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Holiday Rentals in Old Chatham

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51 rentals in Old Chatham.
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Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!
2 bedrooms
1 bathroom
Sleeps 6
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Bellavista Country Estate - The Library Suite
2 bedrooms
1 bathroom
Sleeps 4
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nesteldown pet friendly
4 bedrooms
3 bathrooms
Sleeps 8
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Beautiful Bellavista Country Estate
8 bedrooms
5 bathrooms
Sleeps 16
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Bellavista Country Estate - Rose Suite
2 bedrooms
1 bathroom
Sleeps 4
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Secluded House with Picturesque Views in Historic Old Chatham, NY
4 bedrooms
4 bathrooms
Sleeps 8
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Beauty in the Berkshires
7 bedrooms
5 bathrooms
Sleeps 16
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Recently renovated 4 bedroom lakefront house in The Berkshires.
4 bedrooms
3 bathrooms
Sleeps 8
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4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town.
4 bedrooms
2 bathrooms
Sleeps 10
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Private Romantic Cottage on a 7 Acre Estate- Swimming Pond, Gardens, View
1 bedroom
1 bathroom
Sleeps 2
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Heaven Cant Wait, On Beautiful Kinderhook
2 bedrooms
1 bathroom
Sleeps 6
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WE'RE SHUTTING DOWN FOR THE PANDEMIC. STAY SAFE AND WELL
4 bedrooms
4 bathrooms
Sleeps 12
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Designer Home with Panoramic Views near Hudson
4 bedrooms
3 bathrooms
Sleeps 7
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Charming Farmhouse Steps from Downtown West Stockbridge
2 bedrooms
2 bathrooms
Sleeps 5
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CLOSE TO SKIING /HOT TUB /FIBER OPTIC WIFI/ 1NIGHT CANYON RANCH CHEF AVAILABLE
3 bedrooms
4 bathrooms
Sleeps 10
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Beautiful 3 BR Berkshire Home - Mountain Views & Privacy on 10 Acres
3 bedrooms
3 bathrooms
Sleeps 6
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Cabin on forest road
1 bedroom
1 bathroom
Sleeps 2
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SPECTACULAR RENOVATED BERKSHIRE LAKEFRONT HOUSE ON RICHMOND POND
3 bedrooms
3 bathrooms
Sleeps 6
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Carriage House Charmer
2 bedrooms
1 bathroom
Sleeps 4
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'Fall' in love with the Berkshire or 'Winter in !!!
3 bedrooms
3 bathrooms
Sleeps 8
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14 other travellers have booked this property
Historical Dutch Gem In The Hudson Valley
4 bedrooms
2 bathrooms
Sleeps 10
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Welcome to WIndswept Acres in the Berkshire Mts!
3 bedrooms
1 bathroom
Sleeps 4
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Berkshire Blueberry Lodge LLC - Near Jiminy Peak
4 bedrooms
2 bathrooms
Sleeps 10
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Long term availability Berkshire chalet with hot tub and fast WIFI
4 bedrooms
3 bathrooms
Sleeps 8
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Modern Retreat with Stunning Western Views
2 bedrooms
2 bathrooms
Sleeps 4
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Relax in the Country - Peace, quiet and family friendly
3 bedrooms
2 bathrooms
Sleeps 8
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Stunning New Construction All SeasonLakefront Home
3 bedrooms
3 bathrooms
Sleeps 5
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Cozy apartment overlooking our small farm. Family Friendly.
2 bedrooms
1 bathroom
Sleeps 6
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Morning Face - Berkshire estate with heated pool, views and privacy.
4 bedrooms
5 bathrooms
Sleeps 10
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Secluded Family-Friendly Home
3 bedrooms
3 bathrooms
Sleeps 8
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Pineview - Ideal Escape
6 bedrooms
4 bathrooms
Sleeps 14
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The Home in Malden Bridge, Columbia County, New York
2 bedrooms
3 bathrooms
Sleeps 4
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The Meadow House 4 bdrm 4 bath house
4 bedrooms
4 bathrooms
Sleeps 12
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1 other traveller has booked this property
The Dacha: Summer/Skiing House in the Berkshires
2 bedrooms
2 bathrooms
Sleeps 6
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Cedar Chest
1 bedroom
1 bathroom
Sleeps 2
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Modern Cozy Wooded Retreat
2 bedrooms
2 bathrooms
Sleeps 6
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Country estate on 100 acres perfect for families
4 bedrooms
4 bathrooms
Sleeps 6
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Historic Gem Near Hudson, NY
1 bedroom
2 bathrooms
Sleeps 3
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1 other traveller has booked this property
Brook Hill Farm House
4 bedrooms
3 bathrooms
Sleeps 12
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1 other traveller has booked this property
Red Mapple Farm
4 bedrooms
2 bathrooms
Sleeps 8
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Lakefront Averill Park Home w/Patio, Fire Pit
1 bedroom
1 bathroom
Sleeps 4
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Tentrr Signature Site - Berkshire Mountain Hideaway
1 bedroom
1 bathroom
Sleeps 4
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Hudson Valley Berkshires Cottage
2 bedrooms
2 bathrooms
Sleeps 4
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A Beautiful Retreat In a Stunning Home and Landscaped Lawns
5 bedrooms
4 bathrooms
Sleeps 10
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Chalet near 4 ski resorts with hot tub
3 bedrooms
3 bathrooms
Sleeps 8
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Spacious secluded yet close to everything
3 bedrooms
2 bathrooms
Sleeps 6
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Winter Wonderland, minutes to Hudson and Berkshires
1 bedroom
1 bathroom
Sleeps 2
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Tentrr Signature Site - WATER + WOODS
1 bedroom
1 bathroom
Sleeps 10
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Tentrr Signature Site - The Lodge's Campsite
1 bedroom
1 bathroom
Sleeps 6
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A MAGIC SPOT: Booking Fall and the Ski Season now!
4 bedrooms
2 bathrooms
Sleeps 8
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