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Old Chatham Vacation Rentals

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51 rentals in Old Chatham.
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Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!, vacation rental in Old Chatham

Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Secluded House with Picturesque Views in Historic Old Chatham, NY, vacation rental in Old Chatham

Secluded House with Picturesque Views in Historic Old Chatham, NY

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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nesteldown pet friendly, vacation rental in Old Chatham

nesteldown pet friendly

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beauty in the Berkshires, vacation rental in Old Chatham

Beauty in the Berkshires

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Recently renovated 4 bedroom lakefront house in The Berkshires., vacation rental in Old Chatham

Recently renovated 4 bedroom lakefront house in The Berkshires.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Newly Renovated 1910 Farmhouse - Walk To Town - Perfect Berkshire Retreat, vacation rental in Old Chatham

Newly Renovated 1910 Farmhouse - Walk To Town - Perfect Berkshire Retreat

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Vacation in a  Berkshire Farmhouse, vacation rental in Old Chatham

Vacation in a Berkshire Farmhouse

5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Tranquil Lake House Getaway on Onota Lake, vacation rental in Old Chatham

Tranquil Lake House Getaway on Onota Lake

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Heaven Cant Wait, On Beautiful Kinderhook, vacation rental in Old Chatham

Heaven Cant Wait, On Beautiful Kinderhook

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming, Quiet, Modern, Wooded, River Front, vacation rental in Old Chatham

Charming, Quiet, Modern, Wooded, River Front

3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Berkshire Farmhouse Vacation, vacation rental in Old Chatham

Berkshire Farmhouse Vacation

5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Designer Home with Panoramic Views near Hudson, vacation rental in Old Chatham

Designer Home with Panoramic Views near Hudson

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b, vacation rental in Old Chatham

Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Charming Farmhouse Steps from Downtown West Stockbridge, vacation rental in Old Chatham

Charming Farmhouse Steps from Downtown West Stockbridge

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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CLOSE TO SKIING /HOT TUB /FIBER OPTIC WIFI/ 1NIGHT CANYON RANCH CHEF AVAILABLE, vacation rental in Old Chatham

CLOSE TO SKIING /HOT TUB /FIBER OPTIC WIFI/ 1NIGHT CANYON RANCH CHEF AVAILABLE

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Quiet Guest House In The Green River Valley, vacation rental in Old Chatham

Quiet Guest House In The Green River Valley

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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A Beautiful Retreat In a Stunning Home and Landscaped Lawns, vacation rental in Old Chatham

A Beautiful Retreat In a Stunning Home and Landscaped Lawns

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Heavenly Kinderhook Lake!, vacation rental in Old Chatham

Heavenly Kinderhook Lake!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Home in Malden Bridge, Columbia County, New York, vacation rental in Old Chatham

The Home in Malden Bridge, Columbia County, New York

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Modern Retreat with Stunning Western Views, vacation rental in Old Chatham

Modern Retreat with Stunning Western Views

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cabin on forest road, vacation rental in Old Chatham

Cabin on forest road

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Historical Dutch Gem In The Hudson Valley, vacation rental in Old Chatham

Historical Dutch Gem In The Hudson Valley

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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SPECTACULAR RENOVATED BERKSHIRE LAKEFRONT HOUSE ON RICHMOND POND, vacation rental in Old Chatham

SPECTACULAR RENOVATED BERKSHIRE LAKEFRONT HOUSE ON RICHMOND POND

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Carriage House Charmer, vacation rental in Old Chatham

Carriage House Charmer

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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BERKSHIRES-3BR2BA now-9/9  &/or  11/1-WINTER/SPRING RENT - NR JIMINY PK, vacation rental in Old Chatham

BERKSHIRES-3BR2BA now-9/9 &/or 11/1-WINTER/SPRING RENT - NR JIMINY PK

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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A MAGIC SPOT: Booking Fall and the Ski Season now!, vacation rental in Old Chatham

A MAGIC SPOT: Booking Fall and the Ski Season now!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private Hillsdale Home With Views Of Catamount., vacation rental in Old Chatham

Private Hillsdale Home With Views Of Catamount.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Welcome to WIndswept Acres in the Berkshire Mts!, vacation rental in Old Chatham

Welcome to WIndswept Acres in the Berkshire Mts!

3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sophisticated &  Comfortable Stockbridge Retreat  A+ Location  Modern Amenities, vacation rental in Old Chatham

Sophisticated & Comfortable Stockbridge Retreat A+ Location Modern Amenities

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Morning Face - Berkshire estate with heated pool, views and privacy., vacation rental in Old Chatham

Morning Face - Berkshire estate with heated pool, views and privacy.

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Long term availability Berkshire chalet with hot tub and fast WIFI, vacation rental in Old Chatham

Long term availability Berkshire chalet with hot tub and fast WIFI

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hudson River Beach House, vacation rental in Old Chatham

Hudson River Beach House

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Relax in the Country - Peace, quiet and family friendly, vacation rental in Old Chatham

Relax in the Country - Peace, quiet and family friendly

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning New Construction All SeasonLakefront Home, vacation rental in Old Chatham

Stunning New Construction All SeasonLakefront Home

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Cozy apartment overlooking our small farm.  Family Friendly., vacation rental in Old Chatham

Cozy apartment overlooking our small farm. Family Friendly.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Secluded Family-Friendly Home, vacation rental in Old Chatham

Secluded Family-Friendly Home

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hillhouse Log Cabin, vacation rental in Old Chatham

Hillhouse Log Cabin

3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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The Meadow House 4 bdrm 4 bath house, vacation rental in Old Chatham

The Meadow House 4 bdrm 4 bath house

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Roaring Rapids Cottage, vacation rental in Old Chatham

Roaring Rapids Cottage

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Total Privacy! Tanglewood Retreat With Berkshire Views!, vacation rental in Old Chatham

Total Privacy! Tanglewood Retreat With Berkshire Views!

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Modern Cozy Wooded Retreat, vacation rental in Old Chatham

Modern Cozy Wooded Retreat

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Leisure home with beach front property, vacation rental in Old Chatham

Leisure home with beach front property

6 bedrooms
3 bathrooms
Sleeps 25
Match: Sleeps
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Historic Gem Near Hudson, NY, vacation rental in Old Chatham

Historic Gem Near Hudson, NY

1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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WE'RE SHUTTING DOWN FOR THE PANDEMIC.  STAY SAFE AND WELL, vacation rental in Old Chatham

WE'RE SHUTTING DOWN FOR THE PANDEMIC. STAY SAFE AND WELL

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Tentrr Signature Site - Berkshire Mountain Hideaway, vacation rental in Old Chatham

Tentrr Signature Site - Berkshire Mountain Hideaway

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Round Mountain Camp, vacation rental in Old Chatham

Tentrr Signature Site - Round Mountain Camp

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Hudson Valley Berkshires Cottage, vacation rental in Old Chatham

Hudson Valley Berkshires Cottage

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Chalet near 4 ski resorts with hot tub, vacation rental in Old Chatham

Chalet near 4 ski resorts with hot tub

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious secluded  yet close to everything, vacation rental in Old Chatham

Spacious secluded yet close to everything

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - WATER + WOODS, vacation rental in Old Chatham

Tentrr Signature Site - WATER + WOODS

1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
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