Vacation Rentals in Stockbridge, MA

This apartment is located just a short distance from Great Barrington, offering a peaceful retreat surrounded by fields, woods and a lake. The area is ideal for those seeking a tranquil escape from the hustle and bustle.
The spacious apartment can comfortably accommodate up to nine guests and features five bedrooms and two bathrooms. Enjoy a range of amenities including a kitchen, swimming pool, parking and internet access, as well as the chance to explore the surrounding natural beauty.

This three-bedroom holiday home is located on 17 acres in the Berkshires, a 10-minute drive from Lenox and Great Barrington.
This family-friendly property accommodates up to eight guests and features air conditioning, a dishwasher, Wi-Fi, and a garden with a deck and fire pit, offering a secluded escape with excellent ratings for location, cleanliness, and user experience.

This Richmond property is situated just 3.2 kilometres from Tanglewood, a world-renowned music venue, and close to other attractions in the Berkshires. The accommodation has excellent ratings for cleanliness, location, and user experience.
This four-bedroom, four-bathroom house can comfortably accommodate up to ten guests. It features a large screened porch with a dining table, seating areas, and a water fountain, perfect for enjoying the outdoors and relaxing in a tranquil setting.

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 spacious farmhouse is located in Lee, just a short distance from the town centre, restaurants, and grocery stores, offering a peaceful escape in the countryside. The property has received excellent ratings for cleanliness, location, and overall user experience.
The farmhouse is a large, one-level property with ample space for up to 9 guests. It offers a fully equipped kitchen, a private garden, parking, and air conditioning, as well as a range of outdoor activities including fishing, birdwatching, and walking trails.

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 spacious house is situated on a mountain slope in the Berkshires, just 15 kilometres from the Butternut and Catamount ski resorts, offering a peaceful escape amidst scenic surroundings. The accommodation has received excellent ratings for its cleanliness, location, and overall user experience.
The property comprises a main house, a guest house, and a large barn, comfortably accommodating up to 16 guests. The property offers a range of amenities, including a chef-inspired kitchen, a swimming pool, a hot tub, a fire pit, bikes, and a basketball hoop, ensuring a memorable stay for all.

This mid-century modern deck house is located on a premier road in Lenox, less than 1.6 kilometres from Tanglewood, downtown Lenox, and Stockbridge Bowl, offering easy access to the area's cultural attractions and natural beauty. The accommodation has received excellent ratings for its location, cleanliness, and overall user experience.
The house has three bedrooms and one bathroom, accommodating up to six guests. It features a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, a garden, parking, internet access, and a private deck overlooking the surrounding woods.

This Stockbridge loft apartment is centrally located, within walking distance of Norman Rockwell's home and Stockbridge village centre.
The one-bedroom flat offers a galley kitchen with fridge, freezer and microwave, a private bathroom, and accommodates two guests, featuring original fireplace and idyllic views.

This holiday home is located in the mountains of West Stockbridge, within a 5km radius of attractions such as Hoffman's Pottery and Chesterwood. It has received very good user ratings.
The house offers 3 bedrooms and 4 bathrooms, accommodating up to 6 guests, with a total floor area of 297 square metres. Guests can enjoy a fully equipped kitchen, a fireplace, a terrace, a garden, and free Wi-Fi.

This charming apartment is located in Lenox, just a short walk from the town centre and close to attractions like Tanglewood and Shakespeare & Company. The surrounding area is peaceful, with a mix of historic buildings and modern amenities.
This spacious property has 10 bedrooms and 9 bathrooms, comfortably accommodating up to 15 guests. Enjoy a range of amenities including a swimming pool, jacuzzi, garden, and parking for up to 8 vehicles, as well as a fully equipped kitchen, modern conveniences, and outdoor recreation areas.