Places to stay in Stockbridge, MA

This spacious six-bedroom house, known as the General Williams house, is situated in Berkshire County, Massachusetts, 3.2km from Stockbridge centre and 8km from Lenox centre, offering easy access to the Mass Pike.
The 511-square-metre property boasts two fully equipped kitchens, six fireplaces, a games room, a swimming pool, and a spa, accommodating up to 16 guests and providing ample space for families or large groups.

The Ponds at Foxhollow by Capital Vacations is located in Lenox, Massachusetts, just a short drive from Tanglewood and the Tanglewood Musical Center, making it a great choice for music lovers and those looking to explore the scenic Berkshires. The resort enjoys excellent location and cleanliness ratings, with guests consistently praising its comfortable and well-maintained accommodation.
Each apartment features a fully equipped kitchen and a dining and seating area with a TV, providing everything you need for a relaxing stay. Guests can enjoy a range of amenities, including a seasonal outdoor pool and hot tub, an indoor pool, sauna, fitness center, and tennis court, as well as free bicycle use, fishing, and canoeing opportunities.

This pet-friendly holiday let in Housatonic is situated within walking distance of Art and Industry and a 5-minute walk from Housatonic River, offering convenient access to local attractions and outdoor pursuits.
This 3-bedroom flat accommodates up to six guests and features a fully equipped kitchen, air conditioning, on-site parking, and a private terrace or balcony, perfect for exploring Great Barrington and nearby ski resorts.

This riverfront duplex in Great Barrington offers a tranquil setting with scenic water views, situated minutes from the town centre and approximately 1.6 kilometres from the Mahaiwe Performing Arts Centre and 4.8 kilometres from Chesterwood.
This three-bedroom flat, accommodating up to eight guests, features a fully equipped kitchen with a microwave oven, spa facilities, and parking, with opportunities for outdoor pursuits such as skiing and ice skating nearby.

This Lenox apartment, a peaceful one-bedroom condo near the Pleasant Valley Wildlife Sanctuary, offers easy access (distances unspecified but likely within a few kilometres) to cultural attractions such as The Mount and the Frelinghuysen Morris House and Studio.
Sleeping four guests, the property boasts two bathrooms and is likely fully equipped, providing a tranquil base for exploring Lenox's natural and cultural offerings, including the Berkshire Scenic Railway Museum and The Bookstore.

This modern log cabin-style flat offers refined rustic charm with mountain views, located a mere 1600 metres from West Stockbridge's centre and under 15 minutes by car from Tanglewood.
This spacious 4-bedroom, 3-bathroom residence accommodates up to 9 guests and features a private heated saltwater pool and hot tub (open seasonally), a well-equipped home gym, a dramatic great room with a stone fireplace, and beautifully landscaped grounds with a fire pit.

This charming apartment is situated in Lenox, a short distance from popular ski areas like Bousquet and Butternut, making it ideal for a winter getaway. The apartment is located in a beautifully renovated 1840 Victorian home, offering a unique and charming experience. This cosy flat has a private entrance and a fenced-in patio, perfect for relaxing outdoors. The apartment is equipped with a full kitchen, a shared swimming pool, a large backyard with a fire pit, a shared garden, and laundry facilities.

This two-bedroom, two-bathroom apartment in Lee, Massachusetts offers convenient access to Berkshire attractions such as Tanglewood, Jacob's Pillow, and the Norman Rockwell Museum, and the Premium Outlets, with various ski areas also within driving distance (distances unspecified).
The self-catering flat sleeps six, boasts a fully equipped kitchen including a dishwasher, and features a swimming pool, jacuzzi, garden, fitness centre, and parking, plus a pet-friendly policy (with a £112 fee and pet vaccination proof required).

This Stockbridge cottage, a 19-minute walk from the Norman Rockwell Museum and 9.7km from Tanglewood, offers a peaceful setting near popular attractions.
The 257 square metre property sleeps eight guests in four bedrooms and three bathrooms, boasting a fully equipped kitchen, Wi-Fi, a garden, parking and air conditioning.

This Great Barrington house, located in a secluded wooded area offering easy access to the town centre, provides a tranquil retreat near local attractions.
Sleeping up to 15 guests, this self-catering property boasts a fully equipped kitchen, four bathrooms, a hot tub, private garden, and free Wi-Fi; nearby hiking trails and Great Barrington's cultural offerings provide ample entertainment options.

This five-bedroom cottage in Lee, Massachusetts, is a short drive from attractions such as the Berkshire Botanical Garden and the Norman Rockwell Museum.
The 189-square-metre (2,033 sq ft) property sleeps twelve, boasts a country-style kitchen, a clawfoot bath, and offers AvantStay amenities including 24/7 support and optional extras.

This three-bedroom apartment is situated on a private road, just under 2km from Stockbridge town centre, an 8-minute drive from Ski Butternut and a short drive from Great Barrington. The property has excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The apartment is spacious and modern, comfortably accommodating up to seven guests. It boasts a fully equipped kitchen, a private patio with a hot tub and fire pit, and a range of amenities including high-speed internet, a fireplace, and a laundry room. Guests can enjoy access to nearby hiking trails, lakes, mountains, art galleries, and the charming countryside.

This apartment is located in the Berkshires, just 5 kilometres from Stockbridge, Lenox, and Great Barrington, offering a peaceful retreat in a secluded forest setting. The apartment has received excellent ratings for its location, cleanliness, and user experience.
The apartment has 3 bedrooms and 2 bathrooms, providing space for up to 8 guests across 177 square metres. Guests can enjoy a range of amenities including a fully-equipped kitchen, multiple entertainment areas, a dedicated workspace, a family-friendly play area, a garden, a spa, a tennis court, and parking.

This apartment is located in The Ponds at Foxhollow Resort in Lee, Massachusetts, just a short distance from the picturesque Berkshire Mountains. The resort is situated near a tranquil pond, offering scenic views and a peaceful atmosphere.
This comfortable apartment, suitable for up to four guests, features a master bedroom with a king-size bed, a master bathroom with a jacuzzi, a fully equipped kitchen, a dining area, and a living area with a double sleeper sofa. The apartment benefits from a range of amenities including a swimming pool, jacuzzi, sauna, fitness centre, and free Wi-Fi, alongside a variety of activities such as tennis courts, a putting green, and access to bicycles for exploring the surrounding area.

This South Lee holiday home is situated less than 2km from the Housatonic River, Berkshire Botanical Garden, and Chesterwood, and within 5km of the Norman Rockwell Museum and Mission House.
The self-catering property boasts a fully equipped kitchen with microwave and dishwasher, 1.5 bathrooms, a fireplace, free Wi-Fi, parking, and air conditioning, perfect for exploring Stockbridge's attractions.

This apartment in Stockbridge is located just a short drive from the Berkshires, making it ideal for exploring nearby attractions such as Tanglewood and the Norman Rockwell Museum. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
This spacious four-bedroom property spans 186 square metres and can accommodate up to eight guests. The apartment offers a range of features, including a private swimming pool, a garden, a terrace, and a fully equipped kitchen, making it perfect for a relaxing and enjoyable stay.