Townhome vacation rentals in Berkshire County

4.94 out of 5 average rating, 33 reviews

A bright entrance area features a staircase leading to upper levels. To the left, a spacious living area is seen with a light-colored sofa, a patterned area rug, and a large window allowing natural light. Decorative elements such as plants and artwork add warmth to the space.

Townhouse in North Adams

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.

4.92 out of 5 average rating, 25 reviews

Townhouse in Lee

Art-Filled Berkshire Retreat on 2 Acres

Settle in the Berkshires in a spacious, art-filled 3,500-sq-ft home designed for gathering and relaxing. Set on 2 private acres in Lee, it features 4 bedrooms, 3 baths, a wood-burning fireplace, and a chef's kitchen. Perfectly located near Lenox and Stockbridge, you are minutes away from museums, theaters, hiking, and skiing. Ideal for up to 6 guests, families, or remote work. Pets welcome! Now booking extended winter stays for Jan & Feb 2027 (3-night min). Weekly cleaning included for 12+ days

The exterior of the condo is shown covered in a blanket of fresh snow, emphasizing its charming, sloped roof. A snow-laden evergreen tree stands nearby, while a gently sloped pathway leads to the entrance, inviting guests to explore the winter landscape.

5.0 out of 5 average rating, 14 reviews

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.

A peaceful scene reveals a winding road leading through a residential area with well-maintained homes. Snow-covered mountain slopes are visible in the background, flanked by trees that display early signs of changing seasons.

4.92 out of 5 average rating, 115 reviews

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.

The exterior of a townhome is shown covered in fresh snow, with a covered porch and white railing. Flanked by evergreen trees, the structure features a gabled roof and a single round window above the front entrance, adding character to the picturesque winter scene.

5.0 out of 5 average rating, 43 reviews

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!

Private room in Pittsfield

Modern, Spacious Master Bedroom and Bathroom

Hi, I'm Isla, This Master bedroom is large and bright with a King sized bed, TV, an Office’s desk and large bathroom with access to a backyard facing the deck. You will have exclusive use of a spacious kitchen and dining room area. The Townhouse is located in a cull de sac in a private community, so it is very quiet and safe. Includes a spacious, clean and bright kitchen fully stocked with pots, pans and utensils. Conveniently located close to everything the Berkshires has to offer.

4.93 out of 5 average rating, 107 reviews

A spacious living area features a sectional gray couch adorned with colorful throw pillows. A wooden coffee table sits center stage, complemented by an area rug. A modern lamp provides soft lighting, while a fireplace maintains a cozy ambiance. Abstract art hangs on the wall.

5.0 out of 5 average rating, 7 reviews

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.

Townhouse in Williamstown

A spacious living area is furnished with a yellow sofa and a gray sectional. Light wood flooring is complemented by a patterned area rug. Natural light enters through large windows, while a ceiling fan provides airflow. Decorative plants and framed artwork enhance the inviting environment.

Walk to Williams college and town | sleeps 6

Quiet, comfortable townhome sleeps 6 w/ tranquil river/walk/bike path down the street. Traveling with a larger group? Our nearly identical townhouse next door is also for rent for 5 guests. Message me for availability. 15 Walk to: Williams College/restaurants 5-15 min: The Clark Sand Springs (public pool) North Adams, Mass MOCA 30 min: Jiminy Peak (skiing/ summer park) Ramblewood Adventure park Lenox Outlet Tanglewood Jacob Pillow Vt farms 50 min to Mt Snow, Manchester

4.94 out of 5 average rating, 79 reviews

Superhost

Townhouse in Lanesborough

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.

4.9 out of 5 average rating, 10 reviews

A snow-covered entrance showcases a wooden sign featuring 'SMITH UNITS 1061 - 1064.' The residential building, adorned with white siding, includes a window unit air conditioner protruding from the wall. Surrounding shrubs are blanketed with fresh snow.

4.83 out of 5 average rating, 109 reviews

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.

Townhouse in Cheshire

4 Bedrooms first floor home.

Relax with the whole family in the heart of Cheshire a peaceful place to stay. first floor apartment equipped kitchen and bathrooms for you .4 minutes away from bike trail that goes through beautiful views scenic lakes and beauty all year long and just minutes away from all sites that beautiful Berkshires has to offer 10 minutes from Jiminy peak and 15 minutes to any hospital from the region like BMC and North Adams Hospital.

4.7 out of 5 average rating, 10 reviews