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Holiday Rentals in Lenox

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50 rentals in Lenox.
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Gartner House, a charming home in Lenox, holiday rental in Lenox

Gartner House, a charming home in Lenox

4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Warm your heart this holiday season in this cozy cottage next to downtown Lenox., holiday rental in Lenox

Warm your heart this holiday season in this cozy cottage next to downtown Lenox.

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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RANKED #1 for 5 STAR REVIEWS covering 355 properties., holiday rental in Lenox

RANKED #1 for 5 STAR REVIEWS covering 355 properties.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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5 STAR! Lenox. Luxury. Location., holiday rental in Lenox

5 STAR! Lenox. Luxury. Location.

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood, holiday rental in Lenox

Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Heart of Lenox Walk to Town Cozy Cottage!, holiday rental in Lenox

Heart of Lenox Walk to Town Cozy Cottage!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Heart of Lenox, holiday rental in Lenox

Heart of Lenox

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE, holiday rental in Lenox

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Berkshires Home w/Kayak - Walk to Stockbridge Bowl, holiday rental in Lenox

Berkshires Home w/Kayak - Walk to Stockbridge Bowl

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Restored 1881 Farm House, holiday rental in Lenox

Restored 1881 Farm House

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Fox Hollow Laurel Lake Ranch, holiday rental in Lenox

Fox Hollow Laurel Lake Ranch

4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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Private Guest House in Dtwn Lenox, Walk to Dining!, holiday rental in Lenox

Private Guest House in Dtwn Lenox, Walk to Dining!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful, secluded, private resort in the heart of the Berkshires in Lenox, MA, holiday rental in Lenox

Beautiful, secluded, private resort in the heart of the Berkshires in Lenox, MA

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Lenox Home, 3 Mi to Shakespeare & Co!, holiday rental in Lenox

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!, holiday rental in Lenox

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

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Recently renovated 4 bedroom lakefront house in The Berkshires., holiday rental in Lenox

Recently renovated 4 bedroom lakefront house in The Berkshires.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town., holiday rental in Lenox

4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town.

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Newly Renovated 1910 Farmhouse - Walk To Town - Perfect Berkshire Retreat, holiday rental in Lenox

Newly Renovated 1910 Farmhouse - Walk To Town - Perfect Berkshire Retreat

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Lovingly restored Victorian in Lee's Historic District **Spring:3rd nt 1/2 off, holiday rental in Lenox

Lovingly restored Victorian in Lee's Historic District **Spring:3rd nt 1/2 off

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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General Williams Estate House Lenox/Stockbridge, holiday rental in Lenox

General Williams Estate House Lenox/Stockbridge

6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special, holiday rental in Lenox

Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Freckled Hen's Berkshire Nest, holiday rental in Lenox

The Freckled Hen's Berkshire Nest

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming 1860 Farmhouse, Completely Renovated, Convenient Location, Central AC, holiday rental in Lenox

Charming 1860 Farmhouse, Completely Renovated, Convenient Location, Central AC

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b, holiday rental in Lenox

Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Charming Farmhouse Steps from Downtown West Stockbridge, holiday rental in Lenox

Charming Farmhouse Steps from Downtown West Stockbridge

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Grand Colonial Home in the Heart of The Berkshires, holiday rental in Lenox

Grand Colonial Home in the Heart of The Berkshires

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Elegant 19th Century New England Newly Renovated 1BR Vacation Rental, holiday rental in Lenox

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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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2 Bedroom newly renovated townehouse, beautifully decorated at Garfield House, holiday rental in Lenox

2 Bedroom newly renovated townehouse, beautifully decorated at Garfield House

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautifully Restored 1820s Industrial Loft Living On A Creek, holiday rental in Lenox

Beautifully Restored 1820s Industrial Loft Living On A Creek

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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SPECTACULAR RENOVATED BERKSHIRE LAKEFRONT HOUSE ON RICHMOND POND, holiday rental in Lenox

SPECTACULAR RENOVATED BERKSHIRE LAKEFRONT HOUSE ON RICHMOND POND

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Family-friendly Cottage Near Lake, Tanglewood, holiday rental in Lenox

Family-friendly Cottage Near Lake, Tanglewood

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Sophisticated &  Comfortable Stockbridge Retreat  A+ Location  Modern Amenities, holiday rental in Lenox

Sophisticated & Comfortable Stockbridge Retreat A+ Location Modern Amenities

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Garfield House Studio at 208, holiday rental in Lenox

Garfield House Studio at 208

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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CABIN FEVER IN STOCKBRIDGE, holiday rental in Lenox

CABIN FEVER IN STOCKBRIDGE

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Artist's Cottage on the Lake Mahkeenac, holiday rental in Lenox

Artist's Cottage on the Lake Mahkeenac

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stockbridge Bowl Lake Community, holiday rental in Lenox

Stockbridge Bowl Lake Community

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Lake House, holiday rental in Lenox

Lake House

5 bedrooms
6 bathrooms
Sleeps 9
Match: Sleeps
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Berkshires Spacious Comfortable Charming Farmhouse, holiday rental in Lenox

Berkshires Spacious Comfortable Charming Farmhouse

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Garfield House, holiday rental in Lenox

Garfield House

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Vacation Home on 10 Acres with Pool and Spa, holiday rental in Lenox

Vacation Home on 10 Acres with Pool and Spa

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Iris Room, holiday rental in Lenox

Iris Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Horse Room, holiday rental in Lenox

Horse Room

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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One of the Finest Homes and Best location in the Berkshires, holiday rental in Lenox

One of the Finest Homes and Best location in the Berkshires

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Spacious, Lake View Condo Near Tanglewood in the Heart of the Berkshires!, holiday rental in Lenox

Spacious, Lake View Condo Near Tanglewood in the Heart of the Berkshires!

4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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The Gatehouse on Golden Hill, holiday rental in Lenox

The Gatehouse on Golden Hill

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Berkshires Summer Rental -  Lee/Lenox, holiday rental in Lenox

Berkshires Summer Rental - Lee/Lenox

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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** Private Berkshire Escape** Monthly Pricing Available, holiday rental in Lenox

** Private Berkshire Escape** Monthly Pricing Available

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Cozy Stockbridge Cabin - Walk to Beach & Lake!, holiday rental in Lenox

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Apartment Newly Remodeled Super Location, holiday rental in Lenox

Apartment Newly Remodeled Super Location

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh, holiday rental in Lenox

Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh

3 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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