Are you searching for the perfect winter vacation in the Berkshires for your family?
Whether you’re dreaming of hitting the slopes or exploring cultural gems like theย Norman Rockwell Museum, finding the rightย luxury resortย in the Berkshires that keeps you and your kids happy is essential.
These family-friendly Berkshires Luxury Resorts offer a mix of relaxation, adventure, and funโperfect for a winter escape.
Youโll enjoy the high-end amenities, while the kids will love the activities designed just for them. Letโs explore your options.
Explore the Top Berkshires Luxury Resorts for Families
The Red Lion Inn
Stockbridge, MA
Winter at the Red Lion Inn in Stockbridge, MA.
Theย Red Lion Innย is a historicย New Englandย gem in downtown Stockbridge that offers more than just charm โ itโs packed with family-friendly features to make your winter stay both comfortable and fun.
Highlights for Families
- Heatedย Outdoor Poolย andย Hot Tub: Open year-round, even during the winter months, so your kids can enjoy a swim even under the falling snow.
- On-Site Dining with Kidsโ Menus:ย Theย Red Lion Innย offers multipleย dining options, so even the pickiest eaters will find something they love.
- Babysitting Services:ย Take time to unwind while knowing the kids are in good hands (upon availability).
- Nearby Attractions:ย Aย short driveย to theย Norman Rockwell Museum,ย Berkshire Botanical Garden, and Stockbridge Library and Museum, giving families plenty to explore.
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The Red Lion Inn isnโt the only place where you can soak in the scenery…check out this list of hotels with outdoor winter swimming pools. You can be swimming under the snowflakes all winter. ย
Guest Rooms at The Red Lion Inn
Theย guest roomsย at Theย Red Lion Innย blend historic elegance with modern luxury.
Families can enjoy spacious suites with plush bedding, upscale furnishings, and thoughtful amenities like gas fireplaces and pull-out sofas, creating the perfect relaxation space after exploring the Berkshires.
Why Stay at Theย Red Lion Inn
Theย Red Lion Innย balances 250 years of historic charm with modern comforts, making it one of theย best hotelsย for families looking to experience classicย New Englandย hospitality while staying near some of Berkshire’s top winter attractions.
Winter rates start as low as $149/night. (discounts can be found directly on Red Lion Inn’s Website or Booking.com)
The Williams Inn
Williamstown, MA
Cozy up with a board game at The Williams Inn (Photo Credit: The Williams Inn)
Theย Williams Innย offers modern elegance and a prime location, making it a great choice for families who wantย easy accessย to both winter sports andย cultural experiencesย in the Berkshires.
Highlights for Families
- Interconnected Rooms:ย Spacious rooms allow families to stay connected while enjoying a little privacy.
- Reading Nook with Board Games:ย Perfect for family game nights or a cozy break.
- Close toย Ski Resorts:ย Hit the slopes easily, as topย ski resortsย Jiminy Peak Mountain Resort and Berkshire East Mountain Resort are just aย short driveย away.
- Nearby Cultural Sites:ย Take the kids to theย Clark Art Instituteย for a mix of learning and fun.
Guest Rooms at The Williams Inn
The guest rooms at The Williams Inn feel like a warm hug from the Berkshiresโthink modern farmhouse charm with cozy touches that make you want to curl up with a good book (or at least pretend you have time to).
Why Stay at The Williams Inn
The Williams Inn blends New England charm with modern comforts. It offers stylish, cozy rooms, a welcoming tavern, and a prime location in the heart of the Berkshires.
Plus, the reading nook with board games makes for cozy spot to unwind after a day of adventure.
Winter rates start at $229/night.
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Need ideas for winter escapes in Massachusetts that don’t involve skiing?
From unique museums to winter adventures, our Massachusetts winter getawayย guide has plenty of inspiration.
TOURISTS Berkshires
North Adams, MA
Enjoy a luxe retreat with a natural vibe at TOURISTS Berkshires. (Photo Credit: TOURISTS Berkshires)
TOURISTS Berkshires inย North Adamsย is a nature-focused retreat that blends outdoor adventure with high-end comfort.
