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Lenox, MA vacation rentals
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Best Vacation rentals and Airbnb offers in Lenox, MA

Best Lenox, MA vacation rentals with a balcony

St Anne`s Manor | Walk To Downtown!  Sleeps 8 - Lenox, MA
10 127 reviews

St Anne`s Manor | Walk To Downtown! Sleeps 8

apartment, Lenox
This five-bedroom, three-bathroom Victorian home in downtown Lenox, Massachusetts, is a three-block walk from the bus station and within walking distance of numerous restaurants and shops.
This spacious rental boasts a well-equipped eat-in kitchen, a private backyard with a terrace and gas grill, and parking for three cars (shared driveway, plus street parking April 1st-November 1st), comfortably accommodating larger groups near Kennedy Park, Ventfort Hall, The Mount, and Arrowhead.
General Williams Estate House Lenox/stockbridge - Lenox, MA
9.8 120 reviews

General Williams Estate House Lenox/stockbridge

apartment, Stockbridge
This spacious Stockbridge estate, two miles from Stockbridge Center and five miles from Lenox Center, offers easy access to the Mass Pike and Berkshire attractions.
The 5,500-square-foot home boasts six bedrooms, six bathrooms, and accommodates up to sixteen guests, featuring two kitchens, a pool, a spa, and ample outdoor space perfect for family gatherings or group retreats.
Berkshires Mid-century Retreat! - Lenox, MA
No reviews

Berkshires Mid-century Retreat!

apartment, West Stockbridge
This West Stockbridge residence offers a unique mountain setting on 14 acres at the end of a dead-end road, providing immediate access to hiking trails just 2 minutes away and exceptional proximity to Tanglewood and Kripalu, both 5 minutes away. This 5-bedroom, 3-bathroom rental features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, terrace, garden, sauna, and parking, located 15 minutes from wineries, 10 minutes from museums, and 20 minutes from skiing.
Spacious Lenox Home Near Tanglewood - Lenox, MA
No reviews

Spacious Lenox Home Near Tanglewood

apartment, Lenox
This Lenox vacation home offers a prime location, just a 6-minute drive from Tanglewood Music Center and within walking distance of Wyndhurst Golf & Club.
This 2640 sq ft residence accommodates up to 12 guests with 4 bedrooms and 3 bathrooms, featuring a full kitchen, air conditioning, Wi-Fi, a fireplace, and outdoor living spaces including a garden and barbecue area.

Search Family Vacation Rentals in Lenox, MA

Lenox, MA family-friendly vacation rentals provide a perfect base for outdoor adventure.

Artist's Camp On Lake Mahkeenac - Lenox, MA
9.6 22 reviews

Artist's Camp On Lake Mahkeenac

cabin, Stockbridge
This cabin rental in Stockbridge is situated on a river, offering a unique and serene setting with a private garden and barbecue grills. It is within 3 miles of renowned cultural and historical attractions, including Frelinghuysen Morris House and Studio, Tanglewood Music Center, The Mount, Naumkeag Museum, and Berkshire Botanical Garden.
The cabin has an excellent user rating and can accommodate up to 4 guests with 2 bedrooms and 1 bathroom. It features a cozy fireplace, a fully equipped kitchen, a spacious dining area, a private patio, a Smart TV, and a washing machine for added convenience. Guests can also enjoy air conditioning, a terrace or balcony, a garden, a spa, and parking.
Hip Stockbridge Cabin - A Stroll To The Lake - Lenox, MA
9.8 254 reviews

Hip Stockbridge Cabin - A Stroll To The Lake

cabin, Stockbridge
This Stockbridge cabin is located in a serene lake neighborhood with a charming bohemian interior, just steps away from the picturesque Stockbridge Bowl. It has excellent user, location, and cleanliness ratings.
The cabin has a floor area of 900 square feet and can accommodate up to 6 guests. It features a cozy sleeping loft, a reading nook, and a fieldstone fireplace. The spacious yard, sunny deck, and outdoor amenities make it perfect for relaxation and outdoor entertainment.
The Ponds At Foxhollow - Lenox, MA
8.0 332 reviews

The Ponds At Foxhollow

resort, Lee
The Ponds at Foxhollow By Capital Vacations is located in Lenox, Massachusetts, just 2.5 miles from the renowned Tanglewood music venue. The resort has received very good user ratings, with excellent ratings for its location and very good ratings for cleanliness.
The resort offers a variety of accommodations, including villas and apartments. Guests can enjoy a range of amenities, including indoor and outdoor pools, a fitness center, a sauna, and free bicycle rentals.
Visit Us 3 Minutes From Tanglewood Music Hall And Kripalu Yoga Center - Lenox, MA
No reviews

Visit Us 3 Minutes From Tanglewood Music Hall And Kripalu Yoga Center

apartment, Lenox
This Lenox apartment is located a 3-minute drive from Housatonic River and a 5-minute drive from Guido's Marketplace, offering convenient access to local attractions.
This 1000-square-foot condo features one bedroom, one bathroom, air conditioning, and a full kitchen, with parking available and proximity to Jiminy Peak Mountain Resort and Kennedy Park.

