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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

Stunning Post & Beam Home Minutes From Lenox, Stockbridge And Tanglewood! - Lenox, MA
10 99 reviews

Stunning Post & Beam Home Minutes From Lenox, Stockbridge And Tanglewood!

apartment, Lee
This vacation home in Lee is located close to a lake, within a mile of Greenock Country Club and the Housatonic River, offering a peaceful escape near local attractions. It has received excellent user ratings, making it a popular choice for travelers.
The home features five bedrooms, four bathrooms, and can comfortably accommodate up to 14 guests in its 2800 square feet of space. Amenities include a fully equipped kitchen, a fireplace, a fitness center, a spa, a garden, a terrace, and parking, ensuring a comfortable and enjoyable stay.
Built For A Us Secretary Of State 13k Sf In Lenox - Lenox, MA
10 68 reviews

Built For A Us Secretary Of State 13k Sf In Lenox

house, Lenox
This family-friendly villa is located in a peaceful rural area of Lenox, just a short walk from Ventfort Hall Mansion and Gilded Age Museum, The Bookstore, and Shakespeare and Company, with Tanglewood Music Center a short drive away. The property has received excellent ratings for user experience, location, and cleanliness.
The spacious home spans 15,000 square feet and features 13 bedrooms, a fully equipped kitchen, a fitness center, a sauna, a tennis court, a garden, and a terrace. Guests can enjoy a range of activities, including exploring the nearby cultural landmarks, relaxing in the peaceful surroundings, or enjoying a game of tennis.
Amore Estate -  Beautiful Room With Many Places To Explore And Relax In. - Lenox, MA
9.2 39 reviews

Amore Estate - Beautiful Room With Many Places To Explore And Relax In.

apartment, Lenox
This 6-bedroom apartment is located in Lenox, just a mile from the Lenox Center and 1.5 miles from Tanglewood, offering easy access to cultural events and attractions. Guests consistently rate this rental as excellent, praising its privacy, stunning views, and peaceful atmosphere.
This spacious home can comfortably accommodate up to 16 guests and features a wrap-around porch, a swimming pool, a sports court, and a garden. Guests can also enjoy fresh eggs from the on-site chickens and take advantage of the nearby hiking trails and natural beauty.
General Williams Estate House Lenox/stockbridge - Lenox, MA
9.8 117 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.

Search Family Vacation Rentals in Lenox, MA

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

Stockbridge Cape Near Tanglewood! - Lenox, MA
10 115 reviews

Stockbridge Cape Near Tanglewood!

apartment, Stockbridge
This lakefront vacation rental is just a short drive from the Berkshire Botanical Garden and Tanglewood Music Center, offering easy access to Stockbridge's cultural attractions. The home has earned excellent ratings for location, cleanliness, and overall guest experience.
This 4-bedroom, 2-bathroom home comfortably sleeps 7 guests in its 1640 square feet of living space. Enjoy lake views, a private patio, barbecue grills, a fully equipped kitchen, and a fireplace for cozy evenings.
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.
Friendly Hills | Passive Home  Ev Charger - Lenox, MA
9.8 37 reviews

Friendly Hills | Passive Home Ev Charger

apartment, Hancock
This mid-century modern apartment rental near Hancock Shaker Village in Hancock, Massachusetts offers panoramic views and private access to hiking trails and ponds on six acres.
The three-bedroom, two-bathroom unit sleeps six guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, plus fast Wi-Fi, air conditioning, and parking.
Lake View Berkshires Retreat - Private & Minutes To Lenox - Lenox, MA
10 30 reviews

Lake View Berkshires Retreat - Private & Minutes To Lenox

apartment, Lee
This Lee, Massachusetts lakeside home is located within two miles of the Berkshire Mountain Country Store, Housatonic River, Greenock Country Club, Wyndhurst Golf & Club, and the Animagic Museum of Animation.
This 3160-square-foot vacation rental boasts five bedrooms, four bathrooms, sleeps fourteen guests, and features a fully equipped kitchen, Jacuzzi, spa, tennis court, and a terrace overlooking the lake.

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Best Lenox, MA vacation rentals with a fireplace

Seeking "School Year" Sept-june. Please Inquire! - Lenox, MA
9.6 11 reviews

Seeking "School Year" Sept-june. Please Inquire!

apartment, 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.
Comfy Modern  Convenient Location  2br Queen Bed - Lenox, MA
9.4 97 reviews

Comfy Modern Convenient Location 2br Queen Bed

apartment, Stockbridge
This ground-floor condo in Stockbridge is conveniently located just minutes from Kripalu Center for Yoga & Health, Tanglewood, and Stockbridge Bowl, offering easy access to popular attractions. The property consistently receives excellent ratings for its cleanliness, location, and overall guest experience.
This comfortable apartment features two bedrooms and one bathroom, comfortably accommodating up to six guests. The well-equipped kitchen includes a dishwasher and washer/dryer, while the spacious yard provides a private outdoor area with a BBQ grill.
Berkshires Colonial On 2 Acres By Evergreen Home - Lenox, MA
10 7 reviews

