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South Lee Holiday Apartments

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50 rentals in South Lee.
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Villa with Access to 2 Pools, a Hot Tub, an 18-Hole Mini Golf Course, and More, holiday rental in South Lee
Villa with Access to 2 Pools, a Hot Tub, an 18-Hole Mini Golf Course, and More, holiday rental in South Lee
Villa with Access to 2 Pools, a Hot Tub, an 18-Hole Mini Golf Course, and More, holiday rental in South Lee

Villa with Access to 2 Pools, a Hot Tub, an 18-Hole Mini Golf Course, and More

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beartown Forest Farmhouse -- 4 Minutes To Downtown Stockbridge, holiday rental in South Lee
Beartown Forest Farmhouse -- 4 Minutes To Downtown Stockbridge, holiday rental in South Lee
Beartown Forest Farmhouse -- 4 Minutes To Downtown Stockbridge, holiday rental in South Lee

Beartown Forest Farmhouse -- 4 Minutes To Downtown Stockbridge

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!, holiday rental in South Lee
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!, holiday rental in South Lee
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!, holiday rental in South Lee

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Spring Break Special!  Stay two nights get one free for March and April!, holiday rental in South Lee
Spring Break Special!  Stay two nights get one free for March and April!, holiday rental in South Lee
Spring Break Special!  Stay two nights get one free for March and April!, holiday rental in South Lee

Spring Break Special! Stay two nights get one free for March and April!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lovingly restored Victorian in Lee's Historic District **Spring:3rd nt 1/2 off, holiday rental in South Lee
Lovingly restored Victorian in Lee's Historic District **Spring:3rd nt 1/2 off, holiday rental in South Lee
Lovingly restored Victorian in Lee's Historic District **Spring:3rd nt 1/2 off, holiday rental in South Lee

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

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Modern And Spacious Berkshires Retreat 5 bdrm 3 bath, holiday rental in South Lee
Modern And Spacious Berkshires Retreat 5 bdrm 3 bath, holiday rental in South Lee
Modern And Spacious Berkshires Retreat 5 bdrm 3 bath, holiday rental in South Lee

Modern And Spacious Berkshires Retreat 5 bdrm 3 bath

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Elegant 19th Century New England 2BR Vacation Rental at Garfield House, holiday rental in South Lee
Elegant 19th Century New England 2BR Vacation Rental at Garfield House, holiday rental in South Lee
Elegant 19th Century New England 2BR Vacation Rental at Garfield House, holiday rental in South Lee

Elegant 19th Century New England 2BR Vacation Rental at Garfield House

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A Grand Estate in Historic Stockbridge, holiday rental in South Lee
A Grand Estate in Historic Stockbridge, holiday rental in South Lee
A Grand Estate in Historic Stockbridge, holiday rental in South Lee

A Grand Estate in Historic Stockbridge

Holiday Rental House
6 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps
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General Williams Estate House Lenox/Stockbridge, holiday rental in South Lee
General Williams Estate House Lenox/Stockbridge, holiday rental in South Lee
General Williams Estate House Lenox/Stockbridge, holiday rental in South Lee

General Williams Estate House Lenox/Stockbridge

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Spectacular Housatonic River View from newly renovated Historic Cottage, holiday rental in South Lee
Spectacular Housatonic River View from newly renovated Historic Cottage, holiday rental in South Lee
Spectacular Housatonic River View from newly renovated Historic Cottage, holiday rental in South Lee

Spectacular Housatonic River View from newly renovated Historic Cottage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Gorgeous, Private, Family-Friendly, Organic Home with a Great Location in Lee, holiday rental in South Lee
Gorgeous, Private, Family-Friendly, Organic Home with a Great Location in Lee, holiday rental in South Lee
Gorgeous, Private, Family-Friendly, Organic Home with a Great Location in Lee, holiday rental in South Lee

Gorgeous, Private, Family-Friendly, Organic Home with a Great Location in Lee

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A Charming Mid 1800's Stockbridge Farmhouse, holiday rental in South Lee
A Charming Mid 1800's Stockbridge Farmhouse, holiday rental in South Lee
A Charming Mid 1800's Stockbridge Farmhouse, holiday rental in South Lee

A Charming Mid 1800's Stockbridge Farmhouse

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming 1860 Farmhouse, Completely Renovated, Convenient Location, Central AC, holiday rental in South Lee
Charming 1860 Farmhouse, Completely Renovated, Convenient Location, Central AC, holiday rental in South Lee
Charming 1860 Farmhouse, Completely Renovated, Convenient Location, Central AC, holiday rental in South Lee

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Newly renovated 1500 sqft private entrance with beautiful views!, holiday rental in South Lee
Newly renovated 1500 sqft private entrance with beautiful views!, holiday rental in South Lee
Newly renovated 1500 sqft private entrance with beautiful views!, holiday rental in South Lee

Newly renovated 1500 sqft private entrance with beautiful views!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Elegant 19th Century New England Newly Renovated 1BR Vacation Rental, holiday rental in South Lee
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental, holiday rental in South Lee
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental, holiday rental in South Lee

