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Best Vacation rentals and Airbnb offers in Lenox, MA
9.9 73 reviews
Lenox, MA
09/22 – 09/25
$143/nighttotal: $429 (3 )
Cute, Cozy And Comfortable Apartment
1 2
apartment , Lenox
This Lenoxdale apartment rental is conveniently located in the Berkshires, minutes from Lenox's downtown area and a short drive from Tanglewood, Kripalu Center for Yoga & Health, and Laurel Lake. The one-bedroom, one-bathroom unit sleeps two guests and features a kitchen with a fridge and microwave, air conditioning, parking, and a garden; nearby attractions include Kennedy Park and Olivia's Overlook for hiking enthusiasts.
This Richmond Shores cottage, a two-minute walk from Richmond Pond beach and close to Berkshire attractions, offers a private backyard overlooking Richmond Pond. The three-bedroom, one-bathroom house sleeps five, features a fully equipped kitchen with gas grill, washer/dryer, and provides access to two kayaks, a fire pit, and parking for three cars.
10 16 reviews
Lenox, MA
07/13 – 07/16
$426/nighttotal: $1278 (3 )
Exceptional Stockbridge Retreat
3 2
apartment , Stockbridge
This Stockbridge apartment rental is conveniently located near the Norman Rockwell Museum and Taglewood, offering easy access to Stockbridge Bowl and the town's attractions. The three-bedroom, one-bathroom unit sleeps eight guests and includes a fully equipped kitchen with dishwasher, air conditioning, a garden, parking, and internet access; enjoy nearby swimming, boating, and cultural experiences.
9.7 65 reviews
Lenox, MA
09/22 – 09/25
$274/nighttotal: $822 (3 )
Spacious Family-ready Home Fully Fenced Yard - Lee
1 2
apartment , Lee
This apartment is conveniently located in Lee, within easy walking distance of the town's charming center and its many attractions. The apartment has received excellent ratings for location, cleanliness, and user experience. The apartment features three bedrooms and two bathrooms, comfortably accommodating up to eight guests. Enjoy a modern kitchen with a full range of appliances, a private backyard, and a 4K TV for entertainment.
Lenox, MA
07/13 – 07/16
$1079/nighttotal: $3237 (3 )
Belden Farm - Walk To Tanglewood !
1 2
apartment , Lenox
This historic estate in Lenox offers an exclusive country escape on 15 acres, featuring open fields and sugar maples, with walkable access to Tanglewood and a 3-minute drive to Stockbridge Bowl and downtown Lenox. This 10-guest capacity residence includes a chef's kitchen with a Viking stove, a music parlor with a Steinway grand piano, a yoga and meditation room, and private access to the home and grounds, perfect for a family-friendly stay with pets allowed and internet.
10 7 reviews
Lenox, MA
09/22 – 09/25
$447/nighttotal: $1341 (3 )
Historic Haven At 93 Church St.
1 2
apartment , Lenox
This Lenox, Massachusetts apartment rental is centrally located on Church Street in downtown Lenox, offering easy walking access to shops, restaurants, and cultural attractions like the Norman Rockwell Museum and Tanglewood. This two-bedroom, one-and-a-half-bathroom unit sleeps four guests and features exposed wood beams, a full kitchen, air conditioning, parking, and internet access.
Lenox, MA
07/13 – 07/16
$334/nighttotal: $1002 (3 )
Extended Stay- Full Kitchen 1br Apartment In Downtown Pittsfield
1 2
apartment , Pittsfield
This Pittsfield apartment is located near Tanglewood Music Center, Colonial Theater, Herman Melville's Arrowhead, and Hancock Shaker Village. This one-bedroom, one-bathroom unit accommodates up to four guests and features a king bed, a sofa bed, air conditioning, and internet.
9.9 20 reviews
Lenox, MA
09/22 – 09/25
$196/nighttotal: $588 (3 )
Eliza Suite
1 2
apartment , Lee
This Lee, Massachusetts apartment is conveniently located within walking distance of Lee's shops and cafes, offering easy access to local attractions. The one-bedroom unit features a full kitchen, air conditioning, parking, and accommodates up to three guests, perfect for a couple or solo traveler exploring the Berkshires.