Your family can enjoy a wide range of ever-changing daily activities, such as hikes, scavenger hunts, art classes, and yoga, making it aย great placeย for those seeking an active yet relaxing winter getaway.
Highlights for Families
- Art & Adventure Classes: These on-site classes, many of which are included in your stay, are designed to entertain and engage kids of all ages.
- Free Sโmores: Gather around the fire pit for nightly sโmores, a family favorite.
- Outdoor Fun:ย Enjoy access to scenicย nature trailsย and winter hikes. Take your family on a walk across the suspension bridge over the Hoosic River, where you can look down at the icy water below.
- Fire Pits: End your day by the outdoor fire pitsโthereโs plenty to keep everyone entertained during the colder months.
- Sing for Your Slumber:ย Live music performed by talented touring musicians.
Guest Rooms at TOURISTS Berkshires
The rooms at TOURISTS are minimalist yet luxurious, offering cozy bedding, heated floors, and warm, natural tones.
Families appreciate the comfortable, spacious design that blends simplicity with modern amenities for a relaxing stay in the Berkshires.
Why Stay at TOURISTS Berkshires
This luxury retreat immerses families in nature, offering unique experiences through art and adventure activities. Cozy evenings with free sโmores and outdoor winter fun make it an ideal spot for creating lasting family memories in the Berkshires.
Winter rates start at $299/night.
The Kemble
Lenox, MA
Bright and cozy bedroom at The Kemble (Photo thanks to The Kemble)
The Kemble in Lenox is the perfect fit if youโre looking for a private luxury retreat where your family can own the whole property.
With 13 bedrooms and the ability to sleep up to 35 guests, this exclusive private estate combines historic charm with modern luxury, offering a personalized luxury experience for families in the Berkshires.
Highlights for Families
- Entire Estate Rental: Enjoy complete privacy and exclusive access to the propertyโs 3 acres while just a short drive from downtown Lenoxโperfect for family reunions or special gatherings.
- Entertainment for All Ages:ย The Kemble Estate includes a VR gaming room, PlayStation gaming, retro arcade, ping pong, board games, and more.
- Outdoor Activities: Bocce, croquet, kayaking, paddleboarding, and more are available (seasonally) on the property.
- Proximity toย Cultural Activities:ย Located near Tanglewood, theย Norman Rockwell Museum, and other popular Berkshireย cultural attractions.
The Kemble has plenty of seats for the whole family to dine together. (Photo thanks to The Kemble)
Guest Rooms at The Kemble
The Kemble in Lenox is perfect for a multi-family getaway. With 13 spacious guest rooms that sleep up to 35, thereโs room for everyone to spread out.
Many rooms feature a mix of king, queen, and even twin bedsโideal for families with younger kids.
Itโs super convenient for families traveling together, especially since there are large common spaces where everyone can hang out, share meals, and unwind.
The flexible room setups make it great for big groups, whether youโre planning a family reunion or want to enjoy a weekend escape with friends.ย
Why Stay at The Kemble
The Kemble Estate in the Berkshires offers a unique blend of historic charm and modern luxury, giving your family the privacy of an exclusive estate with all the amenities you could wish for.
With a variety of activities for both kids and adults, it delivers a more personalized experience than a 5-star hotel, making it the perfect choice for larger family gatherings in the heart of the Berkshires.
Rates start at $2495/night plus fees.
Wellspring Luxury Rental
West Stockbridge, MA
Enjoy your own indoor private pool at Wellspring (Photo thanks to Wellspring @ Avantstay)
Wellspring luxury rental offers the ultimate family-friendly retreat with its indoor poolโa rare find for winter getaways in the Berkshires.
This modern property managed by AvantStay combines luxury and comfort, making it perfect for families looking to enjoy the Berkshires.
Whether you’re relaxing next to the indoor pool or exploring the nearby trails, Wellspring has something for everyone.
Family Highlights
Indoor Pool: The standout feature is the private indoor pool, a game-changer for families looking to keep the kids entertained no matter the weather. (pool heat is extra $)
Room for Everyone: With 7 spacious bedrooms that sleep up to 12 guests and multiple living areas, there’s plenty of space for large families or groups traveling together.
