Holiday Rentals in Lenox, MA

This charming one-bedroom flat is located in downtown Lenox, just 1.9 kilometres from the renowned Tanglewood music venue and within easy walking distance of shops, restaurants, and the town’s vibrant atmosphere. It boasts excellent ratings for location, cleanliness, and overall user experience.
The flat offers a comfortable space for two guests, with a well-equipped kitchen, air conditioning, and parking. Enjoy a convenient location, a charming French bakery across the street, and explore Lenox on foot, taking advantage of the nearby attractions and amenities.

This two-bedroom apartment is situated on Main Street in the centre of Lenox, just a short walk from the Tanglewood Music Center and the numerous shops and restaurants of the town.
The apartment offers keyless entry, a fully equipped kitchen, a comfortable living space with a Smart TV, and a spacious dining area, making it ideal for families or groups of up to six guests.

This two-bedroom cottage is situated just 1.4 kilometres from the Tanglewood music venue and 2.4 kilometres from the Kripalu Centre for Yoga and Health, placing it within easy reach of Lenox's cultural highlights. The property offers a fully equipped kitchen with a fridge, freezer, microwave oven and dishwasher, as well as a garden, parking and air conditioning for a comfortable stay.

This Lenox cottage, a short 0.5km walk downhill from Lenox town centre and a similar distance uphill from Kennedy Park, offers easy access to restaurants, shops, and the park.
The one-bedroom, one-bathroom property sleeps three, features a full kitchen, in-unit laundry, free Wi-Fi, and a stereo/record player, plus a piano; dogs are welcome (fee applies).

This Lenox apartment, newly renovated and located in the town centre, offers easy access to attractions such as Ventfort Hall Mansion and the Shakespeare & Company bookshop.
The one-bedroom flat sleeps four guests, features a fully equipped kitchen with dishwasher, and includes high-speed Wi-Fi, parking and air conditioning.

The Willow Suite, a renovated 1800s carriage house on a 50-acre Shaker farm near East Nassau, New York, offers easy access (15-40 minutes' drive, or 24-64km) to Berkshires and Hudson River Valley attractions including Tanglewood.
This self-catering holiday home features a king-size and single bed, sleeping up to five guests, a full kitchen with dishwasher, air conditioning, high-speed Wi-Fi, and access to walking paths, a shared grill, and fire pit on the property.

This two-bedroom apartment is situated in a central Lenox location, just a short distance from October Mountain and close to the town's main attractions.
The apartment is newly renovated and offers a comfortable living space for up to six guests, with amenities such as a fully equipped kitchen, a dining room, a living room, and off-street parking.

This log cabin, nestled in the district of Monterey bordering Tyringham, is located within a short drive of attractions like Greenock Country Club, Otis Ridge, Ashintully Gardens, and Berkshire Scenic Railway Museum. This secluded dwelling, situated on 35+ acres of woodland, offers a peaceful retreat with stunning views of the Tyringham Valley, a spacious living area with vaulted ceilings and a fireplace, a modern kitchen, a screen porch with a hot tub, and a wraparound deck.

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 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 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.

Lenox Hills Cottage is a rustic cabin located in the Berkshires, just a few kilometres from Tanglewood, Kennedy Park, and Lenox town centre, offering a tranquil escape in the heart of nature. The cottage has received excellent ratings for its location, cleanliness, and overall experience.
The property has two bedrooms and two bathrooms, accommodating up to four guests. Amenities include a fully equipped kitchen, a wood-burning fireplace, a screened sunroom with a hammock, and a wraparound porch for enjoying al fresco dining, as well as a garden and parking for two to three cars.

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 Berkshires farmhouse, near Lenox, Massachusetts, is situated 14.5km from Tanglewood and a short drive from Stockbridge.
The 2000+ sq ft property boasts three bedrooms, two bathrooms, sleeping seven guests, and features a large open-plan living area, a fully equipped kitchen including a dishwasher, and outdoor amenities such as a BBQ and fire pit.

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 charming bungalow is situated in the city centre of Pittsfield, just 5km from Bousquet Ski Resort, 20km from Jiminy Peak and 15km from Tanglewood in Lenox, offering easy access to the area's attractions. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The home sleeps up to 5 guests and spans 93 square metres. It features a fully equipped kitchen, a spa, air conditioning and a private deck with a grill, perfect for enjoying the outdoors.

This one-bedroom flat in Pittsfield is conveniently situated, a mere 3-minute drive from both the Colonial Theatre and the Berkshire Museum, placing you in prime position to explore the town and the wider Berkshire region.
This comfortable flat accommodates up to four guests and includes essential amenities such as air conditioning, on-site laundry facilities with a washing machine and dryer, and provided linens and towels for a convenient stay.

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.

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.

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 apartment is located in The Ponds at Foxhollow Resort in Lee, Massachusetts, just a short drive (around 10 kilometres) from Lenox and the Tanglewood Music Center. The surrounding area is known for its picturesque scenery, offering stunning views of a pond and the Berkshire mountains.
The apartment has a master bedroom with a king-sized bed, a master bathroom with a jacuzzi, a fully equipped kitchen, a dining area, a living space with a double sleeper sofa, and a loft sitting room, comfortably accommodating up to six guests. Guests have access to a wide range of amenities, including swimming pools, a hot tub, a sauna, an exercise room, a library, and a business centre, as well as outdoor activities such as tennis courts, a putting green, and hiking trails.

This Lenox, Massachusetts apartment, situated in the Ponds at Foxhollow, is conveniently located 7km from Tanglewood, 11.6km from the Norman Rockwell Museum, and 4.6km from Edith Wharton's The Mount.
The self-catering condo offers one bedroom, two bathrooms, sleeps four guests, and features a fully equipped kitchen, private deck with pond views, indoor/outdoor pools, a fitness centre, sauna, and free Wi-Fi.

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, 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 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 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 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 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.