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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.
9.8 out of 10, Exceptional, (16)
"Clean, house has plenty of room. Lovely property. "
Amore Estate - beautiful room with many places to explore and relax in.
Secluded Family Home in Serene Stockbridge Woods
10.0 out of 10, Exceptional, (18)
"Beautiful home cozy clean great setting 15-20 mins to all of our fav locations Stockbridge, Lenox, Great Barrington and hiking trails. House was well appointed and very comfortable. The kids had plenty to do, great selection of kids book and fun murals and scenery painted throughout the home. We are look in g forward to heading back next season. Tom and Susanna were great and very responsive with all communications. Thank you& see you soon!"
Secluded Family Home in Serene Stockbridge Woods
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!!
9.8 out of 10, Exceptional, (218)
"The room was beautiful. A lot of thought was put into what you would need during your stay. The location was convenient to a lot of sights, biking and restaurants. I would definitely stay again. "
The price is SAR 537
SAR 826 total
includes taxes & fees
11 Nov 2024 - 12 Nov 2024
Berkshire Village Carriage House - Super Private!!
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
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!
9.4 out of 10, Exceptional, (35)
"The home is very nice and cozy. It really felt like a comfy home."
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee
10.0 out of 10, Exceptional, (4)
"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!
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
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
10.0 out of 10, Exceptional, (6)
"The host, Samantha, was ideal! She was communicative, accomodating, and attentive. The place was perfect, right in the heart of town"
The price is SAR 2,441
SAR 4,011 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
Find your Sanctuary at The Rectory at Stockbridge
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
10.0 out of 10, Exceptional, (12)
"Great location, feels remote but quick drive to everything. Enjoyed the house, clean and great space. A couple glitches that were quickly resolved by caretakers. "
Private Access To Laurel Lake, Enjoy Lake Life
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
10.0 out of 10, Exceptional, (87)
"Very roomy and charming. We didn’t get to stay long as we were in town for an event - we hope to be back. Location allows for walking to anywhere in town. Jeff is accommodating and responsive, ample parking. No issues."
Elegant 19th Century New England 2BR vacation rental at Garfield House
Stockbridge Home: Walk to Town Beach!
9.8 out of 10, Exceptional, (9)
"Clean and cozy and perfectly situated to explore the Berkshires on a long weekend"
Stockbridge Home: Walk to Town Beach!
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10.0 out of 10, Exceptional, (17)
"At the end of a dead-end street but only two blocks from the center of Stockbridge, this century-old charmer may be the best-kept and best-supplied rental in the Berkshires. We stayed a month(!) and loved it. The location is unbeatable, an easy walk from the Red Lion and within 15 minutes of Tanglewood, The Mount, the Rockwell museum and other attractions. Four local trails begin 100 feet away, including the Ice Glen. A beautiful, productive garden awaits, and the screened front porch may be...
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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
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!
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
3.0 star property
8.6 out of 10, Excellent, (1737)
"The staff was very nice! And the room was spacious and clean with plenty of amenities. "
The price is SAR 634
SAR 733 total
includes taxes & fees
7 Nov 2024 - 8 Nov 2024
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (912)
"Very quiet and clean. would definitely go back. "
The price is SAR 560
SAR 614 total
includes taxes & fees
7 Nov 2024 - 8 Nov 2024
Jiminy Peak Mountain Resort
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.