Villas and Holiday homes in Lenox, MA

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 modern A-frame cabin is located in Lenox, just a short walk from Tanglewood, Kennedy Park, and Kripalu, offering easy access to cultural events, outdoor recreation, and wellness activities. The property has consistently received excellent ratings for location, cleanliness, and overall guest experience.
The cabin features a split-level mezzanine design, offering a blend of modern and rustic charm, and can accommodate up to six guests. Enjoy stunning views of the Berkshires from the open living room with triple-height ceilings, relax on the sun porch or deck, or unwind in the garden hammocks. The cabin also includes a fully equipped kitchen, a private garden, a ping pong table, and BBQ facilities available upon request.

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.

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 private guest house is located in the centre of Lenox, just 1.6km from Tanglewood and Cranwell Spa & Golf Club. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience.
The house has 3 bedrooms and 3 bathrooms, covering 177 square metres and comfortably accommodating up to 6 guests. It features a fully equipped kitchen with a fridge, microwave oven, and dishwasher, free Wi-Fi, and parking.

This secluded guest house is situated less than 1 kilometre from Tanglewood and a short walk to Lenox, with Stockbridge Bowl nearby.
This newly remodelled barn sleeps six and features a full kitchen, air conditioning, Wi-Fi, a garden, parking, and a tiered patio with seasonal access to an herb and vegetable garden, offering proximity to ski resorts and cultural attractions.

This lakeside detached house in Lenox is located 2.7 kilometres from Cranwell Spa & Golf Club and 5.9 kilometres from Tanglewood Musical Center.
This detached house offers 200 square metres of floor area, features a kitchen, air conditioning, a terrace, a garden, free WiFi, private parking, and includes kayaks for guests exploring the lake.

This renovated dairy barn is situated in the Berkshires, just 2.4 kilometres from Stockbridge's Main Street and the Red Lion Inn, a short drive from Tanglewood and the Stockbridge Bowl, and under 16 kilometres from Lenox. The property has received excellent ratings for its location, cleanliness, and overall experience.
The two-bedroom property comfortably accommodates four guests. Enjoy a window seat with local coffee, BBQ grilling, a large Roku TV for movie nights, and the option to order delicious home-cooked Indian meals prepared by the owner.

This four-bedroom, three-and-a-half-bathroom house in Pittsfield, Massachusetts offers stunning views of Mount Greylock and convenient access to Berkshires cultural attractions.
The property, suitable for eight guests, boasts a swimming pool, ample parking, central air conditioning, and direct access to hiking trails; internet access is also provided.

This four-bedroom, three-and-a-half-bathroom house in Pittsfield, Massachusetts offers stunning views of Mount Greylock and convenient access to Berkshires cultural attractions.
The property, suitable for eight guests, boasts a swimming pool, ample parking, central air conditioning, and direct access to hiking trails; internet access is also provided.