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

Condo/Apartment
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 South Lee
2 Bedroom newly renovated townehouse, beautifully decorated at Garfield House, holiday rental in South Lee
2 Bedroom newly renovated townehouse, beautifully decorated at Garfield House, holiday rental in South Lee

2 Bedroom newly renovated townehouse, beautifully decorated at Garfield House

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Rabbit Run - 5 minute walk to Stockbridge Village, holiday rental in South Lee
Rabbit Run - 5 minute walk to Stockbridge Village, holiday rental in South Lee
Rabbit Run - 5 minute walk to Stockbridge Village, holiday rental in South Lee

Rabbit Run - 5 minute walk to Stockbridge Village

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Garfield House Studio at 208, holiday rental in South Lee
Garfield House Studio at 208, holiday rental in South Lee
Garfield House Studio at 208, holiday rental in South Lee

Garfield House Studio at 208

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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In the Heart of Everything, holiday rental in South Lee
In the Heart of Everything, holiday rental in South Lee
In the Heart of Everything, holiday rental in South Lee

In the Heart of Everything

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Two Blocks from the Red Lion Inn & next to Berkshire Theater, holiday rental in South Lee
Two Blocks from the Red Lion Inn & next to Berkshire Theater, holiday rental in South Lee
Two Blocks from the Red Lion Inn & next to Berkshire Theater, holiday rental in South Lee

Two Blocks from the Red Lion Inn & next to Berkshire Theater

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Holiday in Norman Rockwell's Stockbridge, holiday rental in South Lee
Holiday in Norman Rockwell's Stockbridge, holiday rental in South Lee
Holiday in Norman Rockwell's Stockbridge, holiday rental in South Lee

Holiday in Norman Rockwell's Stockbridge

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Expansive Berkshires walk to town, holiday rental in South Lee
Expansive Berkshires walk to town, holiday rental in South Lee
Expansive Berkshires walk to town, holiday rental in South Lee

Expansive Berkshires walk to town

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Upscale Architecturally Designed Berkshire Home, holiday rental in South Lee
Upscale Architecturally Designed Berkshire Home, holiday rental in South Lee
Upscale Architecturally Designed Berkshire Home, holiday rental in South Lee

Upscale Architecturally Designed Berkshire Home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Fox Hollow Lakeside Condo, Minutes to Tanglewood, holiday rental in South Lee
Fox Hollow Lakeside Condo, Minutes to Tanglewood, holiday rental in South Lee
Fox Hollow Lakeside Condo, Minutes to Tanglewood, holiday rental in South Lee

Fox Hollow Lakeside Condo, Minutes to Tanglewood

Condo/Apartment
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Circa 1900 Berkshire Cottage on 75 acres.  Very private yet centrally located., holiday rental in South Lee
Circa 1900 Berkshire Cottage on 75 acres.  Very private yet centrally located., holiday rental in South Lee
Circa 1900 Berkshire Cottage on 75 acres.  Very private yet centrally located., holiday rental in South Lee

Circa 1900 Berkshire Cottage on 75 acres. Very private yet centrally located.

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Stockbridge renovated classic- picture perfect, holiday rental in South Lee
Stockbridge renovated classic- picture perfect, holiday rental in South Lee
Stockbridge renovated classic- picture perfect, holiday rental in South Lee

Stockbridge renovated classic- picture perfect

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Charming Home w/ Yard - Walk to Laurel Lake!, holiday rental in South Lee
NEW! Charming Home w/ Yard - Walk to Laurel Lake!, holiday rental in South Lee
NEW! Charming Home w/ Yard - Walk to Laurel Lake!, holiday rental in South Lee

NEW! Charming Home w/ Yard - Walk to Laurel Lake!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Fox Hollow Laurel Lake Ranch, holiday rental in South Lee
Fox Hollow Laurel Lake Ranch, holiday rental in South Lee
Fox Hollow Laurel Lake Ranch, holiday rental in South Lee

Fox Hollow Laurel Lake Ranch

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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Garfield House, holiday rental in South Lee
Garfield House, holiday rental in South Lee
Garfield House, holiday rental in South Lee

Garfield House

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE, holiday rental in South Lee
LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE, holiday rental in South Lee
LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE, holiday rental in South Lee

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Vacation Home on 10 Acres with Pool and Spa, holiday rental in South Lee
Vacation Home on 10 Acres with Pool and Spa, holiday rental in South Lee
Vacation Home on 10 Acres with Pool and Spa, holiday rental in South Lee

Vacation Home on 10 Acres with Pool and Spa

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Home with Pool on 10 Acres, holiday rental in South Lee
Home with Pool on 10 Acres, holiday rental in South Lee
Home with Pool on 10 Acres, holiday rental in South Lee

Home with Pool on 10 Acres

Holiday Rental House
3 bedrooms
2 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 South Lee
Beautiful, secluded, private resort in the heart of the Berkshires in Lenox, MA, holiday rental in South Lee
Beautiful, secluded, private resort in the heart of the Berkshires in Lenox, MA, holiday rental in South Lee

