Best apartment offers in Lenox, MA

119 available apartment offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Lenox, MA apartments
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

119 Holiday apartments Lenox, MA

Best family friendly Lenox, MA Holiday Apartments and Self Catering Accommodations

Among the 119 accommodations in Lenox, MA, here are the 4 best family friendly holiday apartments

Grand Berkshire Manor By Evergreen Home - Lenox, MA
10 75 reviews
Lenox, MA
13/07 – 16/07
SG$1505/nighttotal: SG$4515 (3 )

Grand Berkshire Manor By Evergreen Home

1 2
apartment , Pittsfield
This five-bedroom house is located in the Berkshires, just a short drive from Pittsfield and within easy reach of attractions like Tanglewood, Mass MoCA, and the Norman Rockwell Museum. It has received excellent ratings for location, cleanliness, and overall user experience.
This spacious property comfortably accommodates up to 10 guests and features a fully equipped kitchen, laundry facilities, a private swimming pool, and a garden. Guests can enjoy relaxing evenings on the expansive grounds with a barbecue, as well as explore the charming old house character and its unique features.
Light Filled - Modern Rustic Home - Lenox, MA
Lenox, MA
13/07 – 16/07
SG$653/nighttotal: SG$1959 (3 )

Light Filled - Modern Rustic Home

4 2
apartment , Stockbridge
This secluded apartment, located on a quiet dead-end road in Stockbridge, offers a peaceful retreat with easy access to woodland and a stream, ideal for those seeking a tranquil getaway.
This pet-friendly flat accommodates up to six guests and features a well-equipped kitchen, air conditioning, two bathrooms, and an outdoor deck, with ample garden space for recreation and exploration.
Centrally Located In The Berkshires - Cozy Bungalow In Se Pittsfield! - Lenox, MA
10 5 reviews
Lenox, MA
22/09 – 25/09
SG$325/nighttotal: SG$975 (3 )

Centrally Located In The Berkshires - Cozy Bungalow In Se Pittsfield!

2 2
apartment , Pittsfield
This charming bungalow is situated in the city centre of Pittsfield, just 5km from Bousquet Ski Resort, 20km from Jiminy Peak and 15km from Tanglewood in Lenox, offering easy access to the area's attractions. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The home sleeps up to 5 guests and spans 93 square metres. It features a fully equipped kitchen, a spa, air conditioning and a private deck with a grill, perfect for enjoying the outdoors.
Lovely Berkshire Apartment. Private & Peaceful - Lenox, MA
10 145 reviews
Lenox, MA
22/09 – 25/09
SG$366/nighttotal: SG$1098 (3 )

Lovely Berkshire Apartment. Private & Peaceful

1 2
apartment , Lee
This one-bedroom flat is located in a desirable area of Lee, just 8 kilometres from Tanglewood and 10 kilometres from Jacobs Pillow, making it a great base for exploring the Berkshires. The apartment has received excellent ratings for its cleanliness, location, and overall user experience.
The flat has a spacious living area and can comfortably accommodate up to four guests. It features a fully equipped kitchen, a cosy fireplace, a private patio with a gazebo, and stunning mountain views.

Best Lenox, MA holiday apartments with air conditioning

Berkshires Chalet Mins To Tanglewood/lenox - Lenox, MA
Lenox, MA
13/07 – 16/07
SG$929/nighttotal: SG$2787 (3 )

Berkshires Chalet Mins To Tanglewood/lenox

4 2
apartment , Richmond
This spacious four-bedroom, three-bathroom flat is located in Richmond, approximately 6.4 kilometres from Tanglewood and close to numerous Berkshire attractions, offering convenient access to outdoor pursuits and summer theatre venues.
This modern, open-concept two-storey residence accommodates up to ten guests and features a new kitchen with soapstone counters and stainless steel appliances, air conditioning, a Jacuzzi, a screened porch, and secluded grounds with a covered outdoor hot tub.
Whistler's Inn/the Garden Room (#9) - Lenox, MA
9.8 16 reviews
Lenox, MA
13/07 – 16/07
SG$451/nighttotal: SG$1353 (3 )

Whistler's Inn/the Garden Room (#9)

1 2
apartment , Lenox
Whistler's Inn/the Garden Room (#9) in Lenox, Massachusetts, is a historic English Tudor mansion dating from 1870, situated near Tanglewood and other Berkshire cultural attractions.
This one-bedroom, one-bathroom guesthouse offers accommodation for up to three guests and features a grand piano, a 2,000-volume library with complimentary sherry and tea, a gourmet breakfast buffet, and access to beautiful gardens.
Dancing Horse Lodge - Lenox, MA
9.7 360 reviews
Lenox, MA
22/09 – 25/09
SG$371/nighttotal: SG$1113 (3 )

Dancing Horse Lodge

3 2
apartment , Pittsfield
This house is located in the Berkshire Mountains, just 3 kilometres from Pittsfield's downtown area, close to the Housatonic River, Colonial Theater, and Berkshire Museum. This property has received excellent ratings for location, cleanliness, and user experience.
This 3-bedroom, 1-bathroom house can accommodate up to 6 guests. The house is equipped with modern amenities such as a washing machine, a Smart TV, and a coffee/tea maker, plus a garden and barbecue grills for outdoor relaxation and dining.
Imagine Being Lakeside, Kayaks/fishing/ev Charger - Lenox, MA
9.6 20 reviews
Lenox, MA
22/09 – 25/09
SG$769/nighttotal: SG$2307 (3 )

Imagine Being Lakeside, Kayaks/fishing/ev Charger

4 2
apartment , Lenox
This Lenox holiday home, near the beach and a 2.4km walk from Wyndhurst Golf & Club and The Mount, offers easy access to local attractions including Shakespeare and Company and Ventfort Hall Mansion within 5km.
The 176 square metre property boasts four bedrooms, two bathrooms, sleeping up to ten guests, and features a fully equipped kitchen, private balcony, garden, parking, and internet access.

