House holiday rentals in Stockbridge

Nerd Preservation Sanctuary

Nerdscapist, geekmantic country home; perfect for oddballs who wish for a crafty, private, hilarious country retreat. Featuring a bad art print collection from the glorious MA Museum of Bad Art (Or Mass MOBA). Original bad art and sculpture. Much scope for the imagination's doofiest crevices. Redonkulously close to all the local fun: tiny drive to 5 lakes, Jacob's Pillow, Tanglewood 17 mi, Otis ski, 1/2 hr to Butternut Ski & Tubing Pittsfield & Great Barrington, hour to Berkshire E & Mass MOCA.

Net Zero home with rustic Berkshire charm

Be a part of the solution in our centrally located solar home that sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield! Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Enjoy custom concrete counters and wood floors in this open kitchen concept. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. We are emissions free! How cool is that?!

Elegant Year-Round Lakeside Retreat with AC

The Haven, an elegant cottage surrounded by woods, located on a pristine lake with private dock. 4 bedrooms, 3 baths. This year-round vacation cottage with hot tub provides an experience in the Berkshires you won’t forget! Leaf-peep in fall, ski in winter, hike in spring, kayak & swim in summer, or browse the boutique shops in quaint towns like Great Barrington, Lenox and Stockbridge. Newly installed mini-splits provide AC in all bedrooms and LVR/DR/Kitchen common area. 1 house-trained dog ok.

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

Berkshire 4 season home

The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

Heart of Lenox Walk to Town Cozy Cottage!

The cottage is a 2-minute walk to Church St., right in the heart of Lenox. Kennedy Park (1.5 miles) is a short stroll away for great hiking & biking, while multiple 5-star restaurants are all within a few minute walk. Tanglewood (2 miles), Kripalu (3 miles), Shakespeare & Co. (1 mile), Berkshire Theatre Festival & the Norman Rockwell Museum (7 miles), Butternut, Jiminy Peak (15 miles) & Bousquet (5 miles) ski area, Mahaiwe Performing Arts Center & Jacob's Pillow (14 miles) are all close by!

Cozy Berkshires Cottage

Stay in a cozy, newly remodeled Berkshires 1920's cottage! We've added bedrooms and a bathroom with a soaking tub upstairs, expanded the first floor bathroom and added a laundry room. The cottage is set back from the main road, easily accessible yet private. -Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. -Ideal for couples, adventurers, business travelers, and furry friends (pets). -Note: Stairs to the 2nd floor are steep: guests are responsible for child safety.

Peaceful Stockbridge Cabin in the Woods

The Residence is a beautiful, secluded home in the Berkshire foothills. The 14-acre property includes hiking trails through the woods, a meadow, and a lovely babbling brook. Despite its secluded feel, the house just a short drive from many of the area's favorite attractions. The Residence provides a wonderful for base for enjoying all that the Berkshires have to offer, though guests may decide to spend much of their stay exploring the rustic beauty of the property itself.

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relax by the firepit- we hope you enjoy your stay and will visit us again.

Relaxing Housatonic Retreat

This home is where my husband grew up and has been in his family for many years. It's currently my father-in-law's summer house and is in various stages of updating. The village of Housatonic is one of our favorite places on Earth! With quaint restaurants within a five minute walk, hiking trails nearby, spectacular foliage in the fall, and several ski areas to choose from, it has something for more active people or those who would just like a quiet, relaxing retreat.

Sun-filled, Charming Stockbridge Classic- In Town!

Beautiful remodel on a classic old, well-appointed New England house located in the middle of town on a dead-end road leading to hiking trails for Laura's Tower. A quick walk to Downtown Stockbridge, Red Lion Inn, gas station, cafes, markets, shops... everything you need. A park sits directly across the street with open acreage, swings, sandbox, skate park. Parking available on site. Located within minutes of four season activities- happy to make recommendations!

Stylish Mid-century Modern Berkshires Cape

Stylish and design forward, yet entirely comfortable for families and kids. Fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires. 15 minutes from Butternut ski to south + Bousquet to the north, 35 min to Jiminy Peak. Cozy up by the wood burning fireplace and enjoy the winter wonderland! The house is decorated in mid century modern style with gorgeous design touches throughout!