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Housatonic Holiday Apartments

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50 rentals in Housatonic.
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Beautifully Renovated Colonial Home

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Spacious Contemporary With Beautiful Gardens

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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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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Downtown GB apartment walk to shops and restaurants

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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A Grand Estate in Historic Stockbridge

Holiday Rental House
6 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps
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Stockbridge! 1/2 mile from Red Lion inn. Great Barrington, Lenox, Lee close by.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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2 bedroom Riverhouse in the Heart of the Berkshires

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Vacation in a Berkshire Farmhouse

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
More info
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Great Barrington apartment, Short walk to downtown

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Stunning Renovated Victorian

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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Spectacular Housatonic River View from newly renovated Historic Cottage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Berkshire Farm House on 160+ Acres

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Renovated Colonial on the River! Fantastic Views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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A Charming Mid 1800's Stockbridge Farmhouse

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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CHARMING, Large Fireplace, VIEWS For Miles, Come RELAX

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Berkshire Farmhouse Vacation

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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COZY LOG HOME* fireplace, skiing,fall foliage Hiking, Berkshires*

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Berkshires: Romantic Cottage with spectacular view

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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CHIC UPDATED DOWNTOWN Great Barrington, Sleeps 14

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Peaceful Woodland Home in the Heart of the Berkshires

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming Housatonic Village Cape

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Excellent WiFi|Labor Day FALL Winter |The Escape at STOCKBRIDGE|The BERKSHIRES

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Monthly Discount for Ski Season Rental at Lakefront House in Great Barrington

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Rabbit Run - in the heart of Stockbridge

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Romantic Berkshires Cottage - Stunning Views, Pool

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Charming Stockbridge Historic Victorian a StoneThrow Away from the Red Lion INN

Holiday Rental House
12 bedrooms
8 bathrooms
Sleeps 24
Match: Sleeps
More info
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Case Mill-Secluded Berkshire farmhouse, mill, pond, waterfall, 28 acre forest.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Two Blocks from the Red Lion Inn & next to Berkshire Theater

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Idyllic Berkshire Get Away: Balance of relaxation and convenience

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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New to Market Renovated Home, 5 min walk to town

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Gorgeous Home, Nature Lover's Delight in the Heart of the Berkshires

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Upscale Country Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Gem of the Berkshires, walk to downtown & lake.

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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NEW LISTING SPECIAL! SAVE 10%! Impeccable House Minutes from Downtown Great Barr

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Circa 1900 Berkshire Cottage on 75 acres. Very private yet centrally located.

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Lakefront Berkshires Ski/Summer House, Great Views

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Newly Renovated Colonial on the River! Sleeps 5-6

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Stockbridge renovated classic- picture perfect

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful house on 'The Hill' just minutes from Lake Mansfield and Town.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Eco-friendly cozy home in Gt. Barrington

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Renovated house on the Hill. Walk everywhere!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Iris Room

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Horse Room

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Renovated family friendly house close to everything and endless views

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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'Too Good' AKA 2 Goodrich St.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Luxurious modern estate w/ heated pool, hot tub, and lakefront!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
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Farmhouse from a magazine

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Dream Land 10 min from town

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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