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Holiday Rentals in Lenox

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58 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, holiday rental in Lenox
 Gartner House, a charming home in Lenox, holiday rental in Lenox

Gartner House, a charming home in Lenox

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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'Village View'- Elegant, Comfortable, Historic Home in Downtown Lenox, holiday rental in Lenox
'Village View'- Elegant, Comfortable, Historic Home in Downtown Lenox, holiday rental in Lenox
'Village View'- Elegant, Comfortable, Historic Home in Downtown Lenox, holiday rental in Lenox

'Village View'- Elegant, Comfortable, Historic Home in Downtown Lenox

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Unique Condo, Quiet Neighborhood, Walk to Town., holiday rental in Lenox
Unique Condo, Quiet Neighborhood, Walk to Town., holiday rental in Lenox
Unique Condo, Quiet Neighborhood, Walk to Town., holiday rental in Lenox

Unique Condo, Quiet Neighborhood, Walk to Town.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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5 STAR CASUAL ELEGANCE for 5 STAR GUESTS, holiday rental in Lenox
5 STAR CASUAL ELEGANCE for 5 STAR GUESTS, holiday rental in Lenox
5 STAR CASUAL ELEGANCE for 5 STAR GUESTS, holiday rental in Lenox

5 STAR CASUAL ELEGANCE for 5 STAR GUESTS

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Heart of Lenox!! - renovated downtown apartment, holiday rental in Lenox
Heart of Lenox!! - renovated downtown apartment, holiday rental in Lenox
Heart of Lenox!! - renovated downtown apartment, holiday rental in Lenox

Heart of Lenox!! - renovated downtown apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Your crisp, cool fall days are calling you...., holiday rental in Lenox
Your crisp, cool fall days are calling you...., holiday rental in Lenox
Your crisp, cool fall days are calling you...., holiday rental in Lenox

Your crisp, cool fall days are calling you....

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Enjoy comfortable elegance in this secluded grand home located in Lenox town, holiday rental in Lenox
Enjoy comfortable elegance in this secluded grand home located in Lenox town, holiday rental in Lenox
Enjoy comfortable elegance in this secluded grand home located in Lenox town, holiday rental in Lenox

Enjoy comfortable elegance in this secluded grand home located in Lenox town

Condo/Apartment
5 bedrooms
2 bathrooms
Sleeps 11
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!, holiday rental in Lenox
Heart of Lenox Walk to Town Cozy Cottage!, holiday rental in Lenox

Heart of Lenox Walk to Town Cozy Cottage!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
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, holiday rental in Lenox
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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Private, Luxury, Location1 mile to Downtown - 2.5 miles to Tanglewood, holiday rental in Lenox
Private, Luxury, Location1 mile to Downtown - 2.5 miles to Tanglewood, holiday rental in Lenox
Private, Luxury, Location1 mile to Downtown - 2.5 miles to Tanglewood, holiday rental in Lenox

Private, Luxury, Location1 mile to Downtown - 2.5 miles to Tanglewood

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Berkshires Retreat in Lenox - Main House, holiday rental in Lenox
Luxury Berkshires Retreat in Lenox - Main House, holiday rental in Lenox
Luxury Berkshires Retreat in Lenox - Main House, holiday rental in Lenox

Luxury Berkshires Retreat in Lenox - Main House

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Historical  Downtown 1bedroom, holiday rental in Lenox
Historical  Downtown 1bedroom, holiday rental in Lenox
Historical  Downtown 1bedroom, holiday rental in Lenox

Historical Downtown 1bedroom

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA, holiday rental in Lenox
Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA, holiday rental in Lenox
Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA, holiday rental in Lenox

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Restored 1881 Farm House, holiday rental in Lenox
Restored 1881 Farm House, holiday rental in Lenox
Restored 1881 Farm House, holiday rental in Lenox

Restored 1881 Farm House

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Charming, spacious country home with stunning views.....steps from Tanglewood!, holiday rental in Lenox
Charming, spacious country home with stunning views.....steps from Tanglewood!, holiday rental in Lenox
Charming, spacious country home with stunning views.....steps from Tanglewood!, holiday rental in Lenox

Charming, spacious country home with stunning views.....steps from Tanglewood!

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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The best of both worlds, Country and Culture, holiday rental in Lenox
The best of both worlds, Country and Culture, holiday rental in Lenox
The best of both worlds, Country and Culture, holiday rental in Lenox

The best of both worlds, Country and Culture

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Renovated Downtown 1bedroom, holiday rental in Lenox
Renovated Downtown 1bedroom, holiday rental in Lenox
Renovated Downtown 1bedroom, holiday rental in Lenox

Renovated Downtown 1bedroom

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEWLY RENOVATED THREE BEDROOM HAUS IN LENOX WITH MODERN INTERIOR DESIGN., holiday rental in Lenox
NEWLY RENOVATED THREE BEDROOM HAUS IN LENOX WITH MODERN INTERIOR DESIGN., holiday rental in Lenox
NEWLY RENOVATED THREE BEDROOM HAUS IN LENOX WITH MODERN INTERIOR DESIGN., holiday rental in Lenox

NEWLY RENOVATED THREE BEDROOM HAUS IN LENOX WITH MODERN INTERIOR DESIGN.

