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Chappaqua Holiday Apartments

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Bedrooms

Bathrooms

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5 km
47 rentals in Chappaqua.
Family home in one of NY top-ranked school districts with Tennis court, holiday rental in Chappaqua
Family home in one of NY top-ranked school districts with Tennis court, holiday rental in Chappaqua
Family home in one of NY top-ranked school districts with Tennis court, holiday rental in Chappaqua

Family home in one of NY top-ranked school districts with Tennis court

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Charming 3-bedroom house in enchanting Chappaqua with WiFi, AC and Sanctuary., holiday rental in Chappaqua
Charming 3-bedroom house in enchanting Chappaqua with WiFi, AC and Sanctuary., holiday rental in Chappaqua
Charming 3-bedroom house in enchanting Chappaqua with WiFi, AC and Sanctuary., holiday rental in Chappaqua

Charming 3-bedroom house in enchanting Chappaqua with WiFi, AC and Sanctuary.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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The Best of Both Worlds: For nature lovers but close to New York City, holiday rental in Chappaqua
The Best of Both Worlds: For nature lovers but close to New York City, holiday rental in Chappaqua
The Best of Both Worlds: For nature lovers but close to New York City, holiday rental in Chappaqua

The Best of Both Worlds: For nature lovers but close to New York City

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Tranquil Country Contemporary, holiday rental in Chappaqua
Tranquil Country Contemporary, holiday rental in Chappaqua
Tranquil Country Contemporary, holiday rental in Chappaqua

Tranquil Country Contemporary

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The following properties within 32 kms of Chappaqua match all your filters:
Brand new private Studio in the heart of Tarrytown, holiday rental in Chappaqua
Brand new private Studio in the heart of Tarrytown, holiday rental in Chappaqua
Brand new private Studio in the heart of Tarrytown, holiday rental in Chappaqua

Brand new private Studio in the heart of Tarrytown

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy house on the Hudson, holiday rental in Chappaqua
Cozy house on the Hudson, holiday rental in Chappaqua
Cozy house on the Hudson, holiday rental in Chappaqua

Cozy house on the Hudson

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bright&Comfy 2bed/1ba in quiet White Plains duplex, holiday rental in Chappaqua
Bright&Comfy 2bed/1ba in quiet White Plains duplex, holiday rental in Chappaqua
Bright&Comfy 2bed/1ba in quiet White Plains duplex, holiday rental in Chappaqua

Bright&Comfy 2bed/1ba in quiet White Plains duplex

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Neighbor's house - Welcome!, holiday rental in Chappaqua
Neighbor's house - Welcome!, holiday rental in Chappaqua
Neighbor's house - Welcome!, holiday rental in Chappaqua

Neighbor's house - Welcome!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Country Getaway, holiday rental in Chappaqua
Private Country Getaway, holiday rental in Chappaqua
Private Country Getaway, holiday rental in Chappaqua

Private Country Getaway

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Summer in Katonah. Walk to everything! Train to NYC., holiday rental in Chappaqua
Summer in Katonah. Walk to everything! Train to NYC., holiday rental in Chappaqua
Summer in Katonah. Walk to everything! Train to NYC., holiday rental in Chappaqua

Summer in Katonah. Walk to everything! Train to NYC.

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Amazing 3BR/3BA! Croton on Hudson!, holiday rental in Chappaqua
Amazing 3BR/3BA! Croton on Hudson!, holiday rental in Chappaqua
Amazing 3BR/3BA! Croton on Hudson!, holiday rental in Chappaqua

Amazing 3BR/3BA! Croton on Hudson!

Holiday Rental House
1 bedroom
3 bathrooms
Sleeps 8
Match: Sleeps
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Estate Home with Pool and Privacy for fun with family and pets!, holiday rental in Chappaqua
Estate Home with Pool and Privacy for fun with family and pets!, holiday rental in Chappaqua
Estate Home with Pool and Privacy for fun with family and pets!, holiday rental in Chappaqua

Estate Home with Pool and Privacy for fun with family and pets!

Holiday Rental House
4 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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Gracious Country Home, holiday rental in Chappaqua
Gracious Country Home, holiday rental in Chappaqua
Gracious Country Home, holiday rental in Chappaqua

Gracious Country Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Newly Renovated Cozy 2 Bedroom Apartment with 3 min walk to Main Street, holiday rental in Chappaqua
Newly Renovated Cozy 2 Bedroom Apartment with 3 min walk to Main Street, holiday rental in Chappaqua
Newly Renovated Cozy 2 Bedroom Apartment with 3 min walk to Main Street, holiday rental in Chappaqua

Newly Renovated Cozy 2 Bedroom Apartment with 3 min walk to Main Street

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Stunning views, 3-bedroom house in delightful Croton-on-Hudson with WiFi, AC, holiday rental in Chappaqua
Stunning views, 3-bedroom house in delightful Croton-on-Hudson with WiFi, AC, holiday rental in Chappaqua
Stunning views, 3-bedroom house in delightful Croton-on-Hudson with WiFi, AC, holiday rental in Chappaqua

Stunning views, 3-bedroom house in delightful Croton-on-Hudson with WiFi, AC

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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4 bedroom quiet contemp in armonk/greenwich, holiday rental in Chappaqua
4 bedroom quiet contemp in armonk/greenwich, holiday rental in Chappaqua
4 bedroom quiet contemp in armonk/greenwich, holiday rental in Chappaqua

4 bedroom quiet contemp in armonk/greenwich

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Ossining Vacation Rental Near River, Trails & MTA!, holiday rental in Chappaqua
Ossining Vacation Rental Near River, Trails & MTA!, holiday rental in Chappaqua
Ossining Vacation Rental Near River, Trails & MTA!, holiday rental in Chappaqua

Ossining Vacation Rental Near River, Trails & MTA!

