Guesthouse holiday rentals in Western Massachusetts

Mill River Cottage (pet friendly!)

Welcome to our peaceful and unique urban farm cottage. We are located in historic Florence, Massachusetts (a part of Northampton). While our place is no longer a working farm, the cottage was created many years ago to support the main dwelling. It has been modernized to offer every comfort while maintaining its cozy aesthetic. Free parking & lighted access to the cottage. The cottage is a private space where you can come and go as you please. Relax and unwind or head out to explore the area!

Family · Location · Getting around

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

Value · Location · Sleep quality

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!

Location · Value · Sleep quality

Cottage beside a waterfall

Our 1840’s renovated grist mill is located in the beautiful Monadnock Region. The house and cottage are situated on twelve acres and includes gardens, an orchard, berry bushes, grape vines, beehives, a dog, and a tremendous waterfall. We are close to many of nature’s gems including Mount Monadnock, Pack Monadnock, the Heald Tract hiking trails, skiing, snowshoeing and swimming. Also the acclaimed MacDowell Arts Center, Andy’s Summer Playhouse, Andres Institute of Art and the Waldorf Schools.

Location · Value · Solo travel

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.

Value · Family · Cleanliness

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.

Location · Value · Decor

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

Value · Location · Solo travel

Stylish Woodstock Guest House..Mountain View

This 1920's converted barn has the original beams and antique fixtures w/vintage and new furnishings. The french doors on one complete wall amplify the open space with views of the Catskill Mts., pond, fields, and the vast sky. No smoking no pets. You love them, I love them, but they cannot stay here. Also, two night minimum stay. Three night minimum on holiday weekends.

Family · Value · Nearby

Little Blue Studio

Gorgeous, unique guest house with cathedral ceilings, cupola, front and back decks, three-wall screened porch, fully functional kitchen with Wolf stove, dishwasher, full-sized refrigerator, a/c, ceiling fans, appleTV, internet, two woodstoves (gas, wood). One mile from downtown Northampton, near Childs park, retreat-like environment. Unforgettable space!

Value · Location · Biking

The East Street Cabin

This adorable cabin is your perfect escape for rest and relaxation. This is a perfect place for people coming to the Berkshires for Tanglewood or any of the other wonderful things the area has to offer. The cabin is located down a path through the woods about 100 yards from the main house. We are excited to share our cabin with you.

Family · Location · Comfort

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.

Location · Family · Skiing

Modern cottage with Hudson River view

Relax and enjoy your stay in a bright, modern cottage with windows overlooking the river and a wraparound deck. Whether you are looking to relax along the river, explore Hyde Park historic properties or discover the incredible natural beauty of the Hudson Valley, this cottage is an ideal escape.

Location · Family · Biking