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Holiday Rentals in Lenox

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
67 rentals in Lenox.
NEW! Lenox Home Mins to Tanglewood Shakespeare & Co, holiday rental in Lenox
NEW! Lenox Home Mins to Tanglewood Shakespeare & Co, holiday rental in Lenox
NEW! Lenox Home Mins to Tanglewood Shakespeare & Co, holiday rental in Lenox

NEW! Lenox Home Mins to Tanglewood Shakespeare & Co

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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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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 6
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!, 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
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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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
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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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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
More info
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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 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, 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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Cozy Condo, walk to town, private and bright, holiday rental in Lenox
Cozy Condo, walk to town, private and bright, holiday rental in Lenox
Cozy Condo, walk to town, private and bright, holiday rental in Lenox

Cozy Condo, walk to town, private and bright

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Private Apartment in the Heart of Downtown Lenox, holiday rental in Lenox
Private Apartment in the Heart of Downtown Lenox, holiday rental in Lenox
Private Apartment in the Heart of Downtown Lenox, holiday rental in Lenox

Private Apartment in the Heart of Downtown Lenox

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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One Bedroom Luxury Cottage at Blantyre, Relais & Châteaux, holiday rental in Lenox
One Bedroom Luxury Cottage at Blantyre, Relais & Châteaux, holiday rental in Lenox
One Bedroom Luxury Cottage at Blantyre, Relais & Châteaux, holiday rental in Lenox

One Bedroom Luxury Cottage at Blantyre, Relais & Châteaux

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Condo with Resort Amenities in Lenox, holiday rental in Lenox
Condo with Resort Amenities in Lenox, holiday rental in Lenox
Condo with Resort Amenities in Lenox, holiday rental in Lenox

Condo with Resort Amenities in Lenox

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Beautiful Berkshires Historic Lenox Home, holiday rental in Lenox
Beautiful Berkshires Historic Lenox Home, holiday rental in Lenox
Beautiful Berkshires Historic Lenox Home, holiday rental in Lenox

Beautiful Berkshires Historic Lenox Home

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Walk to Town, holiday rental in Lenox
Walk to Town, holiday rental in Lenox
Walk to Town, holiday rental in Lenox

Walk to Town

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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BERKSHIRES CHARM! Lenox, Tanglewood!  SUMMER ONLY, or LongTerm Rental. Location!, holiday rental in Lenox
BERKSHIRES CHARM! Lenox, Tanglewood!  SUMMER ONLY, or LongTerm Rental. Location!, holiday rental in Lenox
BERKSHIRES CHARM! Lenox, Tanglewood!  SUMMER ONLY, or LongTerm Rental. Location!, holiday rental in Lenox

BERKSHIRES CHARM! Lenox, Tanglewood! SUMMER ONLY, or LongTerm Rental. Location!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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
More info
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Renovated 1 bedroom in the city center, holiday rental in Lenox
Renovated 1 bedroom in the city center, holiday rental in Lenox
Renovated 1 bedroom in the city center, holiday rental in Lenox

Renovated 1 bedroom in the city center

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Long term vacation rental. Quiet clean and comfortable all one level, holiday rental in Lenox
Long term vacation rental. Quiet clean and comfortable all one level, holiday rental in Lenox
Long term vacation rental. Quiet clean and comfortable all one level, holiday rental in Lenox

Long term vacation rental. Quiet clean and comfortable all one level

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!, holiday rental in Lenox
Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!, holiday rental in Lenox
Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!, holiday rental in Lenox

Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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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
More info
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Historic Lenox Village Summer Rental, holiday rental in Lenox
Historic Lenox Village Summer Rental, holiday rental in Lenox
Historic Lenox Village Summer Rental, holiday rental in Lenox

Historic Lenox Village Summer Rental

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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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
1 bathroom
Sleeps 4
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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Family fun * The Ponds at Foxhollow Resort, holiday rental in Lenox
Family fun * The Ponds at Foxhollow Resort, holiday rental in Lenox
Family fun * The Ponds at Foxhollow Resort, holiday rental in Lenox

