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Holiday Homes in Chappaqua

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50 rentals in Chappaqua.
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Full Cottage at a Home from 1820, holiday rental in Chappaqua

Full Cottage at a Home from 1820

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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SHORELINE HOLIDAY GETAWAY BIG YARD FIREPLACE, holiday rental in Chappaqua

SHORELINE HOLIDAY GETAWAY BIG YARD FIREPLACE

6 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Private 3.5 acre estate  Zen House /Historic mid century modern  / lap pool, holiday rental in Chappaqua

Private 3.5 acre estate Zen House /Historic mid century modern / lap pool

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Lakeside Modern Farmhouse/Craftsman Chalet, holiday rental in Chappaqua

Lakeside Modern Farmhouse/Craftsman Chalet

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Greenwich /New Construction/Hotel Alternative, holiday rental in Chappaqua

Greenwich /New Construction/Hotel Alternative

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Charming and immaculate 3 br duplex!, holiday rental in Chappaqua

Charming and immaculate 3 br duplex!

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Great hotel alternative!!! Brand New!!! 3 Bedroom Home - Heart of Greenwich, holiday rental in Chappaqua

Great hotel alternative!!! Brand New!!! 3 Bedroom Home - Heart of Greenwich

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Centrally Located Townhouse - Hotel Alternative -close to town - Pet friendly, holiday rental in Chappaqua

Centrally Located Townhouse - Hotel Alternative -close to town - Pet friendly

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Castle By The Lake, holiday rental in Chappaqua

Castle By The Lake

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Bear Mountain House., holiday rental in Chappaqua

Bear Mountain House.

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Holiday cozy country cottage!, holiday rental in Chappaqua

Holiday cozy country cottage!

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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The beautiful HillSide Cottage awaits you!  Great location and close to NY city!, holiday rental in Chappaqua

The beautiful HillSide Cottage awaits you! Great location and close to NY city!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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5-Br 3-bath Skylit Home on 3 Forested Acres, holiday rental in Chappaqua

5-Br 3-bath Skylit Home on 3 Forested Acres

5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Serene Connecticut Retreat - Luxury 2 bedroom apt, holiday rental in Chappaqua

Serene Connecticut Retreat - Luxury 2 bedroom apt

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Quaint and immaculate 3 br duplex!, holiday rental in Chappaqua

Quaint and immaculate 3 br duplex!

3 bedrooms
2 bathrooms
Sleeps 5
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North Stamford Guest House, holiday rental in Chappaqua

North Stamford Guest House

2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Croton Lodge: Luxury 2bd⭐Comfort+Style⭐45min to NYC., holiday rental in Chappaqua

Croton Lodge: Luxury 2bd⭐Comfort+Style⭐45min to NYC.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Brand New! Walk to Train, Downtown Fully Loaded, holiday rental in Chappaqua

Brand New! Walk to Train, Downtown Fully Loaded

3 bedrooms
5 bathrooms
Sleeps 5
Match: Sleeps
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Back Country Estate with Pool - Greenwich CT, holiday rental in Chappaqua

Back Country Estate with Pool - Greenwich CT

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Quaint Yonkers Condo - 1 Block to Hudson River!, holiday rental in Chappaqua

Quaint Yonkers Condo - 1 Block to Hudson River!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Twenty One ! Boutique Stay in Heart of Downtown, holiday rental in Chappaqua

Twenty One ! Boutique Stay in Heart of Downtown

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Modern,CloseToMetro/City,4BR/2BA, Free Parking- 35 minutes to NYC, holiday rental in Chappaqua

Modern,CloseToMetro/City,4BR/2BA, Free Parking- 35 minutes to NYC

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Dominique's NYC Unique  2 Bedroom Pad-metro*wifi*safe neighborhood*quiet apt*, holiday rental in Chappaqua

Dominique's NYC Unique 2 Bedroom Pad-metro*wifi*safe neighborhood*quiet apt*

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Faces The Hudson + Only An Hour Outside NYC, holiday rental in Chappaqua