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Hudson River Peaceful Getaway, holiday rental in Chappaqua
Hudson River Peaceful Getaway, holiday rental in Chappaqua
Hudson River Peaceful Getaway, holiday rental in Chappaqua

Hudson River Peaceful Getaway

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Camped Inn at Sundial Farm -- Tiny House, holiday rental in Chappaqua
Camped Inn at Sundial Farm -- Tiny House, holiday rental in Chappaqua
Camped Inn at Sundial Farm -- Tiny House, holiday rental in Chappaqua

Camped Inn at Sundial Farm -- Tiny House

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Huge Private Floor packed full!  Super quiet and relaxing!, holiday rental in Chappaqua
Huge Private Floor packed full!  Super quiet and relaxing!, holiday rental in Chappaqua
Huge Private Floor packed full!  Super quiet and relaxing!, holiday rental in Chappaqua

Huge Private Floor packed full! Super quiet and relaxing!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Luxury 8 BR Estate with Pool and Tennis court, holiday rental in Chappaqua
Luxury 8 BR Estate with Pool and Tennis court, holiday rental in Chappaqua
Luxury 8 BR Estate with Pool and Tennis court, holiday rental in Chappaqua

Luxury 8 BR Estate with Pool and Tennis court

Holiday Rental House
8 bedrooms
9 bathrooms
Sleeps 16
Match: Sleeps
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Spectacular Mansion with pool/spa - close to NYC, holiday rental in Chappaqua
Spectacular Mansion with pool/spa - close to NYC, holiday rental in Chappaqua
Spectacular Mansion with pool/spa - close to NYC, holiday rental in Chappaqua

Spectacular Mansion with pool/spa - close to NYC

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Cozy 2 Bedroom 1 bath, walking dustance from all the fun!, holiday rental in Chappaqua
Cozy 2 Bedroom 1 bath, walking dustance from all the fun!, holiday rental in Chappaqua
Cozy 2 Bedroom 1 bath, walking dustance from all the fun!, holiday rental in Chappaqua

Cozy 2 Bedroom 1 bath, walking dustance from all the fun!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Enjoy the best of both worlds, holiday rental in Chappaqua
Enjoy the best of both worlds, holiday rental in Chappaqua
Enjoy the best of both worlds, holiday rental in Chappaqua

Enjoy the best of both worlds

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Sleepy Hollow - Upstate Castle - BBQ Events Games, holiday rental in Chappaqua
Sleepy Hollow - Upstate Castle - BBQ Events Games, holiday rental in Chappaqua
Sleepy Hollow - Upstate Castle - BBQ Events Games, holiday rental in Chappaqua

Sleepy Hollow - Upstate Castle - BBQ Events Games

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
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Beautiful Back Country Home on 20 acres! Ultra Private and Exclusive!, holiday rental in Chappaqua
Beautiful Back Country Home on 20 acres! Ultra Private and Exclusive!, holiday rental in Chappaqua
Beautiful Back Country Home on 20 acres! Ultra Private and Exclusive!, holiday rental in Chappaqua

Beautiful Back Country Home on 20 acres! Ultra Private and Exclusive!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Amazing Large Private Studio!+, holiday rental in Chappaqua
Amazing Large Private Studio!+, holiday rental in Chappaqua
Amazing Large Private Studio!+, holiday rental in Chappaqua

Amazing Large Private Studio!+

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Luxury Hudson River Retreat- quaint town, nature & NYC nearby., holiday rental in Chappaqua
Luxury Hudson River Retreat- quaint town, nature & NYC nearby., holiday rental in Chappaqua
Luxury Hudson River Retreat- quaint town, nature & NYC nearby., holiday rental in Chappaqua

Luxury Hudson River Retreat- quaint town, nature & NYC nearby.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Charming Elmsford Home ~ 23 Mi to Manhattan!, holiday rental in Chappaqua
Charming Elmsford Home ~ 23 Mi to Manhattan!, holiday rental in Chappaqua
Charming Elmsford Home ~ 23 Mi to Manhattan!, holiday rental in Chappaqua

Charming Elmsford Home ~ 23 Mi to Manhattan!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Round Hill Road Estate Home with 5 open acres, holiday rental in Chappaqua
Round Hill Road Estate Home with 5 open acres, holiday rental in Chappaqua
Round Hill Road Estate Home with 5 open acres, holiday rental in Chappaqua