Holiday Rental House
3 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!, holiday rental in Lenox
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!, holiday rental in Lenox

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Lenox cottage within walking distance to town, holiday rental in Lenox
Charming Lenox cottage within walking distance to town, holiday rental in Lenox
Charming Lenox cottage within walking distance to town, holiday rental in Lenox

Charming Lenox cottage within walking distance to town

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Lovely Home In Heart Of Lenox  ( 1250 sq feet ), holiday rental in Lenox
Lovely Home In Heart Of Lenox  ( 1250 sq feet ), holiday rental in Lenox
Lovely Home In Heart Of Lenox  ( 1250 sq feet ), holiday rental in Lenox

Lovely Home In Heart Of Lenox ( 1250 sq feet )

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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5 Minute Dive to Tanglewood, holiday rental in Lenox
5 Minute Dive to Tanglewood, holiday rental in Lenox
5 Minute Dive to Tanglewood, holiday rental in Lenox

5 Minute Dive to Tanglewood

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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!, holiday rental in Lenox
Private Guest House in Dtwn Lenox, Walk to Dining!, holiday rental in Lenox

Private Guest House in Dtwn Lenox, Walk to Dining!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Main Street Delight 1bedroom, holiday rental in Lenox
Main Street Delight 1bedroom, holiday rental in Lenox
Main Street Delight 1bedroom, holiday rental in Lenox

Main Street Delight 1bedroom

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Staycation Lenox House -7- mins walk to downtown, holiday rental in Lenox
Staycation Lenox House -7- mins walk to downtown, holiday rental in Lenox
Staycation Lenox House -7- mins walk to downtown, holiday rental in Lenox

Staycation Lenox House -7- mins walk to downtown

Condo/Apartment
0 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
More info
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Lenox Lake House, holiday rental in Lenox
Lenox Lake House, holiday rental in Lenox
Lenox Lake House, holiday rental in Lenox

Lenox Lake House

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Come vacation in beautiful Lenox- the heart of the Berkshires!, holiday rental in Lenox
Come vacation in beautiful Lenox- the heart of the Berkshires!, holiday rental in Lenox
Come vacation in beautiful Lenox- the heart of the Berkshires!, holiday rental in Lenox

Come vacation in beautiful Lenox- the heart of the Berkshires!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Your Invited to the Berkshires!, holiday rental in Lenox
Your Invited to the Berkshires!, holiday rental in Lenox
Your Invited to the Berkshires!, holiday rental in Lenox

Your Invited to the Berkshires!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Enjoy a renovated private home right in downtown Lenox, holiday rental in Lenox
Enjoy a renovated private home right in downtown Lenox, holiday rental in Lenox
Enjoy a renovated private home right in downtown Lenox, holiday rental in Lenox

Enjoy a renovated private home right in downtown Lenox

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Historic Lenox 5 BR 5 BA renovated luxury house on 6 acres Minutes to Tanglewood, holiday rental in Lenox
Historic Lenox 5 BR 5 BA renovated luxury house on 6 acres Minutes to Tanglewood, holiday rental in Lenox
Historic Lenox 5 BR 5 BA renovated luxury house on 6 acres Minutes to Tanglewood, holiday rental in Lenox

Historic Lenox 5 BR 5 BA renovated luxury house on 6 acres Minutes to Tanglewood

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Restored Lenox Farmhouse Near Tanglewood, Including Rescued Mini Donkeys!, holiday rental in Lenox
Restored Lenox Farmhouse Near Tanglewood, Including Rescued Mini Donkeys!, holiday rental in Lenox
Restored Lenox Farmhouse Near Tanglewood, Including Rescued Mini Donkeys!, holiday rental in Lenox

Restored Lenox Farmhouse Near Tanglewood, Including Rescued Mini Donkeys!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Modern, Comfortable Classic House- Downtown Lenox, holiday rental in Lenox
Modern, Comfortable Classic House- Downtown Lenox, holiday rental in Lenox
Modern, Comfortable Classic House- Downtown Lenox, holiday rental in Lenox

Modern, Comfortable Classic House- Downtown Lenox

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Walk to Tanglewood -Luxury Dream Home - Htd Pool, Hot Tub, Stckbrdg Bowl w/Boats, holiday rental in Lenox
Walk to Tanglewood -Luxury Dream Home - Htd Pool, Hot Tub, Stckbrdg Bowl w/Boats, holiday rental in Lenox
Walk to Tanglewood -Luxury Dream Home - Htd Pool, Hot Tub, Stckbrdg Bowl w/Boats, holiday rental in Lenox

