Holiday Rentals in Lenox, MA

232 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Lenox, MA holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

232 Holiday rentals and Airbnb in Lenox, MA

Best family friendly Lenox, MA holiday rentals

Among the 232 accommodations in Lenox, MA, here are the 4 best family friendly rentals

Cheerful 3 Bedroom House Abutting State Forest - Lenox, MA
10 2 reviews

Cheerful 3 Bedroom House Abutting State Forest

house, Lenox
This three-bedroom split ranch in Lenox is located directly beside October Mountain State Forest, offering immediate access to nature and a short drive to Lenox town centre and its cultural attractions including Tanglewood and the Norman Rockwell Museum.
This family-friendly property sleeps six guests and features a kitchen with a fridge, microwave, and dishwasher, air conditioning, and internet access, with nearby opportunities for hiking, biking, kayaking, and fishing.
Serene And Refined Berkshires Retreat, Close To Kripalu, Gardens & 3 Ski Resorts - Lenox, MA
10 6 reviews

Serene And Refined Berkshires Retreat, Close To Kripalu, Gardens & 3 Ski Resorts

apartment, Stockbridge
This five-bedroom Stockbridge house, ideal for families or groups of up to eight, is situated a 2.4km walk from the Berkshire Botanical Garden and Housatonic River, and within 3.2km of the Norman Rockwell Museum and Naumkeag.
The smoke-free property boasts a fully equipped kitchen, private patio, fireplace, and free Wi-Fi; a spa and parking are also available.
Berkshire Vacation Home In Lee - Lenox, MA
9.9 105 reviews

Berkshire Vacation Home In Lee

apartment, Lee
This spacious five-bedroom holiday home is conveniently located in Lee, close to the city centre and a lake, offering easy access to local attractions, shops and restaurants. The property has received excellent ratings for its cleanliness, location and overall user experience.
The apartment is perfect for large families or groups, with multiple living areas, a fully equipped kitchen and a Florida room leading to a deck overlooking the pool. Guests can enjoy a range of on-site amenities, including a swimming pool, fitness centre and garden, as well as explore the nearby ski resorts, cultural sites and attractions.
Cozy 4br Colonial, Walk To Downtown Lee - Lenox, MA
9.7 58 reviews

Cozy 4br Colonial, Walk To Downtown Lee

apartment, Lee
This four-bedroom house is located in Lee, just a short walk from the town centre and a five-minute drive from Lake Laurel, offering easy access to shops, restaurants, and outdoor activities. The property has been rated excellent for location, cleanliness, and user experience.
The spacious house can accommodate up to eight guests and features a large dining table, a playground, and a 55-inch TV. The house also has a private backyard with a deck, a hammock, a fire pit, a barbecue, and outdoor furniture, perfect for relaxing and entertaining.

Best Lenox, MA holiday rentals with a balcony

Extended Stay- Full Kitchen 1br Apartment In Downtown Pittsfield - Lenox, MA
10 1 review

Extended Stay- Full Kitchen 1br Apartment In Downtown Pittsfield

apartment, Pittsfield
This one-bedroom flat in Pittsfield is conveniently located for exploring local culture and history, with Tanglewood Music Center and Colonial Theater just a short distance away, and Herman Melville's Arrowhead and Hancock Shaker Village also nearby.
This apartment offers accommodation for up to four guests, featuring a king-size bed, a sofa bed in the living room, air conditioning, and complimentary Wi-Fi, and is within easy reach of the Berkshire Museum and Bousquet Ski Area.
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
Village View, a ten-room Victorian house in downtown Lenox, Massachusetts, is a three-block walk (approximately 0.24 km) from the bus stop and within easy reach of restaurants, shops, and historic sites such as Ventfort Hall and The Mount.
This five-bedroom, three-bathroom property offers guests a fully equipped kitchen, a jetted tub, parking for up to three cars, and a secluded backyard with a gas grill; it comfortably accommodates larger groups and is ideal for exploring Lenox's attractions, including Kennedy Park and Pleasant Valley Bird Sanctuary.
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 from Tanglewood.
This expansive property comprises two homes, accommodating up to 18 guests with eight bedrooms and five bathrooms, featuring a chef's kitchen, separate guest house, and ample parking for eight vehicles.
Centrally Located Historical Home - Lenox, MA
10 6 reviews

Centrally Located Historical Home

apartment, Lee
This private country escape in Lee offers unobstructed rolling hillsides and mountain views, situated just 10 kilometres from Tanglewood, Shakespeare and Co, Jacob's Pillow, Barrington Stage, and The Mount.
This 120 square metre flat accommodates up to four guests in two bedrooms, each with an en-suite bathroom, and features a fully equipped kitchen, central heating, air conditioning, a terrace, garden, and parking.

