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Compare 360 Vacation Homes in Lenox with updated reviews, rates, and availability.

Waterview Home in the Berkshires: Near Hiking
Sheffield Vacation Rental | 3BR | 2BA | 2,262 Sq Ft | 2 Steps to Enter
Waterview Home in the Berkshires: Near Hiking
9.2 out of 10, Wonderful, (14)
"Lovely house and kind owner. We had a great time. The view is amazing."
Waterview Home in the Berkshires: Near Hiking
Private Lake House in the Berkshires
Lake Side
Private Lake House in the Berkshires
9.8 out of 10, Exceptional, (15)
"This was our first VRBO experience, and we are hooked. We had a wedding in Pittsfield with events over three days, so we decided to try this lakeside retreat, and it was a treat! The Berkshires in the fall are absolutely beautiful and Hinsdale is a pretty little town. Ozzie's is definitely worth the trip for breakfast. The lake is lovely and we were looking forward to kayaking and fishing. Unfortunately the weather was not on our side, but we still got one fish! Mary is a wonderful host who is...
Private Lake House in the Berkshires
Cozy Retreat on Copake Lake in our Charming Home
Front of the house
Cozy Retreat on Copake Lake in our Charming Home
9.6 out of 10, Exceptional, (32)
"Great stay. A short walk to everything the lake has to offer."
Cozy Retreat on Copake Lake in our Charming Home
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COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Living area
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, (7)
"We had a great stay while skiing for 2 days at nearby Catamount ski resort. The kitchen and house were fully stocked with all essentials. Netflix access enabled us to enjoy a family movie after a long day of skiing. Cozy house and quiet area.......nice to wake up to hear birds chirping!!"
The price is AED 584
AED 1,229 total
includes taxes & fees
1 Jul - 2 Jul
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Heated pool
Peaceful Retreat Compound 10 Minutes to Great Barrington!
10.0 out of 10, Exceptional, (11)
"The property was fabulous and had lots of activities on site(basketball hoops,pickleball court and pool). Excellent location close to Great Barrington downtown which has an amazing selection of restaurants. Overall,fantastic stay!"
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Spectacular views and close to Great Barrington.
Private kitchen
Spectacular views and close to Great Barrington.
Spectacular views and close to Great Barrington.
Tranquil 3-BR Waterfront Retreat
HRDSC00175.jpg
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, (7)
"The house is immaculate! One of the cleanest properties we've stayed in. The house was the perfect size for my family of 4 (2 adults, 2 teens) with room for more. The beds are comfortable, and there were plenty of linens and towels. The linens and towels are high quality, very soft. The kids had fun fishing in the pond and made good use of the kayak (they caught some bass, pickerel and sun fish). The neighborhood is nice and quiet, dirt roads, no traffic...great for taking walks. We used the...
Tranquil 3-BR Waterfront Retreat
Hearts Desire is a furnished whole house in a small, colorful garden center.
Exterior
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, (68)
"What an amazing find to stay at while attending a yoga festival at Jiminy Peak. The house was immaculate and didn't miss a thing! Not only was there a bottle of wine waiting, but an adorable history of the home. The house was HUGE and the beds very comfortable. I wouldn't call it a 3 bedroom house though, it's a 2 bedroom with a pull out sofa in the living room. The hot tub is amazing and watching the starts and fireflies in the backyard at night was magical. Highly recommend and would stay...
Hearts Desire is a furnished whole house in a small, colorful garden center.
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Exterior
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
10.0 out of 10, Exceptional, (25)
"Beautiful property- well maintained and excellent location."
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo
Comfortable New Decor in Living Room Equipped w Smart TV and Deck
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo
9.8 out of 10, Exceptional, (59)
"Worked well for our small team. Close enough to the base area to walk."
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (8)
"I really loved my stay at this beautiful property surrounded by nature and peacefulness in the Berkshire mountains. The owners were great too with communication and making things easy for check in and check out. Highly recommend this place!"
Pristine Home In Becket Woods
Peace and quiet on the lake
Exterior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (186)
"The house was clean and cozy. The kitchen was well stocked, especially important as we like to cook at home. Justin was responsive when I contacted him with questions. Love that the house was dog friendly with a fenced in back yard. The house has been updated inside but the deck needs some TLC, which I am sure are in the plans. A perfect get away!"
Peace and quiet on the lake
Chic Pittsfield Home With A View!
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
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!
8.8 out of 10, Excellent, (3)
"My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!"
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Fully stocked newly renovated Kitchen.
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, (93)
"Everything is basic but solid and comfortable. Beds were nice and firm, my preference. Host was lovely. Wish we could have stayed longer to explore the area more."
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
We're ready for Spring & Summer in Upstate NY!
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
10.0 out of 10, Exceptional, (2)
"The barn was amazing and just perfect for our weekend away. Ricky was really great to communicate with and very responsive. We can’t wait to go again soon!"
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Private Access To Laurel Lake, Enjoy Lake Life
Private Access To Laurel Lake, Enjoy Lake Life
10.0 out of 10, Exceptional, (6)
"My brother and I came to honor our late father, our family used to own property on Laurel lake so it was especially meaningful to us to have access to it for kayaking. The house has central ac which is harder to find, it's got plenty of bedrooms, two of which are on the first floor."
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."
The price is AED 2,828
AED 4,969 total
includes taxes & fees
6 Jul - 7 Jul
Private Cabin On Over 12 Acres Of Woods!
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Beautiful open concept for Entertaining friends and family
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
10.0 out of 10, Exceptional, (107)
"Our party of four adults found ample space to spread out and relax at this property. There are quite a few stairs to access all three stories, including the main living space on the second story and the four bedrooms on the third story. The kitchen is well equipped and there is a charcoal grill (bring your own charcoal). There is a very nice deck overlooking the lovely and sprawling grounds below the house. A fire pit was situated behind the house. There is a balcony and patio also off the...
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB
Truly nestled on 5+ acres and LESS than 0.8miles to downtown Great Barrington
Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB
10.0 out of 10, Exceptional, (12)
"This was a great house! They thought of all the details, had everything you could need. Hot tub was clean and entire house was spotless. Beds were comfortable. Great location, so close to downtown Great Barrington, cute shops and restaurants. And also super close to lots of hikes and ski mountain etc. We had a really fantastic stay and would stay again and recommend!"
Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB
Don't see what you're looking for?
See all available properties in Lenox
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.

Other property types in Lenox

Fox Hollow Luxury Ranch Laurel Lake
Property grounds
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
The Kemble- Built by a US Secretary of State in Lenox
The Kemble - a registered Great Estate
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (15)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox
Amore Estate - sleeps 12 in beds
October MNT FARM!!
Amore Estate - sleeps 12 in beds
9.6 out of 10, Exceptional, (8)
"Great space for a group of friends! House has a lot of character. Beautiful property and great location! Easy access to downtown Lenox and surrounding area. We really enjoyed our stay!"
Amore Estate - sleeps 12 in beds
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.

Recent reviews of Lenox hotels
Expedia verified reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

5/5 Excellent
"We enjoyed our stay, played mini golf, swam and used the arcade. There were a lot of activities and amenities to choose from. Well kept property. "
A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Posted 15 hours ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel