Japanese Cuisine. Activities close by include hiking trails at October Mountain State Forest and Tanglewood Music Center for concerts and cultural events.
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$453 /night*
Ashintully Cottage in spectacular setting
Cottage · 7 Guests · 4 Bedrooms
Ashintully Cottage in spectacular setting
5.0 (7 reviews)
This charming Ashintully Cottage is located in a spectacular setting with easy access to popular attractions, restaurants, and trails. Nearby activities include the Norman Rockwell Museum, Ski Butternut, and the Berkshire Theatre Group. Popular nearby restaurants include Mezze Bistro + Bar, Gedney Farm, and Allium Restaurant & Bar. For outdoor recreation, visitors can take advantage of miles of hiking trails at Tanglewood Nature Center or enjoy kayaking along Stockbridge Bowl.
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$415 /night*
Econo Lodge Lee - Great Barrington
Hotel
Econo Lodge Lee - Great Barrington
3.4 (227 reviews)
This Hotel, Econo Lodge Lee - Great Barrington, located in Lee, allows pets and is near popular restaurants such as The Old Mill and The Log Cabin, activities like Naumkeag, a historic house and garden, and trails including the Appalachian Trail and the Lenox Mountain Trail.
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$53.59 /night
Holiday Inn Club Vacations Oak N' Spruce Resort
Hotel
Holiday Inn Club Vacations Oak N' Spruce Resort
This Holiday Inn Club Vacations Oak N' Spruce Resort is a pet-friendly hotel located in the scenic Berkshire Mountains of Massachusetts. Guests staying at this resort can enjoy nearby activities such as skiing, snowshoeing, and horseback riding at Jiminy Peak Mountain Resort or explore the trails at October Mountain State Forest. Popular restaurants in the area include The Red Lion Inn, Trattoria La Famiglia, and Beech Tree Grill & Bar.
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$119 /night
Quality Inn
Motel
Quality Inn
4.0 (334 reviews)
This Quality Inn is the perfect spot for a getaway. It is pet-friendly and offers easy access to popular local restaurants like The Local, California Pizza Kitchen, and Olive Garden, as well as nearby activities such as hiking trails at Prospect Mountain, kayaking on Lake George, and skiing at Gore Mountain.
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$84.15 /night
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How Does The Vacation Home Rental Price Look Like in The Berkshires, MA?
Vacation House & Cottage Rental Price Information in The Berkshires, MA
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The graph shows the percentages of vacation homes in each price bucket. The Berkshires has the largest percentage (17.14%) of homes in $500+ price range.
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How Many Rental Accommodations Are Pets Friendly in The Berkshires, MA?
Pets Allowed vs Not Allowed in The Berkshires, MA
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37.08% of vacation homes in The Berkshires are pet friendly. Either you bring your loved pets on vacation or you have pet allergies, make sure to select the homes by applying the right filters.
Where can we find the best family-friendly restaurants in The Berkshires, MA?
Family-Friendly Restaurants in The Berkshires, MA
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The Berkshires is home to some of the best family-friendly restaurants in Massachusetts. From cozy cafes to classic diners, you'll find something for everyone in your family. Here are three popular restaurants you should try when visiting The Berkshires.

  • Baba Louie's Pizza: Enjoy a slice of pizza with the whole family at Baba Louie's. This restaurant offers creative and delicious pizzas made with fresh ingredients. With its friendly atmosphere, it's a great place for families.
  • Berkshire Mountain Bakery: This bakery specializes in artisanal breads and pastries. It also serves breakfast and lunch dishes that are sure to please even the pickiest eaters. The rustic atmosphere makes it a great spot for family gatherings.
  • Chez Nous Bistro: If you're looking for a more upscale dining experience, Chez Nous is the perfect option. This French bistro offers an extensive menu featuring classic French dishes as well as seasonal American cuisine. Kids will love the homemade desserts!
What activities can we do with the family in The Berkshires, MA?
Family-Friendly Activities in The Berkshires, MA
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The Berkshires offer a variety of fun activities for families to enjoy. Whether you want to explore nature or visit interesting attractions, there's something for everyone. Here are three family-friendly activities that you should check out during your stay.

  • Naumkeag: Take the kids to this historic estate to learn about its fascinating history. The sprawling grounds feature gardens, ponds, and breathtaking views of the surrounding mountains. The house itself has been restored to its original 19th century grandeur.
  • Hancock Shaker Village: Discover the unique culture of the Shakers at this living museum. Take a guided tour of the village to learn about the lifestyle of the Shakers and their contributions to early American industry. There are plenty of hands-on activities for the kids as well.
  • Berkshire Scenic Railway Museum: Take a ride on a vintage train for a fun day out with the family. Enjoy a scenic journey through the Berkshire countryside while learning about the area's rich history. You can also take part in special events like story time or holiday celebrations.
What Are The Must-Visit Places in The Berkshires, MA?
Top Rated Places to Visit in The Berkshires, MA
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