Lenox, Massachusetts

Vacation Rentals in Lenox, Massachusetts

Discover 19 vacation rental properties in Lenox. From 2 to 5 bedrooms. Average $375/night. 100% have pools.

19 verified listings Book securely on VRBO Prices updated March 2026

19 properties available

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

3 beds 2 baths
PoolA/CWiFiBalcony
$259/night
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Unique Condo, Quiet Neighborhood, Walk to Town.

Unique Condo, Quiet Neighborhood, Walk to Town.

2 beds 2 baths
PoolA/CWiFiBalcony
$165/night
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Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA

Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA

2 beds 1 bath
PoolA/CWiFiBalcony
$271/night
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Heart of Lenox Walk to Town Cozy Cottage!

Heart of Lenox Walk to Town Cozy Cottage!

2 beds 1 bath
PoolA/CWiFiBalcony
$391/night
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51 Church Street, Lenox MA - One Bedroom Unit

51 Church Street, Lenox MA - One Bedroom Unit

1 bath
PoolA/CWiFiBalcony
$409/night
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Restored 1881 Farm House

Restored 1881 Farm House

2 beds 3 baths
PoolA/CWiFiBalcony
$362/night
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5 STAR CASUAL ELEGANCE for 5 STAR GUESTS

5 STAR CASUAL ELEGANCE for 5 STAR GUESTS

3 beds 2 baths
PoolA/CWiFiBalcony
$431/night
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Your Invited to the Berkshires!

Your Invited to the Berkshires!

3 beds 2 baths
PoolA/CWiFiBalcony
$309/night
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Private Access To Laurel Lake, Enjoy Lake Life

Private Access To Laurel Lake, Enjoy Lake Life

4 beds 2 baths
PoolA/CWiFiBalcony
$386/night
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Private Guest House in Dtwn Lenox, Walk to Dining!

Private Guest House in Dtwn Lenox, Walk to Dining!

3 beds 2 baths
PoolA/CWiFiBalcony
$357/night
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Heart of Lenox!! - renovated downtown apartment

Heart of Lenox!! - renovated downtown apartment

2 beds 1 bath
PoolA/CWiFiBalcony
$546/night
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Sophisticated Lenox Retreat by Evergreen Home

Sophisticated Lenox Retreat by Evergreen Home

4 beds 2 baths
PoolA/CWiFiBalcony
$494/night
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Cozy 3BR Home w/ Yard & Patio 5 min to Tanglewood

Cozy 3BR Home w/ Yard & Patio 5 min to Tanglewood

3 beds 2 baths
PoolA/CWiFiBalcony
$305/night
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Enjoy a renovated private home right in downtown Lenox

Enjoy a renovated private home right in downtown Lenox

3 beds 1 bath
PoolA/CWiFiBalcony
$530/night
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Enjoy comfortable elegance in this secluded grand home located in town

Enjoy comfortable elegance in this secluded grand home located in town

5 beds 2 baths
PoolA/CWiFiBalcony
$644/night
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Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!

Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!

2 beds 1 bath
PoolA/CWiFiBalcony
$250/night
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Lenox, private setting, close to Tanglewood rents by month

Lenox, private setting, close to Tanglewood rents by month

3 beds 2 baths
PoolA/CWiFiBalcony
$187/night
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Colonial House, w/Yard,7min walk to Downtown Lenox

Colonial House, w/Yard,7min walk to Downtown Lenox

4 beds 3 baths
PoolA/CWiFiBalcony
$323/night
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48 Main Street, Lenox MA - 48 Main Street, Lenox, MA

48 Main Street, Lenox MA - 48 Main Street, Lenox, MA

2 beds 2 baths
PoolA/CWiFiBalcony
$499/night
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