House vacation rentals in Great Barrington

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.

Best of the Berkshires + Hot Tub by Evergreen Home

Evergreen Home Vacation Rentals invites you to this stylish 2-bed, 1-bath cottage, just 10 minutes from Catamount and 7 minutes from Great Barrington. This renovated 50s gem features a chef’s kitchen and a 500 sq. ft. deck with a private hot tub. Enjoy thoughtful touches like yoga mats, a record player, and a backyard hammock. Whether you're here to ski, hike, or shop, it is the perfect Berkshires base. Monthly ski rental discounts are available! Inquire today to secure your winter escape.

Cozy lakehouse

Relax with family or friends at this sweet cottage on Center Lake in the Berkshires. This lakeside cottage is charming and rustic. Enjoy a beautiful day on the lake swimming, fishing off the dock and kayaking. Grill dinner on your private deck and watch the stars come out in the evening Or enjoy all that the Berkshires have to offer, Jacob’s Pillow (15 min), Berkshire Theater (20 min), Tanglewood (30 min). There are plenty of nearby hiking trails and charming towns to explore.

Belle Meade

Open concept home with a Zen feel and made for relaxation. Nestle into the covered porch and spend hours of peaceful contemplation with nature all around! When you’ve had enough recharging, plan a backroad trip to endless possibilities. Tanglewood and Jacob’s Pillow are nearby via beautiful country roads. There are hikes for any level. Great restaurants, farmer’s markets and Guidos gourmet market just minutes away. Eat out or stay in with a cook’s kitchen and grill deck.

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.

GB at your doorstep

Our home is in the heart of vibrant downtown Great Barrington, just steps from the River Walk. Stroll a block to the vibrant shops, eateries, farmer's market, and historic Mahaiwe Theater. It's a quick 20 minute drive to the world class music at Tanglewood and the theater productions at Shakespeare & Co. Winter sports enthusiasts will be 5 minutes to Ski Butternut and 15 minutes to Catamount Ski Mountain. Relaxation at Lake Mansfield is only minutes away by car.

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

Berkshire Getaway~ No Pet Fee! Walk to Distillery

Hi! Welcome to the Berkshires! Enjoy total privacy on a full acre overlooking 200 acres of protected conservation land. Cozy nights by the fire, beautiful views & everything you need in our fully stocked home, just 8 min from Great Barrington. Steps from Berkshire Mountain Distillery, with a Peloton, pet-friendly yard & easy access to hiking, skiing, antiquing, restaurants & more! Please note: our seasonal hot tub is unavailable until further notice.

Walk to Town! Great Barrington 4-bedroom farmhouse

Enjoy the yard and garden at this charming 4-bedroom in-town farmhouse. The garden features various fruits and vegetables in season. Stroll to Great Barrington's restaurants and shops. Hike the woodland trail up the hill for a swim at nearby Lake Mansfield. Retreat to the private garden hideaway. This place has something for everyone who wants to relax in a cozy setting yet still be near everything Great Barrington has to offer.

Prime location for the best of the Berkshires

Our warm and welcoming little house has been designed and outfitted to be highly accommodating and comfortable. Our country living location is private but also super convenient: just a mile from Butternut Basin Ski Resort; walking distance to the Appalachian Trail; an easy 5 minute drive to Main Street Great Barrington; and shopping for staples is likewise close by.

Never too early to book for the Holidays & NYE!

My place is close to restaurants and dining, family-friendly activities, nightlife Tangelwood, Jacobs Pillow, Mahaiwe Arts Center, Arlo Guthrie Center. You’ll love my place because of the privacy, the views, the location, the ambiance, the outdoors space. My place is good for couples and families (with kids). It has new geo-thermal central heat and AC.