Holiday Rentals in Lenox, MA

This historic country home, a National Historic Landmark built in 1881, is located on a 15-hectare hilltop in Lenox, offering a peaceful rural escape within walking distance to Tanglewood and a 3-minute drive to downtown Lenox and Stockbridge Bowl.
This 6-bedroom property accommodates up to 10 guests and features a chef's kitchen with a Viking stove, a music parlour with a vintage Steinway grand piano, a dedicated yoga and meditation room, a home office, air conditioning, a garden, a fitness centre, and a veranda.

This Lee holiday let is conveniently situated less than 1 kilometre from the Mass Pike exit, offering easy access to Lee Premium Outlets and recreational pursuits such as skiing, hiking, and golf at Greenock Country Club and Wyndhurst Golf & Club.
This 4-bedroom, 2-bathroom apartment accommodates up to 9 guests and features a well-equipped kitchen, outdoor grilling area, swimming pool, and garden, with well-behaved pets considered on a case-by-case basis.

This Lenox property is located just six kilometres from both Cranwell Spa & Golf Club and Tanglewood Musical Center, making it a convenient base for exploring the area's cultural and leisure attractions. The house has received excellent ratings for cleanliness and user experience, and a very good rating for its location.
The three-bedroom house offers 228 square metres of space and can comfortably accommodate up to six guests. The property features a fully equipped kitchen, air conditioning, a garden, a spa, parking, and free Wi-Fi, ensuring a relaxing and enjoyable stay.

This Lenox holiday home is situated in a rural setting, less than 3km from the Housatonic River and the historical Arrowhead, home of Herman Melville.
This four-bedroom, three-bathroom property boasts 281 square metres of living space, a private pool, barbecue facilities, and sleeps eight guests, offering free Wi-Fi and a fully equipped kitchen.

This Lenox holiday home, near the beach and a 2.4km walk from Wyndhurst Golf & Club and The Mount, offers easy access to local attractions including Shakespeare and Company and Ventfort Hall Mansion within 5km.
The 176 square metre property boasts four bedrooms, two bathrooms, sleeping up to ten guests, and features a fully equipped kitchen, private balcony, garden, parking, and internet access.

This charming cottage is located in a quiet neighbourhood in Stockbridge, just a short walk from Chesterwood and the Rockwell Museum, and a short drive to Tanglewood, Berkshire Botanical Garden, and Stockbridge Bowl. The cottage has received excellent reviews from previous guests.
The property has four bedrooms and three bathrooms across 257 square metres, comfortably accommodating up to eight guests. This charming retreat features a well-equipped kitchen, a spacious living room with a fireplace, a library, a dedicated lounge area, and a private garden.

This fully renovated house is located on a quiet street in Lee, Massachusetts, just a short drive from both Lee Center and Lenox Center, offering a peaceful retreat in a convenient location. It has received excellent ratings for user experience, location, and cleanliness.
The spacious property spans 260 square metres and comfortably accommodates up to 11 guests across five bedrooms and three bathrooms. Guests can enjoy a well-equipped kitchen, a family room with a pool table, a terrace, a garden, parking, and air conditioning, making it perfect for families and groups seeking a comfortable and enjoyable stay.

This family-friendly holiday home is situated near the lake in Lee, within a mile of Greenock Country Club and the Housatonic River, and within two miles of the Animagic Museum of Animation and Lee Library. This property enjoys excellent user ratings, making it a popular choice for travellers visiting Lee.
The house has 5 bedrooms, 4 bathrooms, and a floor area of 260 square metres, comfortably accommodating up to 14 guests. Amenities include a fully equipped kitchen, a fireplace, a terrace, a garden, a fitness centre, and a spa, ensuring a comfortable and enjoyable stay.

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 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.

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 Stockbridge flat is located moments from the Norman Rockwell Museum and Tanglewood, offering easy access to local points of interest and natural landscapes, with the Berkshire Botanical Garden a mere 200 meters away.
This spacious 218 square meter residence features 3 bedrooms and 2.5 bathrooms, accommodating up to 6 guests with amenities including Wi-Fi, air conditioning, a garden, sauna, and parking.

This apartment is located in Stockbridge, just 6 kilometres from Tanglewood and Lenox, offering a peaceful retreat in the picturesque Berkshires. With excellent user, location, and cleanliness ratings, this property promises a comfortable and enjoyable stay.
The apartment is a spacious home with 3 bedrooms and 2 bathrooms, comfortably accommodating up to 7 guests. The property features a fully equipped kitchen, a dedicated office space, a large outdoor deck, a hot tub, a fire pit, a swingset, and a washer and dryer, ensuring a relaxing and enjoyable experience for all.

This charming cottage is located on a river, just 3.4 kilometres from the Frelinghuysen Morris House and Studio and 3.8 kilometres from Tanglewood Music Center, making it a great base for exploring Stockbridge's cultural attractions. It has received excellent reviews from previous guests.
The property has two bedrooms and one bathroom, comfortably accommodating up to four guests. The cottage is equipped with a fully equipped kitchen, a terrace, a garden, a fireplace, and a spa, offering a comfortable and relaxing stay.

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 Lenox property is situated in a peaceful residential area, a short walk from Lenox village centre and its amenities, with Kennedy Park and Tanglewood within easy reach.
The two-bedroom, two-bathroom house sleeps six guests and boasts a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, a garden, parking, and is rated excellent for cleanliness, location and overall user experience.