
Vacation rentals in Lee
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Top-rated vacation rentals in Lee
Guests agree: these stays 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

The Coach House | Modern 2BR Loft + Views & Pool
Restored coach barn with 25-ft cedar ceilings, skylights, and mountain views—part of House on Golden Hill, a historic Lenox farmhouse compound. This airy 2BR + loft retreat blends rustic charm with modern ease. Enjoy a full kitchen, cozy living space, and outdoor area. Set beside a stream with seasonal pool access, it’s perfect for families, couples, or creative escapes. Centrally located and just minutes to downtown Lenox, Tanglewood, and trails—your Berkshires base for rest and inspiration.

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.

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.

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(will consider pets.)(90 second walk through wooded path to lake)

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!

Berkshire cabin with scenic foliage views
The Beaver Dam is a sunlight-filled & recently renovated cabin tucked in the woods, overlooking the October Mountain State Park and steps away from Basin Pond. We are located close to a number of excellent ski slopes. Our cottage is the last house on a private road and right next to protected forest. You can't ask for more privacy, peace and quiet than you'll find at our little piece of paradise on the pond!
Popular amenities for Lee vacation rentals
Other great vacation rentals in Lee

The Blue Jay Cottage

Spacious & Family-Ready Home w/ Fenced Yard in Lee

Newly Renovated, and Spacious great for family

Upstairs on Main

Stockbridge private apartment

HawksNest: quiet 2BR apt, heart of the Berkshires

Hot Tub, Canoe, Hike, Dog Friendly, Berkshires!

Bungalow in the Berkshires
Frequently Asked Questions
Are there family-friendly vacation rentals in Lee?
Lee has more than 180 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Lee?
Enhance your stay in our House Rentals with the most popular amenities: over 100 homes with air conditioning, over 100 homes with a kitchen, over 110 homes with wifi, over 110 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Lee?
Four-legged friends are welcome in Lee. Choose from more than 70 vacation rentals for guests traveling with pets.
Do aparthotel rentals in Lee have air conditioning?
Absolutely! We offer over 20 aparthotel rentals with air conditioning in Lee. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Lee?
Experience the best of Lee with our apartment rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Lee?
Yes! Work meets play with ease at over 130 vacation rentals in Lee featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Lee have free parking?
Absolutely! We offer over 110 house rentals with free parking in Lee. Enjoy a tailored experience with all the comforts you desire.
Do aparthotel rentals in Lee have a kitchen?
Absolutely! We offer over 20 aparthotel rentals with a kitchen in Lee. Enjoy a tailored experience with all the comforts you desire.
Are there Lee vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 80 vacation homes with pools in Lee, available on Airbnb. Make a splash and soak up the sun in style!
Do boutique hotel rentals in Lee have wifi?
Absolutely! We offer over 20 boutique hotel rentals with wifi in Lee. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Lee
Total vacation rentals
Explore 290 vacation rentals in Lee
Nightly prices starting at
Lee vacation rentals start at $10 per night before taxes and fees
Verified guest reviews
Over 10,440 verified reviews to help you choose
Family-friendly vacation rentals
190 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 70 rentals that welcome pets
Vacation rentals with a pool
90 properties feature pools
Rentals with dedicated workspaces
140 properties have a dedicated workspace
Wi-Fi availability
280 of Lee vacation rentals include wi-fi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Lee rentals
4.9 Average rating
Lee stays are highly rated by guests—averaging 4.9 out of 5!
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- 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
- Mount Greylock Ski Club
- Zoom Flume
- Catamount Mountain Ski Resort
- Bushnell Park
- Norman Rockwell Museum
- Taconic State Park
- Wintonbury Hills Golf Course
- Hartford Golf Club
- Bright Nights at Forest Park
- Mount Tom State Reservation
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Opus 40
- Beartown State Forest
- Talcott Mountain State Park
- Albany Center Gallery
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