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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.

Modern barn in the heart of the Berkshires

Modern, renovated dairy barn in the heart of the Berkshires. Located on 3.5 acres with beautiful views and close to everything. 1.5 miles to Main St Stockbridge/Red Lion Inn, 5 minutes to Tanglewood, 5 minutes to the Stockbridge Bowl and beautiful hiking trails, under 10 minutes to Lenox . This is the perfect base for exploring the Berkshires or a great getaway for relaxing and enjoying nature. Family and pet friendly! *Please read Interaction with Guests section before booking*

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Step into a beautifully preserved piece of Berkshire history. Originally built in the 1880s, this renovated one-bedroom guesthouse perfectly blends historic charm with modern luxury. Whether you are hitting the slopes, leaf-peeping, or looking for a quiet romantic escape, this stylish retreat serves as your perfect base camp. Nestled in the beautiful, tranquil village of Southfield, MA, you are surrounded by the best of the Berkshires while staying steps away from local favorites.

Guest House in Stockbridge 3 miles to Tanglewood

A bike ride to downtown Stockbridge and 3 miles to Tanglewood and Kripalu.. Located in the Historic Interlaken section of Stockbridge. One bedroom guesthouse attached to 1829 colonial. One bedroom with queen bed and actual 100% cotton sheets from Pottery Barn. Living area with beautiful view of Larrywaug brook, full size pull out couch with 100% cotton sheets. Bath has shower-no tub. Equipped kitchenette. NO STOVE. 10 Miles to Great Barrington.

Bitty Berkshire Bungalow

Just 2 miles from historic Stockbridge's Red Lion Inn, 1 mile from the Norman Rockwell Museum and the Berkshire Botanical Garden, 15 minutes from Bosquet ski resort, 12 minutes from Tanglewood, and around the corner from Chesterwood, in the lush forest of Massachusetts' Berkshire mountains, this cozy "bitty bungalow" is the perfect place from which to foray out on wonderful adventures in this vacation wonderland, returning for quiet rest and renewal.

Private Guesthouse in Williamstown

Charming private guesthouse with shared pool use. Newly renovated, the space features high ceilings, queen sized bed, rustic Arts & Crafts furniture, heat/air conditioning, and kitchenette. Located in an outbuilding on the property, the guesthouse is close to woodland hikes, excellent biking, as well as many other attractions in the Berkshires. The beautiful in-ground pool is perfect for an afternoon dip - guest hours are usually between 3 - 5.

Modern studio with views of the treetops

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

Justice's Birthplace: King Bed, Hearths, Gardens

Relax in this charming 1815 Greek Revival on historic registry: original wide plank wood floors, exposed wood ceiling beams, hearths in each room. Only 6 miles to Tanglewood BSO concerts. Great location: Stockbridge (3 min Lee Outlets (4min Lenox (9min Kripalu (11min Austen Riggs (3min BMC (17min Convenient to culture: The Mount (8min Norman Rockwell Museum (9min Shakespeare & Co (9min Tanglewood (12min Jacob's Pillow (17min

Guest House at Stonover Estate

Located on historic Estate grounds, this is an aesthetically pleasing and private getaway for adults and couples. The town of Lenox hosts multiple 5-star restaurants, and the property is a 10 minute walk to town. It is 1 mile from Tanglewood, 1 mile to Shakespear & Co., and 14 miles to Jacob’s Pillow. If you like the outdoors, it is a half mile to Kennedy Park for hiking or biking.

Guest House near hiking trails and excellent cafés

Studio guesthouse is all yours. In a quiet valley near walking and hiking trails. Close to Tanglewood, the Stockbridge Bowl, and Kripalu. 10 minutes to downtown West Stockbridge and No. 6 Depot Roastery and Cafe. 15 minutes to Great Barrington. The guest house is on owner's property and there is a dog on the premises. Absolutely no pets or children under 18.

Hudson Valley and The Berkshires Cottage

Welcome to your luxury cottage escape. Located in the heart of the Hudson Valley in Hillsdale, NY sits a calm, stylish 1 bedroom cottage; perfect for a couple or a solo vacationer looking for solitude. We believe you’re here to completely relax, that’s why we have no requirements when checking out, just turn the lights off and lock the door!

Brookside Cottage

Drift off to the sound of a babbling brook outside the bay window in this cozy country cottage. Minutes from Downtown Williamstown, North Adams and Bennington, VT. We are about 20 minutes away from Jiminy Peak for downhill skiing. The trails behind our house are ideal for snowshoeing, nordic skiing, and snowman building.