Townhome holiday rentals in Berkshire County

24 Main: Historic Twin Home 2

Welcome to the Berkshires! A large two family home thoughtfully designed and nestled in town center. Rent one side or both sides of the house opening it up to accommodate a larger family or group of friends for a memorable vacation right in the heart of Egremont on Main Street. The location couldn’t be better, pop out of the house and stroll down newly paved sidewalks around town, where we have a few restaurants and shops. Whether you rent one side the other side or both, you will have privacy.

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.

Walk to campus, Mohican trail, river restaurants

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 <12 min drive: VT North Adams Mass MOCA hiking 20 min: Jiminy Peak (skiing and summer park) Ramblewood Adventure park Zipline Lakes (rent boats, fish) 30 min: Lenox Outlets Tanglewood festival Jacob’s Pillow Manchester

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!

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.

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.

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure ★☆ ABOUT THIS SPACE ☆★ Welcome to Jiminy Peak Slopeside Getaway, your all-season mountain retreat. Enjoy scenic views and a true ski-in/ski-out experience—just a 3-minute walk to the chair lift at Jiminy Peak. This 2-bedroom, 2-bath home sleeps up to 7 guests and offers private parking, a porch, and a deck, plus access to a heated pool, indoor/outdoor hot tub, and clubhouse.

Victorian 2br on the Hill

Your friends or family will be close to everything when you stay at this centrally-located Victorian Gem. This historic townhouse is just a 3 min drive or 13 minute walk to MassMOCA and less to other shops and local restaurants. 2 total bedrooms with 2 Queen beds. Unique dining, living, and kitchen areas to cook, play games, or just hang out and relax House has ample off street parking.