Holiday Rentals in Lenox, MA

This Lenox guesthouse, situated on a 10-acre estate a 1.6km walk from the town centre, is 1.6km from Tanglewood and Shakespeare & Company, and 22.5km from Jacob's Pillow.
The self-catering property offers one bedroom, one bathroom, sleeping two guests, and boasts a fully equipped kitchen, high-speed Starlink internet, and a private garden with stunning sunset views; nearby Kennedy Park provides hiking and biking opportunities.

This family-friendly Lenox flat offers a prime central downtown location, placing you within easy walking distance of numerous acclaimed Lenox restaurants and attractions, and serving as an excellent base for exploring the Berkshires' natural and cultural offerings.
This updated accommodation sleeps six across three bedrooms and two bathrooms, featuring a spacious backyard patio and lawn, and providing modern comforts including air conditioning, Wi-Fi, and a fully equipped kitchen with a dishwasher and microwave, alongside convenient parking.

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 detached house in Lenox is situated 2.7 kilometres from Cranwell Spa & Golf Club and 5.9 kilometres from Tanglewood Musical Center, with Great Falls and Canaan Village Historic District both 40.2 kilometres away.
This property accommodates up to 18 guests with 1 bedroom, 5 bathrooms, air conditioning, a kitchen, free Wi-Fi, private parking, and a garden, offering an ideal setting for family gatherings near the Norman Rockwell Museum.

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.

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 three-bedroom split ranch in Lenox is located directly beside October Mountain State Forest, offering immediate access to nature and a short drive to Lenox town centre and its cultural attractions including Tanglewood and the Norman Rockwell Museum.
This family-friendly property sleeps six guests and features a kitchen with a fridge, microwave, and dishwasher, air conditioning, and internet access, with nearby opportunities for hiking, biking, kayaking, and fishing.

This modern A-frame cabin is located in Lenox, just a short walk from Tanglewood, Kennedy Park, and Kripalu, offering easy access to cultural events, outdoor recreation, and wellness activities. The property has consistently received excellent ratings for location, cleanliness, and overall guest experience.
The cabin features a split-level mezzanine design, offering a blend of modern and rustic charm, and can accommodate up to six guests. Enjoy stunning views of the Berkshires from the open living room with triple-height ceilings, relax on the sun porch or deck, or unwind in the garden hammocks. The cabin also includes a fully equipped kitchen, a private garden, a ping pong table, and BBQ facilities available upon request.

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 Richmond, Massachusetts studio apartment is situated near the Berkshire High Road Trailhead, less than 0.4 kilometres from miles of hiking and biking trails, and within a short drive of attractions such as Tanglewood and Kripalu.
The self-contained apartment, sleeping up to two guests, boasts a private patio, parking for two cars, a fully equipped kitchenette (fridge, freezer, microwave), air conditioning, and access to a swimming pool and garden; nearby Bartlett's Apple Orchard offers fresh produce.

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 spacious Dutch Gambrel house, situated in Lenox, Massachusetts, is a five-minute drive from Lenox town centre and close to Tanglewood.
Offering 238 square metres of living space, this four-bedroom, 2.5-bathroom property sleeps eight guests and boasts a fully equipped kitchen, large garden with fire pit, and off-street parking; small dogs are welcome (with prior approval and fee).