Frequently asked questions about apartment rentals in Lenox, MA

Destinations nearby

Best Lenox, MA holiday apartments with parking

Historic Haven At 93 Church St. - Lenox, MA
10 7 reviews
Lenox, MA
22/09 – 25/09
SG$575/nighttotal: SG$1725 (3 )

Historic Haven At 93 Church St.

1 2
apartment , Lenox
This two-bedroom Lenox apartment on Church Street offers a central downtown location, within walking distance of Lenox's cultural attractions.
The 2-bedroom, 1.5-bathroom flat sleeps four guests and includes amenities such as Wi-Fi, parking, and air conditioning; further details on specific amenities are available upon request.
Urban Peak Escape - Lenox, MA
10 1 review
Lenox, MA
22/09 – 25/09
SG$626/nighttotal: SG$1878 (3 )

Urban Peak Escape

2 2
apartment , Lenox
This two-bedroom apartment in Lenox is located just 2.3 kilometres from the Tanglewood Music Centre, a world-renowned concert venue.
The apartment offers a spacious 1,115 square metre living space with a private balcony, a fully equipped kitchen and a washing machine, making it ideal for families or groups of up to seven people.
Hidden Oasis In The Mountains By Evergreen Home - Lenox, MA
9.9 159 reviews
Lenox, MA
22/09 – 25/09
SG$1080/nighttotal: SG$3240 (3 )

Hidden Oasis In The Mountains By Evergreen Home

5 2
apartment , Pittsfield
This Berkshire County colonial-style house, situated atop a hill overlooking October Mountain, is 11km from Pittsfield and 11km from Lenox, offering easy access to Bousquet Mountain Ski Area.
This 334 square metre property sleeps ten guests in five bedrooms and three bathrooms, boasting a well-equipped kitchen, jacuzzi, fitness centre, and extensive outdoor space including a hot tub, fire pit, and stone patio; additional amenities include a games room with pool table and ping pong table.
1500 Sqft Private Entrance With Beautiful Views Of The Berkshire Mountains - Lenox, MA
10 47 reviews
Lenox, MA
22/09 – 25/09
SG$525/nighttotal: SG$1575 (3 )

1500 Sqft Private Entrance With Beautiful Views Of The Berkshire Mountains

2 2
apartment , Lee
This apartment is situated in Lee, Western Massachusetts, just 8 kilometres from Tanglewood, 4 kilometres from Stockbridge Theatre and 13 kilometres from Jacob’s Pillow, offering easy access to popular attractions. The property boasts excellent user ratings, making it a popular choice for travellers.
The apartment is a spacious 139 square metre property with two bedrooms and one bathroom, comfortably accommodating up to five guests. You'll enjoy a fully equipped kitchen, a jacuzzi, a terrace, a garden, a spa, parking and access to a range of amenities including air conditioning, internet, a washing machine and a dryer.

Best Lenox, MA apartment rentals with a garden

Belden Farm - Walk To Tanglewood ! - Lenox, MA
Lenox, MA
13/07 – 16/07
SG$1387/nighttotal: SG$4161 (3 )

Belden Farm - Walk To Tanglewood !

1 2
apartment , Lenox
This historic country home, a National Historic Landmark built in 1881, is located on a 15-hectare hilltop in Lenox, offering a peaceful rural escape within walking distance to Tanglewood and a 3-minute drive to downtown Lenox and Stockbridge Bowl.
This 6-bedroom property accommodates up to 10 guests and features a chef's kitchen with a Viking stove, a music parlour with a vintage Steinway grand piano, a dedicated yoga and meditation room, a home office, air conditioning, a garden, a fitness centre, and a veranda.
Hearth House | Prime Location! - Lenox, MA
Lenox, MA
13/07 – 16/07
SG$758/nighttotal: SG$2274 (3 )

Hearth House | Prime Location!

2 2
apartment , Stockbridge
This Stockbridge flat is located moments from the Norman Rockwell Museum and Tanglewood, offering easy access to local points of interest and natural landscapes, with the Berkshire Botanical Garden a mere 200 meters away.
This spacious 218 square meter residence features 3 bedrooms and 2.5 bathrooms, accommodating up to 6 guests with amenities including Wi-Fi, air conditioning, a garden, sauna, and parking.
Berkshire Hills Country 
Retreat - Lenox, MA
9.9 23 reviews
Lenox, MA
22/09 – 25/09
SG$308/nighttotal: SG$924 (3 )

Berkshire Hills Country Retreat

1 2
apartment , Lee
This Berkshire Hills house rental near October Mountain is conveniently located within a 5-minute drive (approximately 8km) of Lee, Lenox, and Stockbridge, offering easy access to the region's attractions.
This two-bedroom, one-bathroom property sleeps four guests and boasts a fully equipped kitchen with a fridge, freezer, and microwave, a 55-inch Roku TV, air conditioning, and a garden; parking is also available.
Spacious Lenox Farmhouse | Retreat Near Tanglewood - Lenox, MA
10 16 reviews
Lenox, MA
13/07 – 16/07
SG$807/nighttotal: SG$2421 (3 )

Spacious Lenox Farmhouse | Retreat Near Tanglewood

1 2
apartment , Lenox
This Berkshires farmhouse, near Lenox, Massachusetts, is situated 14.5km from Tanglewood and a short drive from Stockbridge.
The 2000+ sq ft property boasts three bedrooms, two bathrooms, sleeping seven guests, and features a large open-plan living area, a fully equipped kitchen including a dishwasher, and outdoor amenities such as a BBQ and fire pit.
©2026 cozycozy.com