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Best Lenox, MA vacation rentals with a fireplace

Classic Stockbridge Cottage - Lenox, MA
10 19 reviews

Classic Stockbridge Cottage

apartment, Stockbridge
This charming cottage is located in a quiet Stockbridge neighborhood, just a short walk from Chesterwood and the Rockwell Museum, and a quick drive to Tanglewood and the Berkshire Botanical Garden. It has received excellent user ratings and is perfect for families or groups of friends looking for a comfortable and spacious vacation home.
The cottage offers 2,770 square feet of living space with four bedrooms and three bathrooms, comfortably accommodating up to eight guests. Amenities include a fully equipped kitchen, central air conditioning, a washer and dryer, and a large outdoor terrace with plenty of space for relaxing and dining.
Classic Stockbridge Cottage - Lenox, MA
No reviews

Classic Stockbridge Cottage

house, Stockbridge
This Stockbridge cottage, a 19-minute walk from the Norman Rockwell Museum and six miles from Tanglewood, offers convenient access to Stockbridge's cultural attractions.
This 2770-square-foot home features four bedrooms, three bathrooms, sleeps eight guests, and includes amenities such as a fully equipped kitchen, air conditioning, Wi-Fi, and a private garden with parking.
Fall Weekends And Ski Season Is Here! - Lenox, MA
9.6 11 reviews

Fall Weekends And Ski Season Is Here!

house, Stockbridge
This Stockbridge apartment is conveniently located just two miles from Tanglewood, less than five minutes from Stockbridge Town Beach, and five minutes from downtown Stockbridge. The apartment consistently receives excellent ratings for location, cleanliness, and overall user experience.
This three-bedroom, two-bathroom home comfortably sleeps six guests. You’ll enjoy modern amenities like a fully equipped kitchen, laundry facilities, high-speed internet, and a cozy fireplace, along with outdoor spaces like a sun deck with a fire pit and a spacious backyard.
Peaceful 1br Condo With Pond View - Lenox, MA
8.8 3 reviews

Peaceful 1br Condo With Pond View

apartment, Lenox
This Lenox condo, near The Mount and Frelinghuysen Morris House & Studio museums and Pleasant Valley Wildlife Sanctuary, offers a peaceful retreat for exploring Berkshire County's cultural and natural attractions.
This one-bedroom, two-bathroom apartment sleeps four and features pond views, providing a tranquil setting for a relaxing getaway near the Bookstore and Berkshire Scenic Railway Museum.

Best Lenox, MA vacation rentals with a sauna

Condo ∙ 2 Bedrooms ∙ 6 Guests - Lenox, MA
No reviews

Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Lenox
This Lenox, Massachusetts condo rental is conveniently located in the Berkshires, a short drive from The Mount (2.9 miles), Norman Rockwell Museum (7.2 miles), and Tanglewood (4.3 miles).
This two-bedroom, three-bathroom vacation home sleeps six guests and boasts a fully equipped kitchen, private deck with scenic pond views, access to resort amenities including indoor/outdoor pools, a fitness center, and a sauna.

Choose the Right Luxury Vacation Rentals in Lenox, MA

For a top-tier experience, choose a luxury vacation rental in Lenox, MA that delivers on every front.

Urban Peak Escape, Lenox, Ma - Lenox, MA
8.0 1 review

Urban Peak Escape, Lenox, Ma

apartment, Lenox

Guest-Favorite Pet-Friendly Vacation Rentals in Lenox, MA

These dog-friendly vacation rentals and Airbnbs in Lenox, MA offer vast space and easy access to local hiking trails.

Fall Weekends And Ski Season Is Here! - Lenox, MA
No reviews

Fall Weekends And Ski Season Is Here!

apartment, Stockbridge
Scroll No More - Your Magical Lenox Place - Lenox, MA
10 7 reviews

Scroll No More - Your Magical Lenox Place

apartment, Lenox
Hawthorne House - Lenox, MA
10 2 reviews

Hawthorne House

apartment, Stockbridge
Classic New England Home With A Swimming Pool - Lenox, MA
9.9 17 reviews

Classic New England Home With A Swimming Pool

apartment, Richmond

Top-Rated Vacation Rentals with Swimming Pool in Lenox, MA

Enjoy a refreshing swim at your convenience with these Lenox, MA vacation rentals featuring on-site pools.

Classic New England Home With A Swimming Pool - Lenox, MA
9.9 17 reviews

Classic New England Home With A Swimming Pool

apartment, Richmond
Berkshires Mid-century Retreat! - Lenox, MA
No reviews

Berkshires Mid-century Retreat!

apartment, West Stockbridge
Tranquil Lakeside Escape In The Berkshires - Lenox, MA
8.8 3 reviews

Tranquil Lakeside Escape In The Berkshires

apartment, Lenox
Peaceful 1br Condo With Pond View - Lenox, MA
8.8 3 reviews

Peaceful 1br Condo With Pond View

apartment, Lenox

Discover Vacation Rentals with Jacuzzi in Lenox, MA

Nothing beats coming home to a hot tub after a day of hiking in Lenox, MA.

Berkshires Chalet Mins To Tanglewood/lenox - Lenox, MA
9.7 6 reviews

Berkshires Chalet Mins To Tanglewood/lenox

apartment, Richmond
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