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Compare 114 Vacation Homes in Lee with updated reviews, rates, and availability.

Amore Estate - beautiful room with many places to explore and relax in.
October MNT FARM!!

Amore Estate - beautiful room with many places to explore and relax in.

9.8 out of 10, Exceptional, (17)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
Secluded Family Home in Serene Stockbridge Woods
Living area

Secluded Family Home in Serene Stockbridge Woods

10.0 out of 10, Exceptional, (18)
"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."
Secluded Family Home in Serene Stockbridge Woods
Spectacular views and close to Great Barrington.
Private kitchen

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is AED 525
AED 812 total
includes taxes & fees
25 Nov - 26 Nov
Berkshire Village Carriage House - Super Private!!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Breakfast Nook - wake up to the best sunshine ever!

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Tranquil 3-BR Waterfront Retreat

Tranquil 3-BR Waterfront Retreat

9.8 out of 10, Exceptional, (10)
"Very clean and nicely decorated. Comfortable vibe. Came to relax and enjoy the fall colors. It looks bigger in the pictures, but was plenty big for the 4 of us. Having laundry was a plus, and enjoyed the ping pong table Loved the duvet covers…so soft. Upstairs bathroom could use a mirror in a better place, as blow drying hair and putting on makeup would be difficult, but just didn’t bother. Hope to go again next fall. "
Tranquil 3-BR Waterfront Retreat
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Lenox Vacation Rental | 3BR | 2BA | 2,457 Sq Ft | Step-Free Access

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (36)
"Fun girl’s weekend in the Berkshires! We will be back! Loved the rental and had lots of space! Beds were comfy and we had a great time. "
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee
Cozy living room nestled between the oversized kitchen and four-season porch.

4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee

9.6 out of 10, Exceptional, (5)
"This house had everything one could need for a quick getaway or longer stay. It was very comfortable and situated conveniently to Lee, Lenox and Stockbridge. We spent 3 days exploring and found many things to do. I expect to return and we would rent this house again in a heartbeat."
4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
Sunroom

Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!

10.0 out of 10, Exceptional, (2)
"Delightful property, worked well for our needs"
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
Wellspring by AvantStay | Indoor Pool + Views
Welcome!

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (8)
"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."
Wellspring by AvantStay | Indoor Pool + Views
Find your Sanctuary at The Rectory at Stockbridge
Exterior

Find your Sanctuary at The Rectory at Stockbridge

10.0 out of 10, Exceptional, (6)
"Just a quick stay but a great catch-up. Conveniently located and perfectly clean"
The price is AED 2,387
AED 3,939 total
includes taxes & fees
25 Nov - 26 Nov
Find your Sanctuary at The Rectory at Stockbridge
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
A pictureque outdoor dining table on the patio makes al fresco meals a breeze.

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.2 out of 10, Wonderful, (5)
"The property was spacious and inviting for all of us. The location was perfect. The property manager was very open to suggestions for making some small improvements. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Private Access To Laurel Lake, Enjoy Lake Life

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."
Private Access To Laurel Lake, Enjoy Lake Life
Private Cabin On Over 12 Acres Of Woods!

Private Cabin On Over 12 Acres Of Woods!

9.6 out of 10, Exceptional, (4)
"The property was perfect for our weekend in Becket. The house was very comfortable and the grounds quite beautiful. We enjoyed our visit."
Private Cabin On Over 12 Acres Of Woods!
Elegant 19th Century New England 2BR vacation rental at Garfield House
Exterior

Elegant 19th Century New England 2BR vacation rental at Garfield House

10.0 out of 10, Exceptional, (88)
"Pretty darn perfect but not quite as clean as last year. Maybe different crew?"
Elegant 19th Century New England 2BR vacation rental at Garfield House
Stockbridge Home: Walk to Town Beach!
Stockbridge Vacation Rental | 3BR | 1BA | 1,040 Sq Ft | Stairs Required

Stockbridge Home: Walk to Town Beach!

9.8 out of 10, Exceptional, (10)
"A friend and I stayed at this property when the Trauma Healing Immersion event at Kripalu had them fully booked. As someone who normally stays at Kripalu when attended events I was hesitant to find property close enough to create an experience that was still as full of peace and solace as I am used to. This property was just what the dr. ordered. I love the bathroom remodel! It was quiet and peaceful which was just what we needed after a long day of lecture and experiential training. "
Stockbridge Home: Walk to Town Beach!
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Summer in The Berkshires

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

10.0 out of 10, Exceptional, (18)
"The property was close to town and very cozy, clean & comfortable. Would highly recommend attention to the details was impressive."
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
Open floor plan great for large groups

Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!

10.0 out of 10, Exceptional, (89)
"My family and I loved our stay in Chip and Kim’s lovely post and beam home in Lee. The home was lovely and comfortable for our group of eight, ages two months to 70 years. The home is well-equipped, spacious and charming. Due to the nonstop rain, we were unable to enjoy the gorgeous grounds, but felt very cozy in the fireplaces living room. I highly recommend!"
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
Sunsets On Blue Hill, Newly Renovated Farmhouse

Sunsets On Blue Hill, Newly Renovated Farmhouse

10.0 out of 10, Exceptional, (1)
"The property was really beautiful. Well stocked, well designed and even better than the photos. The owners were incredibly responsive and accommodating. Couldn’t recommend this place more!"
Sunsets On Blue Hill, Newly Renovated Farmhouse
Spacious Historic Home in the Berkshires!
Pittsfield Vacation Rental | 5BR | 2BA | Stairs Required | 3,300 Sq Ft

Spacious Historic Home in the Berkshires!

9.6 out of 10, Exceptional, (5)
"This lovely home was ideal for my family of 8: my children and their spouses, two grandchildren, myself and two pups. The beds were plentiful and comfortable. The house, while old, was newly remodeled, adding modern appliances to the charm of the original building. Very bright and spacious in a quiet neighborhood, convenient to Lenox, Tanglewood, and other special towns. I highly recommend this home to anyone looking for a pleasant retreat. We loved every minute!"
Spacious Historic Home in the Berkshires!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Lee

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1746)
"Property was beautiful, great staff "
The price is AED 620
AED 717 total
includes taxes & fees
25 Nov - 26 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AED 547
AED 600 total
includes taxes & fees
25 Nov - 26 Nov
Jiminy Peak Mountain Resort
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Welcome to The Freeman Berkshires

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.