Holiday Rentals in Lenox, MA

This Lee apartment is conveniently located near the Lee Library, the Animagic Museum of Animation, and the Berkshire Mountain Country Store, with the Housatonic River and Greenock Country Club less than 2.4 kilometres away.
This one-bedroom, one-bathroom flat sleeps four guests and offers a fully equipped kitchen with fridge, microwave, oven and hob, free Wi-Fi, and is a smoke-free environment.

This seven-bedroom farmhouse, sleeping up to eleven guests, is situated in New Lebanon, New York, approximately 2km from the New Lebanon Library, and within 5km of Mount Lebanon Shaker Village and Shatford Memorial Park.
The self-catering property boasts three bathrooms, a fully equipped kitchen including a dishwasher, air conditioning, a terrace, garden, parking, an on-site games room, barbecue facilities, and is conveniently located for exploring Queechy Lake and New Lebanon Town Hall.

This Berkshire County colonial-style house, situated atop a hill overlooking October Mountain, is 11km from Pittsfield and 11km from Lenox, offering easy access to Bousquet Mountain Ski Area.
This 334 square metre property sleeps ten guests in five bedrooms and three bathrooms, boasting a well-equipped kitchen, jacuzzi, fitness centre, and extensive outdoor space including a hot tub, fire pit, and stone patio; additional amenities include a games room with pool table and ping pong table.

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 restored 1881 farmhouse is located in Lenox, just over 5 kilometres from both Tanglewood and Cranwell Spa & Golf Club, in a peaceful rural setting. It has received excellent ratings for location, cleanliness, and overall experience.
The house is a 2-bedroom property with a floor area of 120 square metres, comfortably accommodating up to 4 guests. It offers modern amenities like air conditioning, Wi-Fi, a fully equipped kitchen, a washing machine, and a bathroom with a bath, as well as a terrace and garden for enjoying the outdoors.

This six-bedroom, four-bathroom holiday home in Pittsfield is located a 0.8km walk from the Canoe Meadows Wildlife Sanctuary and a 3.2km drive from the Housatonic River.
The property sleeps fourteen guests and features a fully equipped kitchen with dishwasher and microwave, in-unit laundry, air conditioning, on-site parking, and outdoor barbecue and fireplace facilities; nearby attractions include the Berkshire Museum, Bousquet Ski Area, and the Berkshire Scenic Railway Museum.

This house is located on a lake in Lee, within 2 kilometres of Greenock Country Club, Lee Library, and Animagic Museum of Animation, offering a peaceful retreat in a convenient location. The property has received excellent ratings for user experience, location, and cleanliness.
The property has 4 bedrooms and can accommodate up to 8 guests, providing ample space for families or groups. It features a fully equipped kitchen, a terrace, a garden, and a washing machine, along with air conditioning, internet access, and a Smart TV for entertainment.

This spacious five-bedroom house is situated in Pittsfield, Massachusetts, just 12.2 kilometres from Tanglewood and 12.6 kilometres from Cranwell Spa & Golf Club.
The 307 square metre property offers ample space for up to 17 guests, with modern amenities such as air conditioning, Wi-Fi, a fully equipped kitchen, and a balcony.

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.

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.

Lee Manor, situated in Lee, offers a self-catering holiday home with easy access to local amenities.
This one-bedroom property sleeps up to 35 guests, boasting a fully equipped kitchen, private garden, sauna, bar, free parking, and free Wi-Fi.

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 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 holiday home is located just outside Stockbridge, a short drive from the Berkshire Botanical Garden (2.9 km) and Tanglewood Music Center (4.2 km), offering a peaceful and scenic setting for your stay. The property has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The spacious property spans 152 square metres and comfortably accommodates up to 7 guests in its 4 bedrooms and 2 bathrooms. Guests can enjoy a range of amenities, including a fully equipped kitchen, a garden with barbecue facilities, a private patio, and a spa, making it perfect for relaxing and enjoying the beautiful surroundings.

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 contemporary chalet is located just 7 kilometres from the world-renowned Tanglewood music venue and 1.6 kilometres from the charming town of West Stockbridge, offering a tranquil escape amidst the natural beauty of the Berkshires. The property has received excellent ratings for location, cleanliness, and overall user experience.
The chalet has three bedrooms and two bathrooms, comfortably accommodating up to six guests. This modern retreat features a spacious open floor plan, a fully equipped kitchen, a large den, a private deck, and a laundry room with washer and dryer, providing all the comforts of home for a relaxing and enjoyable stay.