Frequently asked questions about holiday rentals in Lenox, MA

Popular destinations

Best Lenox, MA holiday rentals with a sauna

Peaceful 1br Condo With Pond View - Lenox, MA
8.0 2 reviews

Peaceful 1br Condo With Pond View

apartment, Lenox
This Lenox apartment, a peaceful one-bedroom condo near the Pleasant Valley Wildlife Sanctuary, offers easy access (distances unspecified but likely within a few kilometres) to cultural attractions such as The Mount and the Frelinghuysen Morris House and Studio.
Sleeping four guests, the property boasts two bathrooms and is likely fully equipped, providing a tranquil base for exploring Lenox's natural and cultural offerings, including the Berkshire Scenic Railway Museum and The Bookstore.
Hearth House | Prime Location! - Lenox, MA
10 1 review

Hearth House | Prime Location!

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.
Berkshires Mid-century Retreat! - Lenox, MA
No reviews

Berkshires Mid-century Retreat!

apartment, West Stockbridge
This West Stockbridge holiday home is situated a 7-minute drive from Tanglewood Music Centre and a 6-minute drive from Hotchkiss Mobile Studio.
This five-bedroom, three-bathroom property offers a swimming pool, garden, terrace, hot tub, and Wi-Fi, making it ideal for families exploring local attractions and natural beauty spots.
Peaceful 1br Condo With Pond View - Lenox, MA
9.5 13 reviews

Peaceful 1br Condo With Pond View

apartment, Lee
This apartment is located in The Ponds at Foxhollow Resort in Lee, Massachusetts, just a short distance from the picturesque Berkshire Mountains. The resort is situated near a tranquil pond, offering scenic views and a peaceful atmosphere.
This comfortable apartment, suitable for up to four guests, features a master bedroom with a king-size bed, a master bathroom with a jacuzzi, a fully equipped kitchen, a dining area, and a living area with a double sleeper sofa. The apartment benefits from a range of amenities including a swimming pool, jacuzzi, sauna, fitness centre, and free Wi-Fi, alongside a variety of activities such as tennis courts, a putting green, and access to bicycles for exploring the surrounding area.

Best Lenox, MA holiday rentals with a fireplace

Imagine Being Lakeside, Kayaks/fishing/ev Charger - Lenox, MA
9.6 23 reviews

Imagine Being Lakeside, Kayaks/fishing/ev Charger

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.
Berkshire Mountain Retreat - Lenox, MA
9.9 52 reviews

Berkshire Mountain Retreat

studio, Richmond
This Richmond, Massachusetts studio apartment is situated near the Berkshire High Road Trailhead, less than 0.4 kilometres from miles of hiking and biking trails, and within a short drive of attractions such as Tanglewood and Kripalu.
The self-contained apartment, sleeping up to two guests, boasts a private patio, parking for two cars, a fully equipped kitchenette (fridge, freezer, microwave), air conditioning, and access to a swimming pool and garden; nearby Bartlett's Apple Orchard offers fresh produce.
Spacious Lenox Home Near Tanglewood - Lenox, MA
10 1 review

Spacious Lenox Home Near Tanglewood

apartment, Lenox
This four-bedroom, three-bathroom flat in Lenox, situated in the Berkshires, offers picturesque views of a wildflower meadow and mountains, located a short drive from downtown Lenox and Tanglewood.
Accommodating up to 12 guests, this residence features a well-equipped kitchen, a 28-square-meter screened porch, and a peaceful garden, with amenities including internet, air conditioning, and parking.
Modern Chalet Near Tanglewood & Downtown Lenox - Lenox, MA
9.8 45 reviews

Modern Chalet Near Tanglewood & Downtown Lenox

chalet, Lenox
This modern A-frame cabin is located in Lenox, just a short walk from Tanglewood, Kennedy Park, and Kripalu, offering easy access to cultural events, outdoor recreation, and wellness activities. The property has consistently received excellent ratings for location, cleanliness, and overall guest experience.
The cabin features a split-level mezzanine design, offering a blend of modern and rustic charm, and can accommodate up to six guests. Enjoy stunning views of the Berkshires from the open living room with triple-height ceilings, relax on the sun porch or deck, or unwind in the garden hammocks. The cabin also includes a fully equipped kitchen, a private garden, a ping pong table, and BBQ facilities available upon request.
©2026 cozycozy.com