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

Search Family Vacation Rentals in Lenox, MA

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

Stylish Mid-century Modern Berkshires Cape - Lenox, MA
9.9 142 reviews
Lenox, MA
09/22 – 09/25
$705/nighttotal: $2115 (3 )

Stylish Mid-century Modern Berkshires Cape

4 2
apartment , Lee
This 4-bedroom vacation home on a lake in Lee offers scenic views and is within walking distance of Greenock Country Club, Lee Library, and Animagic Museum of Animation. It has excellent user, location, and cleanliness ratings.
The house has a fully equipped kitchen, three bathrooms, a washing machine, a balcony, a smart TV, and free WiFi. It is pet-friendly, family-friendly, and has air conditioning, a terrace, a garden, and parking. It accommodates up to 8 guests and has a check-out time of 11:00 AM.
Enjoy Comfortable Elegance In This Secluded Grand Home Located In Town - Lenox, MA
10 87 reviews
Lenox, MA
07/13 – 07/16
$893/nighttotal: $2679 (3 )

Enjoy Comfortable Elegance In This Secluded Grand Home Located In Town

5 2
apartment , Lenox
This five-bedroom home is located in Lenox, a short walk from the town center and two miles from Tanglewood, offering a peaceful retreat in a prime location. The apartment has received excellent ratings for user experience, location, and cleanliness.
This 2600 square foot home comfortably accommodates nine guests. Amenities include a fully equipped kitchen, a Jacuzzi, a garden, and parking, along with access to a spa and internet.
Elmer Estate - Lenox, MA
10 5 reviews
Lenox, MA
09/22 – 09/25
$223/nighttotal: $669 (3 )

Elmer Estate

3 2
apartment , Pittsfield
This 3-bedroom, 1-bathroom apartment is situated on the Pittsfield/Lenox border, offering a 5-10 minute drive to Pittsfield's shopping, dining, and art venues, as well as nearby ski resorts.
This rental sleeps up to 5 guests and features internet, air conditioning, a kitchen, parking, and two porches with scenic views of the Berkshire Hills.
Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys! - Lenox, MA
9.6 15 reviews
Lenox, MA
09/22 – 09/25
$287/nighttotal: $861 (3 )

Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!

2 2
farm , Lenox
This Lenox, Massachusetts farmhouse rental is located on a mountainside, within 2 miles of the Housatonic River, Arrowhead, and the Arrowhead Museum.
This 2-bedroom, 1-bathroom vacation home sleeps 6, features a garden, air conditioning, Wi-Fi, and a kitchen with a refrigerator and microwave; nearby attractions include Guido's Marketplace and the Pleasant Valley Wilderness Sanctuary.

Best Lenox, MA vacation rentals with a balcony

Stunning Post & Beam Home Minutes From Lenox, Stockbridge And Tanglewood! - Lenox, MA
10 98 reviews
Lenox, MA
09/22 – 09/25
$1160/nighttotal: $3480 (3 )

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

5 2
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.
Light Filled Modern Rustic 3-bedroom House In Charming Stockbridge - Lenox, MA
Lenox, MA
09/22 – 09/25
$531/nighttotal: $1593 (3 )

Light Filled Modern Rustic 3-bedroom House In Charming Stockbridge

3 2
apartment , Stockbridge
This 3-bedroom, 3-bathroom Stockbridge rental offers a secluded experience down a private road, just a short drive from Tanglewood Music Center and the Norman Rockwell Museum.
This pet-friendly residence accommodates up to six guests with generous sleeping arrangements, features a deck overlooking acres of yard space, and provides air conditioning, internet, and parking.
Classic Stockbridge Cottage - Lenox, MA
10 17 reviews
Lenox, MA
09/22 – 09/25
$644/nighttotal: $1932 (3 )

Classic Stockbridge Cottage

4 2
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.
Modern And Spacious Berkshires Retreat 5 Bdrm 3 Bath - Lenox, MA
10 177 reviews
Lenox, MA
09/22 – 09/25
$671/nighttotal: $2013 (3 )

Modern And Spacious Berkshires Retreat 5 Bdrm 3 Bath

5 2
apartment , Lee
This renovated house is located on a quiet private street, just a 5-minute drive from both Lee and Lenox, offering easy access to charming towns and local attractions. The property enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This spacious 5-bedroom, 3-bathroom home comfortably sleeps up to 11 guests, with a total floor area of 2800 square feet. Enjoy features like a fully equipped kitchen, a family room with a pool table, a private terrace, and a garden, perfect for relaxing and entertaining.

