Alquileres vacacionales con patio en Stockbridge

Best of the Berkshires + Hot Tub by Evergreen Home

10 MINUTES TO CATAMOUNT Ski, hike, shop, and dine with this beautiful 2-bed, 1-bath Berkshires cottage as your home base. 7 minutes to downtown Great Barrington, this stylish, cozy rental has everything you need for a great getaway. A new renovation brings modern amenities to this classic 50’s cottage. Enjoy a chef’s kitchen, 500 sq-foot deck with hot tub, and thoughtful touches like yoga mats, a record player, board games, and a backyard hammock. Monthly ski rental discounts are available!

Cozy Hilltown Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

Stylish Shales Brook Cottage-Cozy up to happiness

Bright & inviting! Welcome to our charming cottage, a stylish 2-bedroom, 2-bath retreat by Shales Brook. Relax on cool evenings beside the vintage Malm wood-burning stove. Enjoy modern comforts with central air, a screened-in porch, and a deck overlooking the tranquil waters of Shales Brook. The soothing sounds of the brook enhance your stay.. Located near fabulous Berkshire attractions, fantastic hikes, 15 minutes to the town of Lee, minutes to Jacob‘s pillow and 20 minutes to Tanglewood,!

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

Home in Great Barrington. Steps from downtown!

First Things First… Let’s Keep the Love Alive! ❤️ 🙌 Central and Private! Just steps away from historic downtown Great Barrington. East Mountain Hiking trails are a quick walk away. Enjoy sunset views with friends and family, before you walk into town for a night out! Butternut Ski Area: 5-10 min drive(traffic depending) Tanglewood: 20-25 min This new home features all new appliances and furniture. Enjoy luxury, charm, and privacy while you rest easy at The Maple. 🫶

King Bed |Wi-Fi| 2m to Ski Resort

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. * 1.5 miles to Downtown * 1.3 miles to Mahaiwe Performing Arts Center * 44 miles to Albany International Airport *4.5 miles to Great Barrington Airport KEY FEATURES: *MCM Design * Plush King Sized Bed w/ high end Centium Satin Linens *High Speed Internet *58" Smart TV

3-bedroom Berkshire bungalow on 2.5 peaceful acres

Modern farmhouse bungalow with private bridge and brook! Offering privacy as well as nearby nightlife, set upon 2.5 acres of beautiful Berkshire landscape but only 7 minutes to downtown Great Barrington and a short drive to Catamount and Butternut ski area. Mountains, waterfalls, countless hikes and bike routes, farmers' markets, coffee shops, breweries, Shakespeare and Co, Tanglewood, and world-class restaurants all come together in this quintessential New England community.

Catskill Cottage | Walk to Downtown & River Views

Nestled just steps away from the heart of Main Street, the Catskill Cottage beckons you to experience the charm of Upstate living like a true local. This inviting retreat boasts rustic exposed brick walls, a sleek industrial-style kitchen, and a modern bathroom. As you step outside, you'll find convenience and adventure at your fingertips. Vibrant local shops, delectable cuisine at nearby restaurants, an the tranquil of the river are all just a short walk away.

Catskill Village House - Mountain View Studio

Our largest option, the Mountain View Suite incorporates high ceilings, and mountaintop views from a raised dining area to provide a large and light oasis. Located on the second floor, the suite features custom antique accents and original artwork that evoke a sense of adventure. The room includes a large bath with clawfoot tub and shower, kitchenette, and sleeper sofa. Custom queen mattress (featured at the Four Seasons NYC), organic cotton sheets.

Boutique TINY home+private HOT TUB-walk to Main St

Blush & Bubbles for December stays. Romantic, boutique-luxe tiny home with private hot tub, firepit, and dreamy loft lounge. Plush queen bed, full kitchen, and curated charm throughout. A peaceful oasis just 2 mins from Chatham’s Main Street lined with restaurants, brewery, shops & theater. The perfect upstate NY getaway for couples—hike, visit galleries, stroll to dinner, or unwind in your own private spa oasis at @artparkhomes.