
Family-friendly vacation rentals in Lee
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Top-rated family-friendly rentals in Lee
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Restored 1735 Granary I King Bed + Views & Pool
Restored 1735 granary on a peaceful Berkshires farmhouse compound. With 15-ft vaulted ceilings, original wide-plank floors, and mountain views, this design-forward retreat blends rustic charm with modern ease. Features a king bedroom, eat-in kitchen, and bathroom with soaking tub + standing shower. Centrally located in the Berkshires and just minutes to Lenox and Tanglewood. A quiet, light-filled space perfect for couples, creatives, and anyone seeking rest, reflection, and connection to nature.

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.

Cozy Berkshires Cottage
Stay in a cozy, newly remodeled Berkshires 1920's cottage! We've added bedrooms and a bathroom with a soaking tub upstairs, expanded the first floor bathroom and added a laundry room. The cottage is set back from the main road, easily accessible yet private. -Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. -Ideal for couples, adventurers, business travelers, and furry friends (pets). -Note: Stairs to the 2nd floor are steep: guests are responsible for child safety.

The Writer's Cottage
The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and ironwork table.

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 relax by the firepit- we hope you enjoy your stay and will visit us again.

Cozy Guesthouse Near Downtown, Lee
Welcome and enjoy our renovated Guesthouse at Lee, MA, staying on main street (15 minutes from Great Barrington and 20 minutes from Pittsfield). It is also 3 mins to Outlet and 19 mins to the closest Ski area.The master bedroom has a queen size soft mattress, and the second bedroom has a queen bed also. The kitchen has a brand new refrigerator, a gas range, and units for cooking. You will enjoy the comfortable stay! Owners live upstairs and be friendly to all visits.

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.

Relaxing secluded stay with loving social animals.
Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door. Just Added mini split AC!

The Cottage at The Barrington House
Welcome to the Cottage at the Barrington House! The Barrington House is nestled in the serene Berkshires Mountains - which have long been a sanctuary for weary city dwellers seeking breathing space, a perfect retreat for artists, writers and thinkers! It's sprawling grounds offer stunning views of lush valleys and distant peaks, while the interior features a fireplace, cozy reading nook, and unlimited windows that invite the natural world inside.

Modern studio with views of the treetops
Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

Stylish Mid-century Modern Berkshires Cape
Stylish and design forward, yet entirely comfortable for families and kids. Fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires. 15 minutes from Butternut ski to south + Bousquet to the north, 35 min to Jiminy Peak. Cozy up by the wood burning fireplace and enjoy the winter wonderland! The house is decorated in mid century modern style with gorgeous design touches throughout!

Station House 1E Private Room & Bath
Our place is a central location in Berkshire County, short drive to restaurants and shops; art and culture, skiing and hiking also close by. You’ll love this former train station( next to the Housatonic RR tracks) which is on three acres between a chapel, the scenic Housatonic River and October Mountain. Our place is good for couples, solo adventurers, and business travelers.
Popular amenities for Lee family-friendly rentals
Family-friendly home rentals with a hot tub

Artist Cottage

Log Cabin: Amazing Views, River Frontage, Hot Tub

“Hickory” Rustic Cabin Retreat with Fireplace

Beautiful Timber Frame Retreat

The Creation Station

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

Cabin in the woods w cedar Hot Tub + private pond

Jaw dropping mountain & lake views
Family- and pet-friendly home rentals

Dancing Horse Lodge

Carriage house with Chef's Kitchen, close to town

Net Zero home with rustic Berkshire charm

The Beer Diviner Brewery Apartment

Modern Copake Falls Getaway - 8 Mins to Catamount

Enjoy every season the Berkshires have to offer.

Berkshire Treehouse Retreat

Cottage on Scenic Road
Family-friendly home rentals with a pool

Cozy Cottage near lake

Near Saratoga – King Bed, Tub, Fire Pit & Movies

Eco Cottage in the Woods

Modern Upstate Cabin, near Rhinebeck NY

Luxe 1822 Apt | Rain Shower | Plush beds | Firepit

Country Getaway Tiny House in Woods w/Pool/Sauna.

Le Soleil Suite - Fire pit, Views 10 Min To Hudson

Skylights, art + design in best downtown location
When is the best time to visit Lee?
Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
---|---|---|---|---|---|---|---|---|---|---|---|---|
Avg. price | R4,341 ZAR | R4,048 ZAR | R4,444 ZAR | R4,341 ZAR | R4,651 ZAR | R5,185 ZAR | R5,667 ZAR | R5,512 ZAR | R4,995 ZAR | R4,944 ZAR | R4,823 ZAR | R4,909 ZAR |
Avg. temp | -3°C | -1°C | 3°C | 10°C | 16°C | 20°C | 24°C | 23°C | 18°C | 12°C | 6°C | 0°C |
Quick stats about vacation rentals that are family-friendly in Lee
Total rentals
190 properties
Nightly prices starting at
R1,723 ZAR before taxes and fees
Total number of reviews
6.7K reviews
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
70 properties have a pool
Rentals with dedicated workspaces
90 properties have a dedicated workspace
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- Family-friendly rentals Berkshire County
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Kent Falls State Park
- Zoom Flume
- Catamount Mountain Ski Resort
- Bushnell Park
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Wintonbury Hills Golf Course
- Taconic State Park
- Mount Sugarloaf State Reservation
- Opus 40
- Mohawk Mountain Ski Area
- Beartown State Forest
- Mount Tom State Reservation
- Mount Snow Ski Resort
- Bousquet Mountain Ski Area
- Hartford Golf Club
- Bright Nights at Forest Park
- Albany Center Gallery
- Talcott Mountain State Park