Places to stay in Stockbridge, MA

This Stockbridge holiday cottage, a four-minute walk from Stockbridge Bowl's town beach and a five-minute drive (approximately 3.2km) from Tanglewood, offers easy access to Lenox, Lee, and Stockbridge itself, all within a seven-minute drive (approximately 4.5km).
Sleeping up to five guests in two bedrooms and one bathroom, this well-maintained, family-owned property includes a kitchen, parking, internet access, and is perfect for exploring the Berkshires during spring, summer, and autumn.

This South Lee studio flat is situated in a Grade II listed 1815 barn directly on the Appalachian Trail, offering mountain and river views and proximity to Goose Pond Reservation and October Mountain State Forest (9.6 kilometres), as well as Stockbridge (3.2 kilometres) and downtown Lee (4.8 kilometres).
The 84 square metre studio loft accommodates up to four guests with a king bed and futon, a kitchenette, a laptop-friendly workspace, air conditioning, Wi-Fi, and a covered porch, with parking and pets allowed for an additional fee.

This Stockbridge apartment, near the Norman Rockwell Museum and Taglewood, offers easy access to Berkshire attractions.
Sleeping eight guests, the three-bedroom, one-bathroom property includes a kitchen with dishwasher, air conditioning, a garden, parking, and internet access.

This Stockbridge apartment, a self-contained flat, is situated 1.6km from Stockbridge town centre, offering easy access to Tanglewood, Stockbridge Bowl, and the Kripalu Center for Yoga & Health (all within a 16km radius).
The one-bedroom, one-bathroom dwelling sleeps four guests comfortably, boasting a private garden, parking for two cars, a riverside walking trail, a fire pit, and queen-size beds; nearby train noise should be noted.

Moss's Muse is a modern luxury residence in historic Stockbridge, Massachusetts, situated 800 meters from Tanglewood and a short drive to Stockbridge Bowl, Olivia's Overlook at Yokun Ridge Reserve, and the Norman Rockwell Museum. This 4-bedroom, 3-bathroom flat accommodates up to 8 guests and features a chef's kitchen, a dedicated workspace, a lower-level in-laws suite, and outdoor dining, with dogs welcome for a one-time fee.

This charming cottage is located in a peaceful lake neighbourhood in Stockbridge, just 1.6 kilometres from the public beach at Stockbridge Bowl. It has received excellent ratings for its location, cleanliness, and overall experience.
The 84 square metre cottage comfortably sleeps six guests and features a spacious outdoor area with a sunny deck, a charming fieldstone fireplace, and a dedicated reading nook. Enjoy the modern amenities including a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, a spa, and parking.

This charming apartment is located in Stockbridge, within easy reach of the town's main attractions, including the Stockbridge Bowl, the Norman Rockwell Museum, and the Berkshire Botanical Garden. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The apartment offers four bedrooms and two bathrooms, accommodating up to eight guests. It features a well-equipped kitchen, multiple living spaces, and expansive outdoor decks, making it perfect for families or groups of friends looking for a comfortable and enjoyable stay in the Berkshires.

This charming lodge is situated on the shores of Stockbridge Bowl cove, just 5 kilometres from the world-renowned Tanglewood music venue, offering a peaceful retreat amidst the beauty of the Berkshire region.
The property features three bedrooms and two bathrooms, comfortably accommodating up to seven guests. Enjoy a fully equipped kitchen, a large deck, an enclosed porch, and a spacious lawn, perfect for relaxing and enjoying the beautiful surroundings.

This charming cottage is situated in the quintessential Berkshire village of Stockbridge, just a short walk from the Red Lion Inn and within a 5-minute walk of hiking trails, a park, and tennis courts. The property has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and convenient stay.
This 158 square metre property has three bedrooms, two bathrooms, and can accommodate up to eight guests. The cottage features a well-equipped kitchen, a comfortable living area, a fenced-in backyard with mountain views, and a range of amenities including a foosball table, dart board, yoga mats, a Weber grill, a Solo firepit, and lake rights to the Stockbridge Bowl.

This secluded apartment, located on a quiet dead-end road in Stockbridge, offers a peaceful retreat with easy access to woodland and a stream, ideal for those seeking a tranquil getaway.
This pet-friendly flat accommodates up to six guests and features a well-equipped kitchen, air conditioning, two bathrooms, and an outdoor deck, with ample garden space for recreation and exploration.

This West Stockbridge holiday home, minutes from Tanglewood, Kripalu Centre for Yoga & Health, Lenox and Stockbridge town centres, and the Norman Rockwell Museum, offers convenient access to Berkshire attractions.
The 279-square-metre (approx. 3000 sq ft) property boasts five bedrooms, three bathrooms, sleeps eight guests, and includes a fully equipped kitchen, spa, garden, parking, and numerous amenities such as satellite TV and Netflix.

This West Stockbridge cottage, near Lenox, Massachusetts, enjoys a secluded location on 14 acres, a short drive (approx. 8 km) from Tanglewood and the Kripalu Center for Yoga & Health.
The single-bedroom, single-bathroom lodge sleeps four guests and features a fully equipped kitchen, air conditioning, a wood-burning stove, private garden, and parking; nearby attractions include wineries, museums, and ski resorts within a 24km radius.