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Compare 469 Vacation Homes in Lenox with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is SAR 563
SAR 859 total
includes taxes & fees
22 Mar - 23 Mar
Berkshire Village Carriage House - Super Private!!

Peace and quiet on the lake

9.6 out of 10, Exceptional, (211)
"Property was very nice. Quite area. Host was fantastic. "
Peace and quiet on the lake

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is SAR 2,059
SAR 3,758 total
includes taxes & fees
21 Mar - 22 Mar
Hancock Village Inn at Jiminy Peak

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (45)
"We had an amazing long ski weekend at the Great Escape Ski Cottage. The listing is very accurate. Great communication with Shay. The house was immaculate upon arrival. The layout of the house was perfect for our family (6 adults and 4 children aged 4-9). One beautiful Master Bedroom on the first floor. Two of the other equally beautiful bedrooms are on the second floor. The linens were hotel quality! The "Kid's Quarters" was located off of the kitchen/laundry room. A playroom with multiple games...
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

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.

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

10.0 out of 10, Exceptional, (1)
"My friends and I stayed at this adorable and HUGE home in this lovely condo complex to spend the weekend at Ski Butternut which was only like 10 minutes away. The host even left us 2 bottles of wine! It had FIVE bathrooms which is unheard of, like anywhere, and the beds were the fancy adjustable kinds. TVs and cable in every bedroom. The fireplace was so luxurious. When the living room TV was giving us some connection issues I think it was a total of like 7 minutes to contact the host/co-host...
Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (69)
"Tom’s cottage was the perfect place for us to stay to enjoy the new year in quiet Lenox. It was centrally located which made exploring town easy and convenient. The check in and out process was super simple and Tom made himself easily accessible throughout the stay. "
Heart of Lenox Walk to Town Cozy Cottage!

Berkshires Lakefront Retreat

10.0 out of 10, Exceptional, (6)
"Outfitted with everything a guest could want or need, from a fully equipped kitchen, linens, and cozy afghans to marshmallows for the hot chocolate. Spacious house with lots of places to gather or spread out. Beautiful setting—snow covered frozen lake. We would love to return in warm weather to make use of the lakefront. Very responsive and considerate host. "
Berkshires Lakefront Retreat

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

10.0 out of 10, Exceptional, (24)
"Beautiful, remote property perfect for large groups! We'll definitely try get back there in the summer!"
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Perfect Nature Retreat In Great Barrington

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great time at the house. We had everything we needed. It was close to town. The space is very comfortable."
Perfect Nature Retreat In Great Barrington

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (5)
"Lovely ski weekend! Best memory: hot tubbing at sunset after skiing with snow falling all around! "
Mountain Blossom Retreat by Evergreen Home

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

9.4 out of 10, Exceptional, (8)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Comfortable Berkshires retreat on mtn resort, SISO

The price is SAR 604
SAR 1,818 total
includes taxes & fees
2 Apr - 3 Apr
Comfortable Berkshires retreat on mtn resort, SISO

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (19)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is SAR 506
SAR 1,278 total
includes taxes & fees
24 Mar - 25 Mar
Near Tanglewood: Historic Summer Retreat

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

10.0 out of 10, Exceptional, (149)
"The location is beautiful and there are lots of places to visit in the area. The house is nice; great view of Otis Reservoir. It took us a while to figure out the multiple thermostats, but it was a good Christmas house. The owner was nice enough to allow us to have a Christmas tree, and had someone make an extra trash pick up for us after Christmas.The one thing we were disappointed in was the cleanliness. Shower curtains were moldy, some of the dishes weren't very clean, expired condiments...
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (10)
"We all enjoyed our stay. The house and indoor pool were wonderful. There are plenty of comfortable places to sit and enjoy the gorgeous views. We loved the location which is both close to Lenox restaurants, as well as, the southern Berkshires for food markets and activities for kids. The property manager was attentive, and the owner was very responsive. We loved our week at this family friendly property and highly recommend it. "
Wellspring by AvantStay | Indoor Pool + Views

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

10.0 out of 10, Exceptional, (120)
"Fantastic home! Clean, well stocked and very comfortable. We had a great time and will be back. The owner was kind, considerate and appreciative of our stay. Thanks again! "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

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

9.0 out of 10, Wonderful, (23)
"The property is great for a group of people lots of bedrooms. Lots of sitting rooms. The kitchen is great for a culinary event - we had a private chef one night. The upstairs den was very cozy-It was a cold weekend with lots of snow- we didn’t want to leave the house !And close to Lenox -and Miraval spaWe would definitely come back next year. "
Amore Estate - beautiful room with many places to explore and relax in.

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.6 out of 10, Exceptional, (41)
"Very clean place. Decorated like your grandmother's house. Homey. And you get to use the garage--a big help on a snowy weekend. If you want convenience and cleanliness, this is a great spot. If you want quiet--skip. It's right on Rt. 7 and you have lots of traffic moving by at high speeds. But to their credit, there are many sound machines to drown it out. "
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (39)
"We had a wonderful time -- the bedrooms were so comfortable, the kitchen had everything we needed, and when we got snowed in, the owners and neighbors were incredibly helpful. Thank you!"
Beautiful Berkshire Farm House on 160+ 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.
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Other property types in Lenox

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow

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

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

10.0 out of 10, Exceptional, (1)
"My friends and I stayed at this adorable and HUGE home in this lovely condo complex to spend the weekend at Ski Butternut which was only like 10 minutes away. The host even left us 2 bottles of wine! It had FIVE bathrooms which is unheard of, like anywhere, and the beds were the fancy adjustable kinds. TVs and cable in every bedroom. The fireplace was so luxurious. When the living room TV was giving us some connection issues I think it was a total of like 7 minutes to contact the host/co-host...
Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate
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.