Outdoor Fun: Beyond the pool, families can relax on the large patio or warm up in the hot tub after a day of winter adventures.
Guest Rooms at Wellspring
Wellspringโs 7ย beautifully designed guest rooms offer a mix of king and queen beds, providing plenty of room for everyone to relax.
Each room has a cozy, modern feel, and the large windows let in natural light, making the space feel bright and welcoming even on chilly winter days.
There is plenty of closet space and thoughtful touches to make your stay even more comfortable.
Why Stay at Wellspring
Wellspring is ideal for families looking for a luxurious winter escape, with the indoor pool as a game-changer.
The property requires a 2-night minimum stay, with prices starting at $950/night plus tax and a cleaning fee.
Things to Do in the Berkshires This Winter
The Berkshires in Massachusetts are known for their winter activities.
Beyond the luxury resorts, the Berkshires offer endless ways to entertain your family this winter.
Spend the day skiing or snowboarding on nearby slopes, exploring local museums, or catching live entertainment in a charming small town.
Whether you’re looking for adventure or something more low-key, the Berkshires have everything you need to make your familyโs winter getaway unforgettable.
If you’re looking for more winter inspiration beyond the Berkshires, check out my guide to Winter New England Family Getaways. Itโs packed with fun destinations that will help you plan an unforgettable family escape this winter!
Hit the Ski Slopes in the Berkshires
Skiers and snowboarders of all levels will enjoy the Berkshire Mountains.
Explore Cultural Attractions in the Berkshires This Winter
The Clark Art Institute in Williamstown, MA (Photo Credit: Museumclark)
Outdoor Winter Adventures in the Berkshires
From active adventures to a quiet walk through the woods, the Berkshires have it all.
- Snowshoeing and Cross-Country Skiing:
- Clark Art Institute:ย Enjoy free family snowshoeing on the scenic winter trails.
- Canterbury Farms:ย Explore 13 miles of groomed trails. Trail fees are $20 for adults and $15 for children. Equipment rentals are $25 for adults and $20 for kids.
- Notchview Reservation:ย Discover 25 miles of groomed trails in theย Berkshire Hills. Open Thursday through Tuesday, 8 AM to 4 PM. Trail fees are $20 for adults and $10 for children. Rentals are $20 for adults and $15 for kids.
- Ice Skating:ย Outdoor rinks in the Berkshires, including those at Canterbury Farms and local parks, provide charming locations for families to skate together.
- NightWood Experience:ย NightWood is an immersive outdoor sound and light experience in Lenox, set against Edith Whartonโs historic home. This 3/4-mile illuminated path through the woods and gardens offers a magical experience set to music that sparks wonder and imagination for all ages.
- Winter Horseback Riding:ย Blue Rider Stables in Great Barrington offers year-round trail rides. During the winter, your family can enjoy riding through snow-covered trails and past a Christmas tree farm, making for a festive and memorable outing.
Relax and Recharge in the Berkshires This Winter
Cozy up in the Berkshires with your family this winter.
- Spa Treatments: Luxury spa resorts like Miraval Berkshires and Canyon Ranch Lenox are the perfect places to recharge. Indulge in massages, facials, or other treatments while the kids enjoy their own activities.ย
- Fire Pits and Cozy Common Areas:ย Many resorts, including The Red Lion Inn and The Kemble, feature inviting outdoor fire pits and cozy lounges.ย
Experience the Best Berkshires Luxury Resorts this Winter
These luxury resorts in the Berkshires are designed with families in mind and offer the perfect blend of relaxation and adventure. From excitingย New Englandย ski resortsย like Jiminy Peak and Bousquet Mountain toย cultural attractionsย at theย Clark Art Institute, thereโs something for everyone to enjoy.
After a day of outdoor winter excitement, you can unwind at world-class spas, gather around cozy fire pits, or simply relax by a crackling fireplace in your resortโs comfortable lounges.
Whether you’re seeking an adrenaline-packed day on the slopes or a tranquil retreat surrounded by nature, the Berkshires has it all.
Book your western Massachusetts getaway today and create lasting memories with your loved ones in this picturesque destination. With its stunning scenery, rich history, and unmatched hospitality, the Berkshires will become a cherished family tradition for years to come.