Faces The Hudson + Only An Hour Outside NYC

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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'THE HILLTOP'-40Mins From NYC- Private Estate, holiday rental in Chappaqua

'THE HILLTOP'-40Mins From NYC- Private Estate

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Charming Rye Colonial Walk to Town & Train, holiday rental in Chappaqua

Charming Rye Colonial Walk to Town & Train

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Valhalla Sky 1 Queenn Rm, holiday rental in Chappaqua

Valhalla Sky 1 Queenn Rm

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Modern Comfy Studio 30 min from Manhattan - Yonkers NY, holiday rental in Chappaqua

Modern Comfy Studio 30 min from Manhattan - Yonkers NY

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Woodland Serenity near West Point & hiking trails, Cold Spring, Beacon!, holiday rental in Chappaqua

Woodland Serenity near West Point & hiking trails, Cold Spring, Beacon!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Enchanting Hudson Valley Cottage Near Hiking!, holiday rental in Chappaqua

Enchanting Hudson Valley Cottage Near Hiking!

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Family House on Hudson River - 9 Mi. to West Point, holiday rental in Chappaqua

Family House on Hudson River - 9 Mi. to West Point

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Downing Wood, holiday rental in Chappaqua

Tentrr Signature Site - Downing Wood

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Private House; Golf, Hike, Fish, Swim, Relax, holiday rental in Chappaqua

Beautiful Private House; Golf, Hike, Fish, Swim, Relax

2 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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One of a Kind Cotswold Summer Retreat on 18 Secluded Acres, holiday rental in Chappaqua

One of a Kind Cotswold Summer Retreat on 18 Secluded Acres

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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An elegant rustic home/lodge set on 20 acres and 45 miles from NYC, holiday rental in Chappaqua

An elegant rustic home/lodge set on 20 acres and 45 miles from NYC

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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White Plains Prospect Park Winter Rental 1-3 Months, holiday rental in Chappaqua

White Plains Prospect Park Winter Rental 1-3 Months

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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DOMIR Garrison log cabin +hot tub+barrel sauna, holiday rental in Chappaqua

DOMIR Garrison log cabin +hot tub+barrel sauna

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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La Casita Bonita Near NYC, holiday rental in Chappaqua

La Casita Bonita Near NYC

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Private Getaway <2 Mi to Croton Falls Station, holiday rental in Chappaqua

NEW! Private Getaway <2 Mi to Croton Falls Station

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Greenwich Hotel Alternative / Boutique Living  - Fully Loaded- Turn Key 1B, holiday rental in Chappaqua

Greenwich Hotel Alternative / Boutique Living - Fully Loaded- Turn Key 1B

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Sophisticated Country Living, holiday rental in Chappaqua

Sophisticated Country Living

4 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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Walker's Paradise Steps from Greenwich Ave, holiday rental in Chappaqua

Walker's Paradise Steps from Greenwich Ave

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Emerald's Farm, holiday rental in Chappaqua

Emerald's Farm

5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Heart of Greenwich - Sun Drenched and Relaxing, holiday rental in Chappaqua

Heart of Greenwich - Sun Drenched and Relaxing

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bright & Airy Apartment w/ Balcony ~20 Mi to NYC!, holiday rental in Chappaqua

Bright & Airy Apartment w/ Balcony ~20 Mi to NYC!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Comfy and Stylish Harbor Point Studio, holiday rental in Chappaqua

Comfy and Stylish Harbor Point Studio

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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The Perfect Studio Getaway

0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
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The Perfect Studio Getaway

0 bedrooms
0 bathrooms
Sleeps 0
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Newly listed Property, Home away from Home, Close to restaurants and local beach, holiday rental in Chappaqua

Newly listed Property, Home away from Home, Close to restaurants and local beach

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Memory Lane Farm, holiday rental in Chappaqua

Memory Lane Farm

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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