
Family-friendly holiday rentals in Lenox
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Lenox

Total holiday rentals
Explore 130 holiday rentals in Lenox

Nightly prices starting at
Lenox holiday rentals start at $221 NZD per night before taxes and fees

Verified guest reviews
Over 4,720 verified reviews to help you choose

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
130 of Lenox holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Lenox rentals

4.9 Average rating
Lenox stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated family-friendly rentals in Lenox
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Mid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Berkshires Cottage by Lake. Year Round Adventures.
THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. $29. pet fee = approved Pet Agreement.

Berkshire 4 season home
The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

Berkshire Mountain retreat with Urban eco-luxuries
600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Berkshire Treehouse Retreat
Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.

Private 2nd-floor studio on a working produce farm
Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Bedroom Forest View I Sauna I Fire-pit I Trails
Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Lovely Downtown Lenox apt, walk to everything!
Experience the best of the Berkshires in a beautiful, spacious apartment right in the center Lenox. This updated space is filled with natural light and hardwood floors, great for families or friends looking to experience culture and countryside. Walking distance to Tanglewood, Shakespeare & Co, Kennedy Park, restaurants, and shopping. On second floor of a Historic building with a deck that has a birds eye view of town. 7 min to Bousquet Mountain.

Historical Downtown 1 Bedroom Apartment
Located in the heart of historical downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in kitchen has a table for two, stainless appliances, and an array of cooking essentials. The living room features a comfortable sectional and a flat screen TV for relaxing. Wi-Fi is available throughout the space. Central heat and air to provide a comfortable environment in any season. All linens and towels are provided.

HOT TUB! Dog & Family Friendly in the Berkshires!
Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

Summer Mountain Retreat + Views, Fire Pit, Hot Tub
Escape to your modern mountain retreat—perfect for Summer getaways! Just 15 mins to Tanglewood, MASS MoCA & The Clark, and close to scenic hikes, waterfalls, farm stands, breweries, and charming small towns. Soak in the wood-fired hot tub, enjoy evenings around the Breeo fire pit, cook fresh seasonal meals, and unwind in peaceful privacy. With EV charging and a quiet workspace, it’s ideal for refreshing escapes or Summer adventures.

GreenHouse
Relax and enjoy the Berkshires at this peaceful place to stay in the beautiful Berkshires of western Massachusetts. GreenHouse is the guest cottage for the historic Hyde House which is on the National Register of Historic Places. Located within walking distance of Lee, Ma, the house is also conveniently located near Stockbridge and Lenox.
Popular amenities for Lenox family-friendly rentals
Family-friendly home rentals with a hot tub

Artist Cottage

Amazing Berkshire Mountains Cabin

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

Boutique TINY home+private HOT TUB-walk to Main St

Jaw dropping mountain & lake views

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

Hilltown Cabin Hideaway: A River Runs Through It!

Livingston Farmhouse Escape with hot tub and sauna
Family- and pet-friendly home rentals

Stylish Mid-century Modern Berkshires Cape

Cozy lakehouse

Cozy Hilltown Cottage

Sweet Victorian in Housatonic

Design-Forward Riverfront Cabin on 120 Acres

Luxury Barn Retreat Near Hudson & the Berkshires

Newly Renovated Cabin in the Country

Wildlife Lakeside Cottage; views/wildlife
Family-friendly home rentals with a pool

Berkshire Vacation Home in Lee

Enjoy every season the Berkshires have to offer.

Cozy cottage with pool, walking distance to lake

Cozy Cottage with pool and walk to lake

Berkshire Getaway Ranch 3 acres + saltwater pool

Hudson River Sunset Getaway

Saltwater Pool & Cottage@ Hudsons ClearCreekFarm

Charming Lakefront Cabin with Hot Tub
When is the best time to visit Lenox?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $506 NZD | $523 NZD | $501 NZD | $499 NZD | $509 NZD | $585 NZD | $699 NZD | $626 NZD | $565 NZD | $550 NZD | $543 NZD | $538 NZD |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Destinations to explore
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- Family-friendly rentals Berkshire County
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- Family-friendly rentals United States
- Hunter Mountain
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Windham Mountain
- June Farms
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Taconic State Park
- Thacher State Park
- Kent Falls State Park
- Bash Bish Falls State Park
- Hunter Mountain Resort
- Mohawk Mountain Ski Area
- Bousquet Mountain Ski Area
- Millbrook Vineyards & Winery
- Rensselaer Polytechnic Institute
- Hudson Chatham Winery
- University of Massachusetts Amherst
- MVP Arena
- Naumkeag
- New York State Museum
- Poets' Walk Park
- Massachusetts Museum of Contemporary Art