9.8 172 reviews
Lenox, MA
09/22 – 09/25
$518/nighttotal: $1554 (3 )
Restored 1881 Farm House
1 2
house , Lenox
This restored 1881 farmhouse is located in Lenox, just over 3 miles from both Tanglewood and Cranwell Spa & Golf Club, offering a convenient base for exploring the Berkshires. The property has received excellent ratings for its cleanliness, location, and overall experience, making it a popular choice for travelers. This charming house spans 1290 square feet and comfortably accommodates up to 4 guests in its two bedrooms. The property features a fully equipped kitchen, a terrace and balcony, a garden, free Wi-Fi, and a convenient location near skiing and cycling trails, the Norman Rockwell Museum, and other Lenox attractions.
8.4 316 reviews
Lenox, MA
07/13 – 07/16
$321/nighttotal: $963 (3 )
The Ponds At Foxhollow
1 2
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.
9.8 47 reviews
Lenox, MA
09/22 – 09/25
$436/nighttotal: $1308 (3 )
Spacious 3 Bedroom Apt In Lenox Historic Downtown
1 2
apartment , Lenox
This Lenox apartment rental is centrally located in downtown Lenox, Massachusetts, a 15-minute walk from Tanglewood and within walking distance of numerous restaurants and shops. The three-bedroom, two-bathroom unit sleeps six guests and features a fully equipped kitchen with a refrigerator, freezer, microwave, and dishwasher, plus free on-site parking, air conditioning, and a garden.
9.9 88 reviews
Lenox, MA
09/22 – 09/25
$323/nighttotal: $969 (3 )
Lenox Ma.
1 2
apartment , Lenox
This charming one-bedroom apartment in Downtown Lenox is a perfect choice for travelers seeking convenience, comfort, and a touch of local charm. Located just a short walk from Tanglewood and other cultural attractions, it offers a cozy retreat with a well-equipped kitchen, air conditioning, and private parking. With excellent user, location, and cleanliness ratings, this apartment ensures a comfortable and enjoyable stay. It accommodates up to 2 guests and features a private bathroom, providing ample space and privacy for couples or small groups. Whether you're looking to explore Lenox's vibrant culinary scene or attend a concert at Tanglewood, this apartment offers the perfect home base.
Search Family Vacation Rentals in Lenox, MA
Lenox, MA family-friendly vacation rentals provide a perfect base for outdoor adventure.
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.
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.
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.
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
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.
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.
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.
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.
Frequently Asked Questions about vacation rentals in Lenox, MA
What are some interesting places to visit in or near Lenox, MA?
Lenox is home to the Tanglewood Music Center, a renowned summer music festival. You can also visit the Edith Wharton's The Mount, her former estate, or the Norman Rockwell Museum in nearby Stockbridge.
What are the best Airbnb and vacation rentals in Lenox, MA?
Which walking or cycling routes are the best in Lenox, MA?
The scenic Housatonic River Rail Trail is a great option for walking or cycling. It's a paved, mostly flat trail that runs along the Housatonic River, offering beautiful views. You can also explore the Lenox town center and its charming streets.
What sports or outdoor activites can visitors enjoy in and around Lenox, MA?
Hiking, biking, and fishing are popular activities in the area. You can explore the trails of the Berkshires, go fishing on the Housatonic River, or visit the nearby Jiminy Peak Mountain Resort for skiing in the winter.
What are the best vacation rentals with a pool in Lenox, MA?
What other towns or cities can be easily accessed from Lenox, MA?
You can easily reach nearby towns like Stockbridge, Great Barrington, and Pittsfield. If you want to venture a bit further, you can visit Springfield, MA, or Albany, NY, both about a 1.5-hour drive away.
What are the best rentals for families and kids in Lenox, MA?
What amenities are commonly available in vacation rentals in Lenox, MA?
Vacation rentals in Lenox often come equipped with kitchens, laundry facilities, and comfortable living spaces. Many also have outdoor amenities like decks or patios, perfect for enjoying the fresh air. You can find rentals with different sizes and features to suit your needs.
What are the best rentals or Airbnbs with a jacuzzi in Lenox, MA?
What time of year is best to rent a vacation rental Lenox, MA?
The best time to visit Lenox depends on your preferences. Summer is popular for the Tanglewood Music Festival and outdoor activities. Fall offers stunning foliage, and winter is ideal for skiing at Jiminy Peak. Spring is a beautiful time to enjoy the blooming flowers.
Destinations nearby
Best Lenox, MA vacation rentals with a sauna
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.
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.
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.
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
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.
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.
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.
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.