Holiday Rentals in Lenox, MA

This spacious four-bedroom holiday home is located in Stockbridge, just a 4-minute drive from The Mount and a 7-minute drive from Shakespeare and Company, offering convenient access to local attractions.
This 253 square meter property features a fully equipped kitchen, air conditioning, Wi-Fi, and on-site parking, with outdoor space including a terrace and barbecue, comfortably accommodating up to 10 guests for a family-friendly stay.

This four-bedroom property is situated in Richmond, Massachusetts, a quiet neighbourhood just 1.5 kilometres from Balderdash Cellars and a 24-kilometre drive from Tanglewood. The apartment is highly rated by guests, receiving excellent reviews for its comfort and amenities.
The spacious home can accommodate up to 10 guests and features a large backyard with a fire pit and a screened-in porch with a dining area. Amenities include a fully equipped kitchen, central air conditioning, a garage for storing outdoor gear, a swing set, and an EV charger.

Lee Manor, situated in Lee, Massachusetts, is a 5-minute drive from Lee Premium Outlets and High Lawn Farm, and within walking distance of Lee's town centre, offering easy access to Tanglewood, the Norman Rockwell Museum, and other Berkshire attractions.
This five-bedroom, four-bathroom house sleeps fifteen guests, boasts a fully equipped kitchen, free Wi-Fi, and stylishly renovated interiors, perfect for families or groups exploring the Berkshires.

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.

Vacation house to rent. This accommodation is based in Lee.
Facilities and services: a terrace, a kitchen and a barbecue. Enjoy free parking with this accommodation in Lee!

This apartment is situated in Lenox, just 1.6 kilometres from the town centre and 2.4 kilometres from Tanglewood, offering a peaceful retreat close to attractions. It has been highly rated by previous guests, receiving excellent reviews.
This spacious apartment sleeps up to 16 guests and features six bedrooms and four bathrooms. Guests can enjoy a range of amenities including a swimming pool, a sports court, and a wrap-around porch, as well as fresh eggs from the chickens and beautiful gardens.

This one-bedroom flat in Pittsfield is conveniently located for exploring local culture and history, with Tanglewood Music Center and Colonial Theater just a short distance away, and Herman Melville's Arrowhead and Hancock Shaker Village also nearby.
This apartment offers accommodation for up to four guests, featuring a king-size bed, a sofa bed in the living room, air conditioning, and complimentary Wi-Fi, and is within easy reach of the Berkshire Museum and Bousquet Ski Area.

This seven-bedroom Pittsfield holiday home is conveniently located within a 1.6km walk of the Colonial Theatre, Berkshire Athenaeum, and Berkshire Museum, and under 1.6km from the Housatonic River and Barrington Stage Company.
This spacious 307 square metre property sleeps nine guests and boasts a fully equipped kitchen, two bathrooms, laundry facilities, a fireplace, terrace, garden, and parking, all within easy reach of Pittsfield's cultural attractions and transport links.

This family-friendly villa is situated in a peaceful rural setting in Lenox, just 1.6 km from Ventfort Hall Mansion and Gilded Age Museum, The Bookstore, and Shakespeare and Company. The property has received excellent ratings for user experience, location, and cleanliness.
This spacious 1,394 square metre property offers 13 bedrooms and 13.5 bathrooms. Enjoy the convenience of a fully equipped kitchen, a fitness centre, a sauna, a tennis court, and a garden with barbecue facilities.

This two-bedroom apartment, situated in The Ponds at Foxhollow in the Berkshires, Massachusetts, is conveniently located 4.7km from The Mount, 11.6km from the Norman Rockwell Museum, and 6.9km from Tanglewood.
The property, sleeping up to six guests, boasts a fully equipped kitchen, three bathrooms, a private deck with scenic pond views, resort access to pools, a fitness centre, and a sauna, plus on-site parking.

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 newly refurbished lakefront property in Lenox offers direct access to Laurel Lake, with a private dock for swimming and kayaking, and is within walking distance of The Mount.
This spacious 200 square metre residence accommodates up to 10 guests across four bedrooms and three bathrooms, featuring a modern chef's kitchen, a wood-burning fireplace, a sunroom with a foosball table, and is conveniently located near Tanglewood and ski resorts.

This exclusive lakeside estate in Lenox, Massachusetts, offers private lake access and is within walking distance of The Mount, Edith Wharton’s Home, and a short drive from Tanglewood.
This expansive property comprises two homes, accommodating up to 18 guests with eight bedrooms and five bathrooms, featuring a chef's kitchen, separate guest house, and ample parking for eight vehicles.

This Lenox flat offers immediate access to local attractions, situated within walking distance of The Bookstore and Lenox Library, and a short distance from Ventfort Hall Mansion and Gilded Age Museum and the Berkshire Scenic Railway Museum.
This accommodation provides a fully equipped kitchen, air conditioning, on-site parking, and in-unit laundry, ensuring a comfortable stay with internet access and television for entertainment.

This secluded mountain holiday home in rural West Stockbridge offers convenient access to the Tanglewood Music Centre, just a 6-minute drive away, and the Hotchkiss Mobile Studio, a 5-minute drive.
Spanning 584 square metres, this expansive property accommodates up to 12 guests with six bedrooms and five bathrooms, featuring a private heated swimming pool, a barbecue area, complimentary Wi-Fi, and a cosy fireplace.