Walk to Tanglewood -Luxury Dream Home - Htd Pool, Hot Tub, Stckbrdg Bowl w/Boats

Holiday Rental House
3 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
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Heart of Lenox, holiday rental in Lenox
Heart of Lenox, holiday rental in Lenox
Heart of Lenox, holiday rental in Lenox

Heart of Lenox

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxury Berkshires Retreat in Lenox - Main House  & Studio, holiday rental in Lenox
Luxury Berkshires Retreat in Lenox - Main House  & Studio, holiday rental in Lenox
Luxury Berkshires Retreat in Lenox - Main House  & Studio, holiday rental in Lenox

Luxury Berkshires Retreat in Lenox - Main House & Studio

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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51 Church Street, Lenox MA - One Bedroom Unit, holiday rental in Lenox
51 Church Street, Lenox MA - One Bedroom Unit, holiday rental in Lenox
51 Church Street, Lenox MA - One Bedroom Unit, holiday rental in Lenox

51 Church Street, Lenox MA - One Bedroom Unit

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Sophisticated Lenox Retreat, Minutes to Downtown, holiday rental in Lenox
Sophisticated Lenox Retreat, Minutes to Downtown, holiday rental in Lenox
Sophisticated Lenox Retreat, Minutes to Downtown, holiday rental in Lenox

Sophisticated Lenox Retreat, Minutes to Downtown

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Fox Hollow Laurel Lake Ranch, holiday rental in Lenox
Fox Hollow Laurel Lake Ranch, holiday rental in Lenox
Fox Hollow Laurel Lake Ranch, holiday rental in Lenox

Fox Hollow Laurel Lake Ranch

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
More info
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Restored 1881 Farm House, holiday rental in Lenox
Restored 1881 Farm House, holiday rental in Lenox
Restored 1881 Farm House, holiday rental in Lenox

Restored 1881 Farm House

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

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
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Lenox, 1.9 Miles From Tanglewood, holiday rental in Lenox
Lenox, 1.9 Miles From Tanglewood, holiday rental in Lenox
Lenox, 1.9 Miles From Tanglewood, holiday rental in Lenox

Lenox, 1.9 Miles From Tanglewood

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Renovated 1860's Farmhouse, across from the Miraval., holiday rental in Lenox
Renovated 1860's Farmhouse, across from the Miraval., holiday rental in Lenox
Renovated 1860's Farmhouse, across from the Miraval., holiday rental in Lenox

Renovated 1860's Farmhouse, across from the Miraval.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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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, holiday rental in Lenox
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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Heart of Lenox.  Bishop Estates....Walk to Town, Tanglewood, Jacobs Pillow, holiday rental in Lenox
Heart of Lenox.  Bishop Estates....Walk to Town, Tanglewood, Jacobs Pillow, holiday rental in Lenox
Heart of Lenox.  Bishop Estates....Walk to Town, Tanglewood, Jacobs Pillow, holiday rental in Lenox

Heart of Lenox. Bishop Estates....Walk to Town, Tanglewood, Jacobs Pillow

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Renovated Lenox Haus close to downtown, holiday rental in Lenox
Renovated Lenox Haus close to downtown, holiday rental in Lenox
Renovated Lenox Haus close to downtown, holiday rental in Lenox

Renovated Lenox Haus close to downtown

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Eight Bedroom Luxury Property at Blantyre, Relais & Châteaux, holiday rental in Lenox
Eight Bedroom Luxury Property at Blantyre, Relais & Châteaux, holiday rental in Lenox
Eight Bedroom Luxury Property at Blantyre, Relais & Châteaux, holiday rental in Lenox

Eight Bedroom Luxury Property at Blantyre, Relais & Châteaux

Holiday Rental House
8 bedrooms
9 bathrooms
Sleeps 16
Match: Sleeps
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Perfect location in the heart of downtown Lenox, holiday rental in Lenox
Perfect location in the heart of downtown Lenox, holiday rental in Lenox
Perfect location in the heart of downtown Lenox, holiday rental in Lenox

Perfect location in the heart of downtown Lenox

Condo/Apartment
0 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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A walk to Tanglewood and Main Street!, holiday rental in Lenox
A walk to Tanglewood and Main Street!, holiday rental in Lenox
A walk to Tanglewood and Main Street!, holiday rental in Lenox

A walk to Tanglewood and Main Street!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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48 Main Street, Lenox MA - 48 Main Street, Lenox, MA, holiday rental in Lenox
48 Main Street, Lenox MA - 48 Main Street, Lenox, MA, holiday rental in Lenox
48 Main Street, Lenox MA - 48 Main Street, Lenox, MA, holiday rental in Lenox

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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Two Bedroom Luxury Cottage at Blantyre, Relais & Châteaux, holiday rental in Lenox
Two Bedroom Luxury Cottage at Blantyre, Relais & Châteaux, holiday rental in Lenox
Two Bedroom Luxury Cottage at Blantyre, Relais & Châteaux, holiday rental in Lenox

Two Bedroom Luxury Cottage at Blantyre, Relais & Châteaux

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Frequently Asked Questions about Lenox