Berkshires Colonial On 2 Acres By Evergreen Home

apartment, Richmond
This 4-bedroom home is located in a quiet neighborhood in Richmond, MA, just minutes away from popular Berkshires attractions like Tanglewood, wineries, and ski resorts. It has an excellent user rating and is perfect for families or groups of up to 10 guests.
The spacious home features a dedicated office space, a large backyard with a fire pit, and a screened-in porch with an additional dining area. Guests can enjoy modern comforts like central AC, a washer and dryer, Wi-Fi, and an EV charger.
Stockbridge Home: Walk To Town Beach! - Lenox, MA
9.9 52 reviews

Stockbridge Home: Walk To Town Beach!

house, Stockbridge
This house is located in Stockbridge, a short distance from Tanglewood and within walking distance of the town beach, making it a convenient base for exploring the area. The house has earned excellent ratings for its location, cleanliness, and overall experience.
The home spans 1040 square feet and has three bedrooms, comfortably accommodating up to six guests. The house offers a range of amenities, including a fully equipped kitchen, air conditioning, a terrace, a spa, and parking, ensuring a comfortable and enjoyable stay.

Best Lenox, MA vacation rentals with a sauna

Spacious 5-bedroom House In Charming Lee With Wifi - Lenox, MA
8.8 3 reviews

Spacious 5-bedroom House In Charming Lee With Wifi

apartment, Lee
Lee Manor, a five-bedroom, four-bathroom house in Lee, Massachusetts, is conveniently located five minutes from Lee Premium Outlets and High Lawn Farm, and within walking distance of downtown Lee and Joe's Diner.
This 15-guest home rental boasts a fully equipped kitchen, Wi-Fi, and proximity to Tanglewood, the Norman Rockwell Museum, and numerous Berkshires attractions, making it perfect for families and groups exploring the area.
Tranquil Lakeside Escape In The Berkshires - Lenox, MA
10 1 review

Tranquil Lakeside Escape In The Berkshires

apartment, Lenox
This Lenox condo is conveniently located near Edith Wharton's The Mount (a 4-minute drive) and the Housatonic River (a 6-minute drive), offering easy access to Lenox's cultural attractions. This two-bedroom, three-bathroom apartment sleeps six and boasts a fully equipped kitchen, in-unit laundry, a swimming pool, sauna, and on-site parking.
The Ponds At Foxhollow - Lenox, MA
8.2 326 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.
Tranquil Lakeside Escape In The Berkshires - Lenox, MA
9.2 22 reviews

Tranquil Lakeside Escape In The Berkshires

apartment, Lee
This apartment is located in The Ponds at Foxhollow Resort in Lee, Massachusetts, close to Tanglewood, a world-renowned music venue, and the town's shops and restaurants. The resort sits in the picturesque Berkshire Mountains, near a scenic pond.
The apartment comfortably accommodates up to six guests in three bedrooms, including a master bedroom with a king-sized bed, a second bedroom with a queen-sized bed, and a living space with a double sleeper sofa. This apartment offers access to resort amenities such as indoor and outdoor pools, hot tubs, saunas, an exercise room, tennis courts, a putting green, and a variety of outdoor sports equipment.

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.

Charming Downtown Lenox Getaway At 30 Franklin - Lenox, MA
10 3 reviews

Charming Downtown Lenox Getaway At 30 Franklin

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.

Lenox Grand Colonial With Pool By Evergreen Home - Lenox, MA
10 3 reviews

Lenox Grand Colonial With Pool By Evergreen Home

apartment, Lenox
Stylish Mid-century Modern Berkshires Cape - Lenox, MA
9.9 142 reviews

Stylish Mid-century Modern Berkshires Cape

apartment, Lee
The Belden House - Walk To Tanglewood ! - Lenox, MA
No reviews

The Belden House - Walk To Tanglewood !

apartment, Lenox
Berkshires Sanctuary With Outdoor Living Area & Firepit. 8minutes To Tanglewood! - Lenox, MA
10 15 reviews

Berkshires Sanctuary With Outdoor Living Area & Firepit. 8minutes To Tanglewood!

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.

Peaceful 1br Condo With Pond View - Lenox, MA
9.5 11 reviews

Peaceful 1br Condo With Pond View

apartment, Lee
Berkshire Mountain Retreat - Lenox, MA
9.9 47 reviews

Berkshire Mountain Retreat

studio, Richmond
Luxury Fox Hollow Estate Home On Laurel Lake - Dream Location, Hot Tub, Kayaks++ - Lenox, MA
9.4 65 reviews

Luxury Fox Hollow Estate Home On Laurel Lake - Dream Location, Hot Tub, Kayaks++

apartment, Lee
Berkshire Mountain Lodge - Lenox, MA
8.8 1668 reviews

Berkshire Mountain Lodge

house, Pittsfield

Discover Vacation Rentals with Jacuzzi in Lenox, MA

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

3 Acres, Mtn Views, Hot Tub, Steps To Winery - Lenox, MA
No reviews

3 Acres, Mtn Views, Hot Tub, Steps To Winery

apartment, Richmond
Hideaway In The Woods - Lenox, MA
9.8 28 reviews

Hideaway In The Woods

apartment, Stockbridge
3 Acres, Mtn Views, Hot Tub, Steps To Winery - Lenox, MA
No reviews

3 Acres, Mtn Views, Hot Tub, Steps To Winery

apartment, Richmond
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