Search accommodations in Stockbridge, MA

This ranch-style apartment is located on a quiet road in Lenox/Stockbridge, just a short walk from Tanglewood, the Lenox Town Center, Stockbridge Bowl, and local theaters. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travelers.
The home features three bedrooms and one bathroom, comfortably accommodating up to six guests. Enjoy convenient amenities like a fully equipped kitchen, air conditioning, a private garden, and parking, perfect for exploring the beautiful Berkshires.

This Stockbridge vacation home offers a central location, within a 10-minute walk of Schantz Galleries, the Housatonic River, and Mission House, and less than a mile from the Berkshire Theatre Festival and Naumkeag Museum.
This five-bedroom, two-bathroom house sleeps twelve guests and includes amenities such as free WiFi, a fully equipped kitchen with a refrigerator and dishwasher, a fireplace, and a washing machine; housekeeping is available upon request.

This five-bedroom, three-bathroom Victorian home in downtown Lenox, Massachusetts, is a three-block walk from the bus station and within walking distance of numerous restaurants and shops.
This spacious rental boasts a well-equipped eat-in kitchen, a private backyard with a terrace and gas grill, and parking for three cars (shared driveway, plus street parking April 1st-November 1st), comfortably accommodating larger groups near Kennedy Park, Ventfort Hall, The Mount, and Arrowhead.

This Stockbridge apartment is located just a short walk from the Norman Rockwell Museum and Chesterwood, offering easy access to two of the town's most popular attractions. The property enjoys excellent guest, location, and cleanliness ratings.
The apartment features 3 bedrooms and 2 bathrooms, comfortably accommodating up to 6 guests. Amenities include a fully equipped kitchen, air conditioning, parking, and internet access, along with a vintage modern design and hardwood floors throughout.

This Lenox, Massachusetts condo rental is conveniently located in the Berkshires, a short drive from The Mount (2.9 miles), Norman Rockwell Museum (7.2 miles), and Tanglewood (4.3 miles).
This two-bedroom, three-bathroom vacation home sleeps six guests and boasts a fully equipped kitchen, private deck with scenic pond views, access to resort amenities including indoor/outdoor pools, a fitness center, and a sauna.

This apartment is located in The Ponds at Foxhollow Resort in Lee, Massachusetts, close to Tanglewood, a world-renowned music venue, and the town's shops and restaurants. The resort sits in the picturesque Berkshire Mountains, near a scenic pond.
The apartment comfortably accommodates up to six guests in three bedrooms, including a master bedroom with a king-sized bed, a second bedroom with a queen-sized bed, and a living space with a double sleeper sofa. This apartment offers access to resort amenities such as indoor and outdoor pools, hot tubs, saunas, an exercise room, tennis courts, a putting green, and a variety of outdoor sports equipment.

This 6-bedroom apartment is located in Lenox, just a mile from the Lenox Center and 1.5 miles from Tanglewood, offering easy access to cultural events and attractions. Guests consistently rate this rental as excellent, praising its privacy, stunning views, and peaceful atmosphere.
This spacious home can comfortably accommodate up to 16 guests and features a wrap-around porch, a swimming pool, a sports court, and a garden. Guests can also enjoy fresh eggs from the on-site chickens and take advantage of the nearby hiking trails and natural beauty.

This charming cottage is located in a private lake community near Stockbridge, a short drive from Tanglewood, Lenox, and downtown Stockbridge, offering easy access to the area's attractions. The cottage has received excellent ratings for its location, cleanliness, and overall experience.
The three-bedroom, two-bathroom cottage comfortably accommodates up to six guests. Enjoy the peaceful forest setting, lakefront access, hiking trails, modern conveniences, and outdoor relaxation spaces, including a back deck, fire pit, screened-in porch, and a kayak for exploring the lake.

This Stockbridge apartment rental is conveniently located near the Norman Rockwell Museum and Taglewood, offering easy access to Stockbridge Bowl and the town's attractions.
The three-bedroom, one-bathroom unit sleeps eight guests and includes a fully equipped kitchen with dishwasher, air conditioning, a garden, parking, and internet access; enjoy nearby swimming, boating, and cultural experiences.

This historic Stockbridge apartment with 3 bedrooms and 2 bathrooms is in a convenient location, steps from the Red Lion Inn. It is near hiking trails, a park, and tennis courts (within 5 minutes walking distance). It has an excellent user rating, location rating, and cleanliness rating.
The apartment has a private, fenced-in backyard with mountain views and outdoor seating, lake rights to Stockbridge Bowl, a Weber grill and Solo firepit for backyard relaxation, comfortable beds with high-end bedding, high-speed internet, and unique furniture from Glenn Close's estate sale. It allows pets and is family-friendly. It has air conditioning, a kitchen with a fridge, freezer, microwave oven, and dishwasher, a fitness center, parking, and a garden. It can accommodate up to 8 guests.

This Lee, Massachusetts rental is conveniently located near the Premium Outlets, Tanglewood, and Jacob's Pillow, offering easy access to Berkshire attractions.
The two-bedroom, two-bathroom apartment sleeps six, features a fully equipped kitchen with dishwasher, and includes amenities such as a swimming pool, jacuzzi, fitness center, and parking; summer weekly rentals and negotiable February weekday rates are available.

This Lenox apartment is located in downtown Lenox, within walking distance of the Tanglewood Music Center and the Bookstore. The one-bedroom apartment sleeps four guests and features a fully equipped kitchen with a dishwasher, a queen-sized bed, and access to on-site parking.

This Richmond vacation rental is located just 3.2 miles from Tanglewood, a renowned music venue, and is close to other Berkshire attractions, making it a great base for exploring the region. It has earned excellent ratings for location, cleanliness, and overall user experience.
This spacious home has 4 bedrooms and 4 bathrooms, comfortably accommodating up to 10 guests. The property offers a screened-in porch with a dining table, seating areas, and a calming water fountain, perfect for enjoying the outdoors.

This Stockbridge cabin is located in a serene lake neighborhood with a charming bohemian interior, just steps away from the picturesque Stockbridge Bowl. It has excellent user, location, and cleanliness ratings.
The cabin has a floor area of 900 square feet and can accommodate up to 6 guests. It features a cozy sleeping loft, a reading nook, and a fieldstone fireplace. The spacious yard, sunny deck, and outdoor amenities make it perfect for relaxation and outdoor entertainment.

This charming 2-bedroom home is located in Stockbridge, a short walk from the village center and its attractions, including the Red Lion Inn and the Berkshire Theater Festival. The property offers a serene setting with backyard views of the Berkshire Hills and mature plantings, while still being within walking distance of the village center.
The apartment features a cozy living room with a baby grand Yamaha piano, a small upstairs sitting room with a sweeping view of the hills, and two bedrooms, one with a full canopy bed and the other with two twin beds. The apartment is equipped with a modern kitchen, a garden, parking, and two full bathrooms, making it ideal for families or groups of up to 4 guests.