Lee, Massachusetts

Vacation Rentals in Lee, Massachusetts

Discover 22 vacation rental properties in Lee. From 1 to 6 bedrooms. Average $414/night. 100% have pools.

22 verified listings Book securely on VRBO Prices updated March 2026

22 properties available

Centrally Located Historical Home

Centrally Located Historical Home

2 beds 3 baths
PoolA/CWiFiBalcony
$320/night
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Historic 1817 Berkshire Farmhouse- Close to Everything!

Historic 1817 Berkshire Farmhouse- Close to Everything!

1 bed 1 bath
PoolA/CWiFiBalcony
$276/night
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Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

1 bed 1 bath
PoolA/CWiFiBalcony
$126/night
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Garfield Townhouse in the Berkshires on Main St

Garfield Townhouse in the Berkshires on Main St

2 beds 1 bath
PoolA/CWiFiBalcony
$145/night
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Lakeview Retreat - mins. to downtown Lenox, Stockbridge, Lee

Lakeview Retreat - mins. to downtown Lenox, Stockbridge, Lee

3 beds 3 baths
PoolA/CWiFiBalcony
$559/night
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The Playhouse: 7,000 Square Feet of Berkshires Modern Luxury and History

The Playhouse: 7,000 Square Feet of Berkshires Modern Luxury and History

6 beds 5 baths
PoolA/CWiFiBalcony
$1,090/night
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Relax between your Berkshire adventures! Easy walk to town! Centrally located!

Relax between your Berkshire adventures! Easy walk to town! Centrally located!

3 beds 1 bath
PoolA/CWiFiBalcony
$353/night
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Lovely Lakefront Cottage, Peaceful Setting, Hiking And More

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More

2 beds
PoolA/CWiFiBalcony
$287/night
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Elegant 19th Century New England 2BR vacation rental at Garfield House

Elegant 19th Century New England 2BR vacation rental at Garfield House

2 beds 1 bath
PoolA/CWiFiBalcony
$201/night
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Modern And Spacious Berkshires Retreat 5 bdrm 3 bath

Modern And Spacious Berkshires Retreat 5 bdrm 3 bath

5 beds 3 baths
PoolA/CWiFiBalcony
$526/night
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Berkshires Home Makeover ~ Immaculate Lakefront Getaway ~ Dreamy Sunsets!

Berkshires Home Makeover ~ Immaculate Lakefront Getaway ~ Dreamy Sunsets!

4 beds 6 baths
PoolA/CWiFiBalcony
$714/night
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1500 sqft private entrance with beautiful views of the Berkshire Mountains

1500 sqft private entrance with beautiful views of the Berkshire Mountains

2 beds
PoolA/CWiFiBalcony
$271/night
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Great Place - 2 BD - Kitchen and Pool

Great Place - 2 BD - Kitchen and Pool

2 beds 2 baths
PoolA/CWiFiBalcony
$197/night
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Holiday Inn Oak n' Spruce Resort -1BD Sleeps up to 4

Holiday Inn Oak n' Spruce Resort -1BD Sleeps up to 4

1 bed 1 bath
PoolA/CWiFiBalcony
$244/night
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Garfield Gallery 2 BR in the Annex

Garfield Gallery 2 BR in the Annex

1 bed 1 bath
PoolA/CWiFiBalcony
$135/night
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Spectacular setting on your own private lake close to it all!

Spectacular setting on your own private lake close to it all!

4 beds 3 baths
PoolA/CWiFiBalcony
$551/night
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Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!

Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!

5 beds 3 baths
PoolA/CWiFiBalcony
$766/night
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Berkshire Manor for Lasting Memories. 5 Bedrooms. 5 Full Bathrooms.

Berkshire Manor for Lasting Memories. 5 Bedrooms. 5 Full Bathrooms.

5 beds 5 baths
PoolA/CWiFiBalcony
$592/night
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Fox Hollow Luxury Ranch Laurel Lake

Fox Hollow Luxury Ranch Laurel Lake

4 beds 4 baths
PoolA/CWiFiBalcony
$551/night
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*Special rate for any June dates remaining!*

*Special rate for any June dates remaining!*

4 beds 4 baths
PoolA/CWiFiBalcony
$640/night
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Great Place - 2 BD - Kitchen - Pool

Great Place - 2 BD - Kitchen - Pool

2 beds 2 baths
PoolA/CWiFiBalcony
$197/night
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Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

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

5 beds 3 baths
PoolA/CWiFiBalcony
$375/night
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