Townhome holiday rentals in Berkshire County

Walk to college; 20 min to skiing Jiminy Peak

Travelling with a larger group up to 10-11? Rent the adjacent townhouse to sleep a total of 10-11 guests comfortably. Quiet, comfortable fully townhome w/tranquil nature/bike path a 3 min walk down the quiet street. Walk to: Williams College/restaurants The Clark North Adams Mass MOCA 20 min: Jiminy Peak (skiing and summer park) Ramblewood Adventure park Zipline Lakes (rent boats, fish) 30 min: Lenox Outlets Tanglewood festival Jacob Pillow 50 minutes to Mount Snow VT Manchester

Condo Near MASS MoCA

Welcome to Your Modern Bohemian inspired retreat centrally-located in North Adams! Experience a blend of contemporary comfort and bohemian charm in this freshly renovated home, just a 3-minute walk from Mass MOCA and downtown North Adams. A short 10-minute drive from Williamstown and 2 minutes from the VT border, Jiminy Peak a 30-minute drive away, kids' park is just a 2-minute walk, and close to the College of Modern Art and Williams College. This is the perfect base for exploring the region.

LuNo - Relaxing Ski and Culture Berkshires Escape

Insta: @LuNo_Airbnb Welcome to our dream ski getaway! This renovated home “LuNo” is ideal for up to 8 guests, featuring 3 bedrooms, 2 baths, and all comforts for a perfect Berkshires getaway. Cozy living area with smart TV, a fully equipped kitchen, and a private patio with a grill. Just 2 miles from Jiminy Peak and close to Tanglewood, Mass MoCA, and The Clark Museum, this condo offers both adventure and relaxation. Unwind at the community pool in summer and enjoy scenic beauty year-round.

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

Serene+Stylish Mountain Retreat

Our beautifully-designed, comfortable, much-loved townhome is great for families or friends wanting an escape to the Berkshire mountains. Located up the hill from Jiminy Peak Village Center, the home has 4 bedrooms over 3 floors, an open plan living space, updated kitchen, family room, and new deck. A short walk to the slopes in winter and use of Jiminy Peak resort pools in the summer make it a year-round destination. Book your stay and find out why once you are here, it’s so hard to leave!

Family-Friendly Hancock Home: Walk to Slopes!

Situated in the town of Hancock, 'Whistling Birches' offers guests 4 bedrooms, 3 bathrooms, a prime location just steps from the Jiminy Peak Mountain Resort, and ample in-home amenities that provide a comfortable and convenient vacation experience. Spend your days practicing slaloms down the slopes, then return home and ease your muscles with a dip in the hot tub! Prepare dinner in the fully equipped kitchen or fire up the BBQ before relaxing under the stars by the warmth of the fire pit.

Sophie’s House/Walk to Mass MoCa/Downtown

Newly updated with historic touches, this home from 1870 is a 15 min walk to Mass MoCA and downtown North Adams. Enjoy a quiet retreat with off-street parking, perfect for a friends and family getaway. Take in the beautiful historic neighborhood and indulge in all of the outdoor and cultural activities the Berkshires have to offer! The Willams College Museum of Art, as well as hiking and skiing, are just a short drive away. You don’t have to do any chores! Just enjoy your vacation!!

Five-Star Family Friendly Townhouse

Bring the whole family to this beautiful, spacious condo in the heart of Jiminy Peak. Enjoy the Jiminy Peak Mountain Resort and explore the Berkshires during Spring, Summer, and Fall in this highly desirable Mountainside setting. This destination resort offers great off-season recreation. Attractions include a Mountain Coaster, Alpine Slide, Trampoline Park, Aerial Adventure Park. Guests can also enjoy 2 Outdoor Pools, Tennis Courts, Christiansen's Tavern, The Country Store, and more.

Luxurious Historic Farmhouse

Relax with the whole family at this peaceful Historic Farmhouse Retreat with Modern Luxuries in the Berkshires. Welcome to Constitution Hill Farm, a meticulously restored 1750s New England farmhouse nestled on 196 acres of hardwood forests and lush meadows. This home seamlessly blends historic charm with contemporary comforts, offering an idyllic retreat for up to 14 guests. Enjoy the warmth of wide plank floors and beams, complemented by modern furnishings for a cozy ambiance.

Heart of Lenox Townhouse 2 Bedroom, 2 Bath

Just steps from town center, enjoy a special location in our quiet family neighborhood. Lenox offers gourmet restaurants, historical buildings and boutique shopping. Our new mini-split system offers individualized cooling/heating inside and a covered porch in front and a patio in back provide relaxing spaces outside. We still have the last 3 weeks of August available. There is a 1 week minimum but time can be extended upon request. Look forward to a Beautiful Berkshire Summer!

Beautiful Jiminy Peak Townhome Family Friendly

Leave the city behind and come work remotely from our 3 bedroom, 2 bathroom newly renovated townhome. Whether you're visiting the Berkshires area in the winter for skiing at Jiminy Peak, or you're seeking summertime adventures on the lakes and the hiking trails, this 3 level home with puts you right in the middle of the action. Perfect for families, this rental is located in a community just a mile (3 minute drive) from the mountain and managed by Moresi Property Management.

Upscale Architecturally Designed Berkshire Home

This spacious stylish home is one side of a duplex, 3500 square feet--perfect for group and family trips. Your privacy while visiting is important to us and will be respected. Most of the time, during your stay we will be at our apartment in NYC. We are offering a $500 nightly stay for the months of January and February of 2026 with a minimum stay of 7 nights. It is a discount of $100 off our regular pricing, and will include weekly cleaning for a stay of more than 12 days.