Family fun * The Ponds at Foxhollow Resort

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Check-out
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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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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 6
Match: Sleeps
More info
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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
More info
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Cozy Condo with resort amenities, holiday rental in Lenox
Cozy Condo with resort amenities, holiday rental in Lenox
Cozy Condo with resort amenities, holiday rental in Lenox

Cozy Condo with resort amenities

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Center of Lenox, cozy Apartment 2-bedroomREVIEWS, holiday rental in Lenox
Center of Lenox, cozy Apartment 2-bedroomREVIEWS, holiday rental in Lenox
Center of Lenox, cozy Apartment 2-bedroomREVIEWS, holiday rental in Lenox

Center of Lenox, cozy Apartment 2-bedroomREVIEWS

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Center of Lenox, cozy 2-bedroom apartment REVIEWS, holiday rental in Lenox
Center of Lenox, cozy 2-bedroom apartment REVIEWS, holiday rental in Lenox
Center of Lenox, cozy 2-bedroom apartment REVIEWS, holiday rental in Lenox

Center of Lenox, cozy 2-bedroom apartment REVIEWS

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Lenox House w/ Screened Patio & Mountain View, holiday rental in Lenox
Lenox House w/ Screened Patio & Mountain View, holiday rental in Lenox
Lenox House w/ Screened Patio & Mountain View, holiday rental in Lenox

Lenox House w/ Screened Patio & Mountain View

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Lenox - Walk to Town - Berkshire Home, holiday rental in Lenox
Lenox - Walk to Town - Berkshire Home, holiday rental in Lenox
Lenox - Walk to Town - Berkshire Home, holiday rental in Lenox

Lenox - Walk to Town - Berkshire Home

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Enveloped in Nature * Lenox, holiday rental in Lenox
Enveloped in Nature * Lenox, holiday rental in Lenox
Enveloped in Nature * Lenox, holiday rental in Lenox

Enveloped in Nature * Lenox

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Lovely Townhouse In Heart Of Lenox, holiday rental in Lenox
Lovely Townhouse In Heart Of Lenox, holiday rental in Lenox
Lovely Townhouse In Heart Of Lenox, holiday rental in Lenox

Lovely Townhouse In Heart Of Lenox

Holiday Rental House
2 bedrooms
2 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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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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Payment Protection
Steps away from shops and restaurants of Lenox Village, with private forest, holiday rental in Lenox
Steps away from shops and restaurants of Lenox Village, with private forest, holiday rental in Lenox
Steps away from shops and restaurants of Lenox Village, with private forest, holiday rental in Lenox

Steps away from shops and restaurants of Lenox Village, with private forest

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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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Family friendly house with two complete units, private deck and yard., holiday rental in Lenox
Family friendly house with two complete units, private deck and yard., holiday rental in Lenox
Family friendly house with two complete units, private deck and yard., holiday rental in Lenox

Family friendly house with two complete units, private deck and yard.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Mid-Century Modern Berkshires Getaway on 6.5 Acres!, holiday rental in Lenox
Mid-Century Modern Berkshires Getaway on 6.5 Acres!, holiday rental in Lenox
Mid-Century Modern Berkshires Getaway on 6.5 Acres!, holiday rental in Lenox

Mid-Century Modern Berkshires Getaway on 6.5 Acres!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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
More info
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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
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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Huge Designer House on 2 acres property, minutes to restaurants, museums, holiday rental in Lenox
Huge Designer House on 2 acres property, minutes to restaurants, museums, holiday rental in Lenox
Huge Designer House on 2 acres property, minutes to restaurants, museums, holiday rental in Lenox

Huge Designer House on 2 acres property, minutes to restaurants, museums

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Penthouse, Downtown Lenox, holiday rental in Lenox
The Penthouse, Downtown Lenox, holiday rental in Lenox
The Penthouse, Downtown Lenox, holiday rental in Lenox

The Penthouse, Downtown Lenox

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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New! Inspired Country Retreat in Lenox Sleeps 8, holiday rental in Lenox
New! Inspired Country Retreat in Lenox Sleeps 8, holiday rental in Lenox
New! Inspired Country Retreat in Lenox Sleeps 8, holiday rental in Lenox

New! Inspired Country Retreat in Lenox Sleeps 8

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Showing results 1-50 of 67
Frequently Asked Questions about Lenox