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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

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

Friendly Hills | Passive Home Ev Charger

apartment, Hancock
This mid-century modern vacation rental in Pittsfield, near Hancock Shaker Village, offers easy access to Pittsfield attractions like Bousquet Ski Area and the Berkshire Museum.
The three-bedroom, two-bathroom home features a fully equipped kitchen with a fridge, microwave, and dishwasher; high-speed Wi-Fi; air conditioning; and parking, all within a unique design inspired by Frank Lloyd Wright on six private acres with hiking trails and ponds.
Spacious Historic Home In The Berkshires! - Lenox, MA
9.8 21 reviews

Spacious Historic Home In The Berkshires!

apartment, Pittsfield
This Pittsfield vacation home offers convenient access to the Colonial Theatre, Berkshire Athenaeum, and Berkshire Museum, all within a 10-minute walk, and is less than a mile from the Housatonic River and Barrington Stage Company.
This 3,300-square-foot house features seven bedrooms, two bathrooms, accommodates nine guests, and includes a fully equipped kitchen, fireplace, in-house washer, private garden, balcony, and parking.
6 Mi To Tanglewood! High-end Lee Apartment - Lenox, MA
No reviews

6 Mi To Tanglewood! High-end Lee Apartment

apartment, Lee
This historic 1738 property in Lee, with a modern 2010 addition, offers a private forest-view balcony and is located just under a mile from downtown, 2 miles from Lee Premium Outlets, and 4 miles from Stockbridge and the Norman Rockwell Museum.
This 1500 square foot, family-friendly apartment comfortably accommodates up to 4 guests with 2 bedrooms, 1 bathroom, central air conditioning, high-speed WiFi, an upgraded kitchen with a dishwasher, and an in-unit washer/dryer.
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.

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.
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.
Serene Lenox Hills Cottage - Berkshires - Lenox, MA
9.6 45 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.
Comfortable Elegance On Secluded Property In Lenox - Lenox, MA
10 97 reviews

Comfortable Elegance On Secluded Property In Lenox

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.

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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.
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.
Lakeside Estate: 2 Homes For Family Gatherings - Lenox, MA
10 1 review

Lakeside Estate: 2 Homes For Family Gatherings

apartment, Lenox
This exclusive lakeside estate in Lenox, Massachusetts, offers private lake access and is within walking distance of The Mount, Edith Wharton's Home, and a short drive to Tanglewood.
This spacious rental property features 8 bedrooms and 5 bathrooms, accommodating up to 18 guests with amenities including a chef's kitchen, internet, air conditioning, and year-round activities such as skiing at nearby Bousquet and Ski Butternut.
Fall Weekends And Ski Season Is Here! - Lenox, MA
No reviews

Fall Weekends And Ski Season Is Here!

apartment, Stockbridge
This 1800 sq ft, 3-bedroom, 2-bathroom West Stockbridge vacation home is centrally located, offering 2 miles to Tanglewood, less than 5 minutes to Stockbridge Town Beach, and approximately 15 minutes to Great Barrington and Ski Butternut, with easy access to Naumkeag Museum and Berkshire Botanical Garden. This pet-friendly rental accommodates up to 6 guests and features a fully equipped kitchen with an induction cooktop, a wood-burning fireplace, a sun deck with a fire pit and BBQ grill overlooking wetlands, and an office/bonus room, all with high-speed internet and multiple smart TVs.

Best Lenox, MA vacation rentals with a sauna

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

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
8.0 332 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.
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.
Hearth House | Prime Location! - Lenox, MA
10 2 reviews

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.

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.

Peaceful 1br Condo With Pond View - Lenox, MA
9.5 13 reviews

Peaceful 1br Condo With Pond View

apartment, Lee

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.

Built For A Us Secretary Of State 13k Sf In Lenox - Lenox, MA
10 71 reviews

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

house, Lenox
Home Away From Home: Minutes To Tanglewood. - Lenox, MA
9.9 58 reviews

Home Away From Home: Minutes To Tanglewood.

apartment, Lenox
Hidden Oasis In The Mountains By Evergreen Home - Lenox, MA
9.9 172 reviews

Hidden Oasis In The Mountains By Evergreen Home

apartment, Pittsfield
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.

Expansive Mountainside Escape By Evergreen Home - Lenox, MA
10 4 reviews

Expansive Mountainside Escape By Evergreen Home

apartment, West Stockbridge
Historic Stockbridge Villa On 25 Acres - Lenox, MA
10 20 reviews

Historic Stockbridge Villa On 25 Acres

house, 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
Beautiful 2bd Villa In Berkshires Resort - Lenox, MA
9.3 18 reviews

Beautiful 2bd Villa In Berkshires Resort

house, Lee

Discover Vacation Rentals with Jacuzzi in Lenox, MA

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

Berkshire Mountain Lodge - Lenox, MA
8.9 1792 reviews

Berkshire Mountain Lodge

house, Pittsfield
Luxury Fox Hollow Estate Home On Laurel Lake - Dream Location, Hot Tub, Kayaks++ - Lenox, MA
9.2 67 reviews

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

apartment, Lee
Richmond Ranch W/ Hot Tub By Evergreen Home - Lenox, MA
10 5 reviews

Richmond Ranch W/ Hot Tub By Evergreen Home

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

Berkshires Chalet Mins To Tanglewood/lenox

apartment, Richmond
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