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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

Amore Estate -  Beautiful Room With Many Places To Explore And Relax In. - Lenox, MA
9.2 40 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.
The Reel Retreat | Theatre & Firepit  Game Room - Lenox, MA
10 6 reviews

The Reel Retreat | Theatre & Firepit Game Room

apartment, Pittsfield
This four-bedroom, two-bathroom Pittsfield vacation rental is located in southern Pittsfield, minutes from downtown Pittsfield and Lenox, providing easy access to Tanglewood and Barrington Stage Company.
The 4-bedroom home boasts a private backyard, a fully equipped kitchen, a dedicated movie theater, a game room, and a deck with a grill, comfortably accommodating up to 7 guests and offering proximity to Bousquet Ski Area, Canoe Meadows, and Kennedy Park.
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.
Spacious Historic Home In The Berkshires! - Lenox, MA
No reviews

Spacious Historic Home In The Berkshires!

cottage, Pittsfield
This Pittsfield cottage boasts a prime location, within a 10-minute walk of the Colonial Theatre, Berkshire Athenaeum, and Berkshire Museum, and less than a mile from the Housatonic River and Barrington Stage Company.
This pet-friendly vacation home features two bathrooms, a fully equipped kitchen with microwave and dishwasher, a private balcony, free Wi-Fi, and free self-parking, plus a fireplace and air conditioning for added comfort.

Search Family Vacation Rentals in Lenox, MA

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

Charming 19th Century Farmhouse - Lenox, MA
10 44 reviews

Charming 19th Century Farmhouse

apartment, Lee
This apartment is located in Lee, MA, within walking distance of restaurants, parks, and shops, and a short drive from cultural attractions like Tanglewood and Jacob's Pillow. It boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The apartment is spacious and comfortable, accommodating up to 5 guests with 3 bedrooms and 2 bathrooms. It offers a range of amenities, including a fully equipped kitchen, air conditioning, a private garden, parking, and pet-friendly accommodations.
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.
Spacious 4br Central-berkshires Home With Pool! - Lenox, MA
10 3 reviews

Spacious 4br Central-berkshires Home With Pool!

apartment, Lee
This Lee apartment is located on a country road, offering peaceful walks and vistas, with convenient access to the Mass Pike exit, Lee Premium Outlets, and attractions like Guido's Marketplace, Greenock Country Club, and Wyndhurst Golf & Club.
This 4-bedroom, 2-bathroom residence accommodates up to 9 guests, featuring a full kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, garden, spa, and parking.
Perfect Location In The Heart Of Downtown Lenox - Lenox, MA
10 3 reviews

Perfect Location In The Heart Of Downtown Lenox

apartment, Lenox
This house is located in Lenox, just a short walk from The Bookstore and a short drive from Tanglewood Music Center. This vacation rental has excellent user ratings, making it a popular choice for travelers.
The house has 3 bedrooms and 3 bathrooms, accommodating up to 6 guests. It offers modern conveniences, a private patio, a garden, and a barbecue grill, making it ideal for a relaxing and enjoyable stay.

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Best Lenox, MA vacation rentals with a fireplace

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.
Berkshires Colonial On 2 Acres By Evergreen Home - Lenox, MA
10 55 reviews

Berkshires Colonial On 2 Acres By Evergreen Home

apartment, Richmond
This spacious 2,624-square-foot colonial house in Richmond, MA, is minutes from Balderdash Cellars and within a 15-minute drive of numerous Berkshires attractions, including Butternut and Catamount ski areas.
The four-bedroom, two-bathroom home sleeps ten and boasts an open-concept kitchen, screened porch, finished basement, a private 2.7-acre lot with a fire pit, and amenities such as a wood-burning fireplace, EV charger, and washer/dryer.
Beautiful Lenox Home, 3 Mi To Shakespeare & Co! - Lenox, MA
9.3 112 reviews

Beautiful Lenox Home, 3 Mi To Shakespeare & Co!

house, Lenox
This Lenox home is located just a short drive from Cranwell Spa & Golf Club, Tanglewood Musical Center, and the Norman Rockwell Museum, offering easy access to all that Lenox has to offer. The property has received excellent ratings for cleanliness, location, and overall user experience. This 3-bedroom home comfortably accommodates up to 6 guests in its 2,450 square feet of living space. Amenities include a fully equipped kitchen, air conditioning, a garden, a spa, parking, and free Wi-Fi.
Serene Lenox Hills Cottage - Berkshires - Lenox, MA
9.6 41 reviews

Serene Lenox Hills Cottage - Berkshires

cabin, Lenox
Lenox Hills Cottage is a cozy 2-bedroom cottage in the heart of the Berkshires, just minutes from popular attractions like Tanglewood and downtown Lenox. With excellent user, location, and cleanliness ratings, this cabin is a great choice for travelers seeking a comfortable and convenient stay.
The cottage features a wraparound porch for outdoor dining, a screened sunroom with a hammock, an indoor wood-burning fireplace, and a fully equipped kitchen. It can accommodate up to four guests comfortably and offers ample parking space. The surrounding wooded area provides privacy and opportunities for outdoor exploration.

Best Lenox, MA vacation rentals with a sauna

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.
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.
Hearth House | Prime Location! - Lenox, MA
10 1 review

Hearth House | Prime Location!

apartment, Stockbridge
This Stockbridge apartment is located minutes from the Norman Rockwell Museum and Tanglewood, offering convenient access to local attractions.
This 2350 square foot residence features 2 bedrooms and 2 bathrooms, accommodating up to 6 guests with a fold-out sofa, and includes a full kitchen, yard with patio, Wi-Fi, air conditioning, and parking.
Spacious 5-bedroom House In Charming Lee With Wifi - Lenox, MA
8.6 4 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.

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.

Luxury 3-bedroom Retreat In Downtown Lenox - Lenox, MA
10 3 reviews

Luxury 3-bedroom Retreat In Downtown Lenox

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.

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

Scroll No More - Your Magical Lenox Place

apartment, Lenox
Spacious Central Berkshires Home For Groups - Lenox, MA
8.0 1 review

Spacious Central Berkshires Home For Groups

apartment, Lee
Friendly Hills | Passive Home  Ev Charger - Lenox, MA
10 3 reviews

Friendly Hills | Passive Home Ev Charger

apartment, Hancock
Imagine Being Lakeside, Kayaks, Fishing, Ev Charger - Lenox, MA
No reviews

Imagine Being Lakeside, Kayaks, Fishing, Ev Charger

house, Lenox

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.

Tranquil Lakeside Escape In The Berkshires - Lenox, MA
10 1 review

Tranquil Lakeside Escape In The Berkshires

apartment, Lenox
The Ponds At Foxhollow - Lenox, MA
8.2 326 reviews

The Ponds At Foxhollow

resort, Lee
Historic Stockbridge Villa On 25 Acres Sleeps 23 - Lenox, MA
10 19 reviews

Historic Stockbridge Villa On 25 Acres Sleeps 23

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

Berkshire Mountain Retreat

studio, Richmond

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

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

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

Berkshire Mountain Lodge

house, Pittsfield
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
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