Round Hill Road Estate Home with 5 open acres

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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Stunning spacious two-bedroom apartment, offers modern comfort and style., holiday rental in Chappaqua
Stunning spacious two-bedroom apartment, offers modern comfort and style., holiday rental in Chappaqua
Stunning spacious two-bedroom apartment, offers modern comfort and style., holiday rental in Chappaqua

Stunning spacious two-bedroom apartment, offers modern comfort and style.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Red Hill Retreat - Woods Water History Privacy, holiday rental in Chappaqua
The Red Hill Retreat - Woods Water History Privacy, holiday rental in Chappaqua
The Red Hill Retreat - Woods Water History Privacy, holiday rental in Chappaqua

The Red Hill Retreat - Woods Water History Privacy

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Clean, Comfy & Convenient 1 Bed Apt in the Village, holiday rental in Chappaqua
Clean, Comfy & Convenient 1 Bed Apt in the Village, holiday rental in Chappaqua
Clean, Comfy & Convenient 1 Bed Apt in the Village, holiday rental in Chappaqua

Clean, Comfy & Convenient 1 Bed Apt in the Village

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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White Plains Midterm Jacuzzi Heated Pool Game Room, holiday rental in Chappaqua
White Plains Midterm Jacuzzi Heated Pool Game Room, holiday rental in Chappaqua
White Plains Midterm Jacuzzi Heated Pool Game Room, holiday rental in Chappaqua

White Plains Midterm Jacuzzi Heated Pool Game Room

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
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Cozy Cottage Get Away, holiday rental in Chappaqua
Cozy Cottage Get Away, holiday rental in Chappaqua
Cozy Cottage Get Away, holiday rental in Chappaqua

Cozy Cottage Get Away

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food, holiday rental in Chappaqua
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food, holiday rental in Chappaqua
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food, holiday rental in Chappaqua

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Modern charming country cottage for long term availability, holiday rental in Chappaqua
Modern charming country cottage for long term availability, holiday rental in Chappaqua
Modern charming country cottage for long term availability, holiday rental in Chappaqua

Modern charming country cottage for long term availability

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Great Country Cottage, holiday rental in Chappaqua
Great Country Cottage, holiday rental in Chappaqua
Great Country Cottage, holiday rental in Chappaqua

Great Country Cottage

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Cozy Lake House just an hour from NYC!, holiday rental in Chappaqua
Cozy Lake House just an hour from NYC!, holiday rental in Chappaqua
Cozy Lake House just an hour from NYC!, holiday rental in Chappaqua

Cozy Lake House just an hour from NYC!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Back Country Estate w/ Pool, Sleeps 8 - Fully loaded, Pet Friendly Greenwich CT, holiday rental in Chappaqua
Back Country Estate w/ Pool, Sleeps 8 - Fully loaded, Pet Friendly Greenwich CT, holiday rental in Chappaqua
Back Country Estate w/ Pool, Sleeps 8 - Fully loaded, Pet Friendly Greenwich CT, holiday rental in Chappaqua

Back Country Estate w/ Pool, Sleeps 8 - Fully loaded, Pet Friendly Greenwich CT

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
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, holiday rental in Chappaqua
Beautiful Private House; Golf, Hike, Fish, Swim, Relax, holiday rental in Chappaqua

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

Holiday Rental House
2 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
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Lovely cottage, ideal location, holiday rental in Chappaqua
Lovely cottage, ideal location, holiday rental in Chappaqua
Lovely cottage, ideal location, holiday rental in Chappaqua

Lovely cottage, ideal location

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Garden Studio with Private Full Bath & Sauna. Self check-in., holiday rental in Chappaqua
Garden Studio with Private Full Bath & Sauna. Self check-in., holiday rental in Chappaqua
Garden Studio with Private Full Bath & Sauna. Self check-in., holiday rental in Chappaqua

Garden Studio with Private Full Bath & Sauna. Self check-in.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Briarcliff Manor Estate w/ Hudson River Views, holiday rental in Chappaqua
Briarcliff Manor Estate w/ Hudson River Views, holiday rental in Chappaqua
Briarcliff Manor Estate w/ Hudson River Views, holiday rental in Chappaqua

Briarcliff Manor Estate w/ Hudson River Views

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Organic Oasis with Pool and Tennis!, holiday rental in Chappaqua
Organic Oasis with Pool and Tennis!, holiday rental in Chappaqua
Organic Oasis with Pool and Tennis!, holiday rental in Chappaqua

Organic Oasis with Pool and Tennis!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Stone Manor, holiday rental in Chappaqua
Stone Manor, holiday rental in Chappaqua
Stone Manor, holiday rental in Chappaqua

Stone Manor

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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2BDRM COTTAGE IN PLEASANTVILLE, holiday rental in Chappaqua
2BDRM COTTAGE IN PLEASANTVILLE, holiday rental in Chappaqua
2BDRM COTTAGE IN PLEASANTVILLE, holiday rental in Chappaqua

2BDRM COTTAGE IN PLEASANTVILLE

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Showing results 1-47 of 47
Frequently Asked Questions about Chappaqua