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Best Lenox, MA vacation rentals with a sauna

Peaceful 1br Condo With Pond View - Lenox, MA
9.4 10 reviews
Lenox, MA
07/13 – 07/16
$428/nighttotal: $1284 (3 )

Peaceful 1br Condo With Pond View

1 2
apartment , Lee
This apartment is located in The Ponds at Foxhollow Resort in Lee, Massachusetts, a scenic area in the Berkshire Mountains close to a picturesque pond. The apartment, a spacious condo, can accommodate up to four guests with a master bedroom, a king-sized bed, and a double sleeper sofa.
The apartment comes with a fully equipped kitchen, a dining area, a Jacuzzi, a fireplace, and access to a range of resort amenities including indoor and outdoor pools, hot tubs, saunas, a fitness center, and outdoor activities like hiking, biking, and tennis.
Condo ∙ 2 Bedrooms ∙ 6 Guests - Lenox, MA
Lenox, MA
07/13 – 07/16
$501/nighttotal: $1503 (3 )

Condo ∙ 2 Bedrooms ∙ 6 Guests

2 2
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.
Hearth House | Prime Location! - Lenox, MA
Lenox, MA
07/13 – 07/16
$590/nighttotal: $1770 (3 )

Hearth House | Prime Location!

2 2
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.
Peaceful 1br Condo With Pond View - Lenox, MA
8.0 2 reviews
Lenox, MA
07/13 – 07/16
$469/nighttotal: $1407 (3 )

Peaceful 1br Condo With Pond View

1 2
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 fireplace

Lenox Grand Colonial With Pool By Evergreen Home - Lenox, MA
10 3 reviews
Lenox, MA
09/22 – 09/25
$762/nighttotal: $2286 (3 )

Lenox Grand Colonial With Pool By Evergreen Home

4 2
apartment , Lenox
This Lenox vacation home is situated in a rural setting, two miles from the Housatonic River, Arrowhead Museum, and Herman Melville's Arrowhead.
This 3,020-square-foot house features four bedrooms, three bathrooms, sleeps eight guests, and includes a private pool, fully equipped kitchen, and free Wi-Fi.
Berkshires Sanctuary With Outdoor Living Area & Firepit. 8minutes To Tanglewood! - Lenox, MA
10 15 reviews
Lenox, MA
09/22 – 09/25
$981/nighttotal: $2943 (3 )

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

5 2
apartment , Richmond
This 5-bedroom vacation rental is conveniently located near Richmond, just an 8-minute drive from Tanglewood Music Center and a 10-minute drive from the Hancock Shaker Village. The surrounding area offers a mix of cultural attractions, outdoor activities, and scenic beauty.
The spacious home comfortably accommodates up to 10 guests with 3 bathrooms, making it ideal for families or groups. Enjoy modern amenities like Wi-Fi, air conditioning, a jetted tub, a bidet, laundry facilities, a fully equipped kitchen, and access to a private garden, hot tub, and outdoor furniture.
Dancing Horse Lodge - Lenox, MA
9.7 360 reviews
Lenox, MA
09/22 – 09/25
$289/nighttotal: $867 (3 )

Dancing Horse Lodge

3 2
apartment , Pittsfield
This vacation rental is located in the mountains, just a short drive from Pittsfield's cultural attractions like the Colonial Theater, Berkshire Museum, and Housatonic River. The house has earned excellent ratings for its cleanliness, location, and overall experience.
The home has 3 bedrooms and 1 bathroom, comfortably accommodating up to 6 guests. Enjoy amenities like a fully equipped kitchen, a garden, and a relaxing mountain setting.
Classic Stockbridge Cottage - Lenox, MA
Lenox, MA
09/22 – 09/25
$639/nighttotal: $1917 (3 )

Classic Stockbridge Cottage

4 2
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.
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