Holiday Rentals in Lenox, MA

The Gatehouse on Golden Hill is a 4-bedroom house located in Lee, Massachusetts, just 7.2 kilometres from Tanglewood and 8 kilometres from the Norman Rockwell Museum, offering easy access to cultural attractions and the natural beauty of the Berkshires. The house has received excellent ratings for location, cleanliness, and overall user experience.
The property spans 279 square metres and comfortably accommodates up to 10 guests. The house features a fully equipped kitchen, air conditioning, free Wi-Fi, and parking, along with access to nearby amenities like the Cranwell Spa & Golf Club and opportunities for skiing and cycling.

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 West Stockbridge holiday home, minutes from Tanglewood, Kripalu Centre for Yoga & Health, Lenox and Stockbridge town centres, and the Norman Rockwell Museum, offers convenient access to Berkshire attractions.
The 279-square-metre (approx. 3000 sq ft) property boasts five bedrooms, three bathrooms, sleeps eight guests, and includes a fully equipped kitchen, spa, garden, parking, and numerous amenities such as satellite TV and Netflix.

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 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.

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 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 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 Lenox condo, a short 6.4km drive from The Mount and 9.6km from the Housatonic River, offers convenient access to local attractions.
The two-bedroom, three-bathroom apartment sleeps six, boasting a fully equipped kitchen, in-unit laundry, a swimming pool, sauna, parking, and free Wi-Fi.

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.

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 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 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 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.

This charming house in Stockbridge is just a short drive from Lee Premium Outlets, Lenox Center, and Canyon Ranch, placing you near a range of attractions and shopping opportunities. The house has consistently received excellent ratings for its cleanliness, location, and overall guest experience.
The property offers a private entrance and separate living space for up to four guests. It features a fully equipped kitchen, modern appliances, a private porch, and a garden, making it a comfortable and convenient option for your stay.