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Our top choices for Lenox vacation homes

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
The price is CA $205
CA $509 total
includes taxes & fees
Jun 8 - Jun 9
stylish Berkshires Retreat

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is CA $661
CA $1,198 total
includes taxes & fees
Jun 16 - Jun 17
Spacious 5-bedroom house in charming Lee with WiFi

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is CA $203
CA $523 total
includes taxes & fees
Jun 10 - Jun 11
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is CA $131
CA $475 total
includes taxes & fees
Jun 17 - Jun 18
Real Estate: Therapy - Lake, Laundry, Love it

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is CA $223
CA $548 total
includes taxes & fees
Jun 7 - Jun 8
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (15 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is CA $282
CA $437 total
includes taxes & fees
Jun 9 - Jun 10
Cozy Riverside Berkshires Retreat

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (32 reviews)
"Everything was as advertised!"
United States
Jessica S.
The price is CA $332
CA $507 total
includes taxes & fees
Jun 16 - Jun 17
Home in Great Barrington

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is CA $243
CA $783 total
includes taxes & fees
Jun 8 - Jun 9
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is CA $202
CA $534 total
includes taxes & fees
Jun 7 - Jun 8
Near Tanglewood: Historic Summer Retreat

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (25 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is CA $282
CA $627 total
includes taxes & fees
Jun 8 - Jun 9
North Getaway Cottage

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is CA $401
CA $816 total
includes taxes & fees
Jun 8 - Jun 9
Treetop Hideaway in Tyringham

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.6 out of 10, Exceptional, (5 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is CA $278
CA $478 total
includes taxes & fees
Jun 7 - Jun 8
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"Kind and responsive host."
United States
Javier
The price is CA $224
CA $759 total
includes taxes & fees
Jun 7 - Jun 8
Comfortable Berkshires retreat on mtn resort, SISO

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (2 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is CA $341
CA $787 total
includes taxes & fees
Jun 8 - Jun 9
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is CA $329
CA $701 total
includes taxes & fees
Jun 10 - Jun 11
Cheerful 3-bedroom cottage with woodstove

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is CA $223
CA $561 total
includes taxes & fees
Jun 8 - Jun 9
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is CA $417
CA $742 total
includes taxes & fees
Jun 7 - Jun 8
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is CA $385
CA $693 total
includes taxes & fees
Jun 16 - Jun 17
Walk to Williams * Steam Sauna * Ritz-Carlton Bed

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
8.0 out of 10, Very good, (1 review)
"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "
United States
Luz A.
The price is CA $228
CA $568 total
includes taxes & fees
Jun 7 - Jun 8
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is CA $436
CA $770 total
includes taxes & fees
Jun 8 - Jun 9
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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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Top Lenox Hotel Reviews

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Lenox Vacation Homes information

Number of reviews
14,553
Accommodation
439 Vacation Homes
Lowest Price
CA $104
Highest Price
CA $315

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