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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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"Too Good" AKA 2 Goodrich St., holiday rental in South Lee
"Too Good" AKA 2 Goodrich St., holiday rental in South Lee
"Too Good" AKA 2 Goodrich St., holiday rental in South Lee

"Too Good" AKA 2 Goodrich St.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Stockbridge Estate with Mountain Views, holiday rental in South Lee
Stockbridge Estate with Mountain Views, holiday rental in South Lee
Stockbridge Estate with Mountain Views, holiday rental in South Lee

Stockbridge Estate with Mountain Views

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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** Private Berkshire Escape** Monthly Pricing Available, holiday rental in South Lee
** Private Berkshire Escape** Monthly Pricing Available, holiday rental in South Lee
** Private Berkshire Escape** Monthly Pricing Available, holiday rental in South Lee

** Private Berkshire Escape** Monthly Pricing Available

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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One block from Main St Stockbridge, holiday rental in South Lee
One block from Main St Stockbridge, holiday rental in South Lee
One block from Main St Stockbridge, holiday rental in South Lee

One block from Main St Stockbridge

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Berkshire Get away, holiday rental in South Lee
Berkshire Get away, holiday rental in South Lee
Berkshire Get away, holiday rental in South Lee

Berkshire Get away

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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2 Bedroom/2 Bath Luxury Condo in the Berkshires, holiday rental in South Lee
2 Bedroom/2 Bath Luxury Condo in the Berkshires, holiday rental in South Lee
2 Bedroom/2 Bath Luxury Condo in the Berkshires, holiday rental in South Lee

2 Bedroom/2 Bath Luxury Condo in the Berkshires

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy Berkshire Retreat, Just Near the Laurel Lake!, holiday rental in South Lee
Cozy Berkshire Retreat, Just Near the Laurel Lake!, holiday rental in South Lee
Cozy Berkshire Retreat, Just Near the Laurel Lake!, holiday rental in South Lee

Cozy Berkshire Retreat, Just Near the Laurel Lake!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mountain Views In Lee,Centrally Located, Book Now!, holiday rental in South Lee
Mountain Views In Lee,Centrally Located, Book Now!, holiday rental in South Lee
Mountain Views In Lee,Centrally Located, Book Now!, holiday rental in South Lee

Mountain Views In Lee,Centrally Located, Book Now!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Historic Stockbridge Villa on 25 acres sleeps 23, holiday rental in South Lee
Historic Stockbridge Villa on 25 acres sleeps 23, holiday rental in South Lee
Historic Stockbridge Villa on 25 acres sleeps 23, holiday rental in South Lee

Historic Stockbridge Villa on 25 acres sleeps 23

Holiday Rental House
12 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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Fox Hollow Luxury Ranch Laurel Lake, holiday rental in South Lee
Fox Hollow Luxury Ranch Laurel Lake, holiday rental in South Lee
Fox Hollow Luxury Ranch Laurel Lake, holiday rental in South Lee

Fox Hollow Luxury Ranch Laurel Lake

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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Stockbridge -Walk to Town & Steps to Hiking Trail, too!, holiday rental in South Lee
Stockbridge -Walk to Town & Steps to Hiking Trail, too!, holiday rental in South Lee
Stockbridge -Walk to Town & Steps to Hiking Trail, too!, holiday rental in South Lee

Stockbridge -Walk to Town & Steps to Hiking Trail, too!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Stylish Mid-century Modern Berkshires Cape, holiday rental in South Lee
Stylish Mid-century Modern Berkshires Cape, holiday rental in South Lee
Stylish Mid-century Modern Berkshires Cape, holiday rental in South Lee

Stylish Mid-century Modern Berkshires Cape

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Perfect New England-y Condo Resort, Berkshire, holiday rental in South Lee
Perfect New England-y Condo Resort, Berkshire, holiday rental in South Lee
Perfect New England-y Condo Resort, Berkshire, holiday rental in South Lee

Perfect New England-y Condo Resort, Berkshire

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Great house in Stockbridge, holiday rental in South Lee
Great house in Stockbridge, holiday rental in South Lee
Great house in Stockbridge, holiday rental in South Lee

Great house in Stockbridge

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Home in AMAZING Berkshire Location, holiday rental in South Lee
Beautiful Home in AMAZING Berkshire Location, holiday rental in South Lee
Beautiful Home in AMAZING Berkshire Location, holiday rental in South Lee

Beautiful Home in AMAZING Berkshire Location

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Serenity Now in the Berkshires!One Month Discount!, holiday rental in South Lee
Serenity Now in the Berkshires!One Month Discount!, holiday rental in South Lee
Serenity Now in the Berkshires!One Month Discount!, holiday rental in South Lee

Serenity Now in the Berkshires!One Month Discount!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Rooms on the River/Berkshire Retreat, holiday rental in South Lee
Rooms on the River/Berkshire Retreat, holiday rental in South Lee
Rooms on the River/Berkshire Retreat, holiday rental in South Lee

Rooms on the River/Berkshire Retreat

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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