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Chatham Vacation Rentals

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50 rentals in Chatham.
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CLOSE TO SKIING /HOT TUB /FIBER OPTIC WIFI/ 1NIGHT CANYON RANCH CHEF AVAILABLE, vacation rental in Chatham

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

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Relax in the Country - Peace, quiet and family friendly, vacation rental in Chatham

Relax in the Country - Peace, quiet and family friendly

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

Beauty in the Berkshires

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Secluded and Private Location in the Mountains yet close to Skiing & attractions, vacation rental in Chatham

Secluded and Private Location in the Mountains yet close to Skiing & attractions

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Berkshire Farmhouse Vacation, vacation rental in Chatham

Berkshire Farmhouse Vacation

5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Vacation in a  Berkshire Farmhouse, vacation rental in Chatham

Vacation in a Berkshire Farmhouse

5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Newly Renovated 1910 Farmhouse - Walk To Town - Perfect Berkshire Retreat, vacation rental in Chatham

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

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Farm House on beautiful old Horse Farm!!, vacation rental in Chatham

Farm House on beautiful old Horse Farm!!

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town., vacation rental in Chatham

4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town.

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

Charming, Quiet, Modern, Wooded, River Front

3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Designer Home with Panoramic Views near Hudson, vacation rental in Chatham

Designer Home with Panoramic Views near Hudson

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

Charming Farmhouse Steps from Downtown West Stockbridge

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Escape to Hudson NY!, vacation rental in Chatham

Escape to Hudson NY!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!, vacation rental in Chatham

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Light-Filled Hudson Home with Designer Sauna & Swimming Pool, vacation rental in Chatham

Light-Filled Hudson Home with Designer Sauna & Swimming Pool

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Quiet Guest House In The Green River Valley, vacation rental in Chatham

Quiet Guest House In The Green River Valley

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Cabin on forest road, vacation rental in Chatham

Cabin on forest road

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Two Rooms with En-Suite in Quiet Woodland, vacation rental in Chatham

Two Rooms with En-Suite in Quiet Woodland

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

The Home in Malden Bridge, Columbia County, New York

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Carriage House Charmer, vacation rental in Chatham

Carriage House Charmer

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Historical Dutch Gem In The Hudson Valley, vacation rental in Chatham

Historical Dutch Gem In The Hudson Valley

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Private Hillsdale Home With Views Of Catamount., vacation rental in Chatham

Private Hillsdale Home With Views Of Catamount.

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

Hudson River Beach House

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lakefront Chalet perfect for families!, vacation rental in Chatham

Lakefront Chalet perfect for families!

4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Stunning New Construction All SeasonLakefront Home, vacation rental in 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 Chatham

Cozy apartment overlooking our small farm. Family Friendly.

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 Chatham

Secluded House with Picturesque Views in Historic Old Chatham, NY

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Sun-Drenched Property Steps from Warren, vacation rental in Chatham

Sun-Drenched Property Steps from Warren

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern Farm House Right Off Warren St., vacation rental in Chatham

Modern Farm House Right Off Warren St.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Family-Friendly Home, vacation rental in Chatham

Secluded Family-Friendly Home

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

Hillhouse Log Cabin

3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Roaring Rapids Cottage, vacation rental in 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 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 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 Chatham

Leisure home with beach front property

6 bedrooms
3 bathrooms
Sleeps 25
Match: Sleeps
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Bassinova-on-Hudson, vacation rental in Chatham

Bassinova-on-Hudson

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Historic Gem Near Hudson, NY, vacation rental in Chatham

Historic Gem Near Hudson, NY

1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Tentrr Signature Site - Berkshire Mountain Hideaway, vacation rental in Chatham

Tentrr Signature Site - Berkshire Mountain Hideaway

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Hudson Valley Berkshires Cottage, vacation rental in Chatham

Hudson Valley Berkshires Cottage

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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A Beautiful Retreat In a Stunning Home and Landscaped Lawns, vacation rental in Chatham

A Beautiful Retreat In a Stunning Home and Landscaped Lawns

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Chalet near 4 ski resorts with hot tub, vacation rental in 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 Chatham

Spacious secluded yet close to everything

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Winter Wonderland, minutes to Hudson and Berkshires, vacation rental in Chatham

Winter Wonderland, minutes to Hudson and Berkshires

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tentrr Signature Site - WATER + WOODS, vacation rental in Chatham

Tentrr Signature Site - WATER + WOODS

1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
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Tentrr Signature Site - The Lodge's Campsite, vacation rental in Chatham

Tentrr Signature Site - The Lodge's Campsite

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Nature Lover’s Haven: Ski, Golf, Fish, Hike & More, vacation rental in Chatham

Nature Lover’s Haven: Ski, Golf, Fish, Hike & More

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Cozy Retreat w/ Hot Tub on Sleepy Hollow Lake, vacation rental in Chatham

NEW! Cozy Retreat w/ Hot Tub on Sleepy Hollow Lake

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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