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Chappaqua Vacation Rentals

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50 rentals in Chappaqua.
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The Best of Both Worlds: For nature lovers but close to New York City, vacation rental in Chappaqua
The Best of Both Worlds: For nature lovers but close to New York City, vacation rental in Chappaqua
The Best of Both Worlds: For nature lovers but close to New York City, vacation 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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Family home in one of NY top-ranked school districts with Tennis court, vacation rental in Chappaqua
Family home in one of NY top-ranked school districts with Tennis court, vacation rental in Chappaqua
Family home in one of NY top-ranked school districts with Tennis court, vacation 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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Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food, vacation rental in Chappaqua
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food, vacation rental in Chappaqua
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food, vacation rental in Chappaqua

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

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Luxury home filled with books and art, with great access. Sleeps up to fourteen., vacation rental in Chappaqua
Luxury home filled with books and art, with great access. Sleeps up to fourteen., vacation rental in Chappaqua
Luxury home filled with books and art, with great access. Sleeps up to fourteen., vacation rental in Chappaqua

Luxury home filled with books and art, with great access. Sleeps up to fourteen.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Cozy house on the Hudson, vacation rental in Chappaqua
Cozy house on the Hudson, vacation rental in Chappaqua
Cozy house on the Hudson, vacation rental in Chappaqua

Cozy house on the Hudson

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Need a place to relax and enjoy your vacation stay at The Cozy Den, vacation rental in Chappaqua
Need a place to relax and enjoy your vacation stay at The Cozy Den, vacation rental in Chappaqua
Need a place to relax and enjoy your vacation stay at The Cozy Den, vacation rental in Chappaqua

Need a place to relax and enjoy your vacation stay at The Cozy Den

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Perfect Studio Getaway, vacation rental in Chappaqua
The Perfect Studio Getaway, vacation rental in Chappaqua
The Perfect Studio Getaway, vacation rental in Chappaqua

The Perfect Studio Getaway

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury 8 BR Estate with Pool and Tennis court, vacation rental in Chappaqua
Luxury 8 BR Estate with Pool and Tennis court, vacation rental in Chappaqua
Luxury 8 BR Estate with Pool and Tennis court, vacation 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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5-Br 3-bath Skylit Home on 3 Forested Acres, vacation rental in Chappaqua
5-Br 3-bath Skylit Home on 3 Forested Acres, vacation rental in Chappaqua
5-Br 3-bath Skylit Home on 3 Forested Acres, vacation rental in Chappaqua

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

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 11
Match: Sleeps
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Greenwich Back Country Farm House, Brand New, Amazing property, private escape!!, vacation rental in Chappaqua
Greenwich Back Country Farm House, Brand New, Amazing property, private escape!!, vacation rental in Chappaqua
Greenwich Back Country Farm House, Brand New, Amazing property, private escape!!, vacation rental in Chappaqua

Greenwich Back Country Farm House, Brand New, Amazing property, private escape!!

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Holiday cozy country cottage!, vacation rental in Chappaqua
Holiday cozy country cottage!, vacation rental in Chappaqua
Holiday cozy country cottage!, vacation rental in Chappaqua

Holiday cozy country cottage!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Neighbor's House -- Welcome!, vacation rental in Chappaqua
Neighbor's House -- Welcome!, vacation rental in Chappaqua
Neighbor's House -- Welcome!, vacation rental in Chappaqua

Neighbor's House -- Welcome!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Back Country Estate with Pool - Greenwich CT, vacation rental in Chappaqua
Back Country Estate with Pool - Greenwich CT, vacation rental in Chappaqua
Back Country Estate with Pool - Greenwich CT, vacation rental in Chappaqua

Back Country Estate with Pool - Greenwich CT

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Westchester Castle: A Luxury Retreat for Your Family, vacation rental in Chappaqua
Westchester Castle: A Luxury Retreat for Your Family, vacation rental in Chappaqua
Westchester Castle: A Luxury Retreat for Your Family, vacation rental in Chappaqua

Westchester Castle: A Luxury Retreat for Your Family

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
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⭐️❤️Historic Town ⭐️ Bridge View ⭐️ Walk Everywhere ⭐️ Quick Train to NYC, vacation rental in Chappaqua
⭐️❤️Historic Town ⭐️ Bridge View ⭐️ Walk Everywhere ⭐️ Quick Train to NYC, vacation rental in Chappaqua
⭐️❤️Historic Town ⭐️ Bridge View ⭐️ Walk Everywhere ⭐️ Quick Train to NYC, vacation rental in Chappaqua

⭐️❤️Historic Town ⭐️ Bridge View ⭐️ Walk Everywhere ⭐️ Quick Train to NYC

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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★10 Top Rated Town ★ Bridge View ★ Train to NYC!, vacation rental in Chappaqua
★10 Top Rated Town ★ Bridge View ★ Train to NYC!, vacation rental in Chappaqua
★10 Top Rated Town ★ Bridge View ★ Train to NYC!, vacation rental in Chappaqua

★10 Top Rated Town ★ Bridge View ★ Train to NYC!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Gorgeous 2 BR with private garden, walk to town, vacation rental in Chappaqua
Gorgeous 2 BR with private garden, walk to town, vacation rental in Chappaqua
Gorgeous 2 BR with private garden, walk to town, vacation rental in Chappaqua

Gorgeous 2 BR with private garden, walk to town

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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A new 1BR close to White Plains Train Station, vacation rental in Chappaqua
A new 1BR close to White Plains Train Station, vacation rental in Chappaqua
A new 1BR close to White Plains Train Station, vacation rental in Chappaqua

A new 1BR close to White Plains Train Station

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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�⭐️❤️Large & Gated Deck w/ Views of Tappan Zee Bridge⭐️❤️ Close to NYC Train❤️, vacation rental in Chappaqua
�⭐️❤️Large & Gated Deck w/ Views of Tappan Zee Bridge⭐️❤️ Close to NYC Train❤️, vacation rental in Chappaqua
�⭐️❤️Large & Gated Deck w/ Views of Tappan Zee Bridge⭐️❤️ Close to NYC Train❤️, vacation rental in Chappaqua

�⭐️❤️Large & Gated Deck w/ Views of Tappan Zee Bridge⭐️❤️ Close to NYC Train❤️

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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★FREE Parking★Deck★Tarrytown★FASTwifi★RokuTV★Train to New York City, vacation rental in Chappaqua
★FREE Parking★Deck★Tarrytown★FASTwifi★RokuTV★Train to New York City, vacation rental in Chappaqua
★FREE Parking★Deck★Tarrytown★FASTwifi★RokuTV★Train to New York City, vacation rental in Chappaqua

★FREE Parking★Deck★Tarrytown★FASTwifi★RokuTV★Train to New York City

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Tranquil Country Contemporary, vacation rental in Chappaqua
Tranquil Country Contemporary, vacation rental in Chappaqua
Tranquil Country Contemporary, vacation rental in Chappaqua

Tranquil Country Contemporary

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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A dream summer rental 30 miles from New York City in picturesque Bedford, NY!, vacation rental in Chappaqua
A dream summer rental 30 miles from New York City in picturesque Bedford, NY!, vacation rental in Chappaqua
A dream summer rental 30 miles from New York City in picturesque Bedford, NY!, vacation rental in Chappaqua

A dream summer rental 30 miles from New York City in picturesque Bedford, NY!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Round Hill Road Estate Home with 5 open acres, vacation rental in Chappaqua
Round Hill Road Estate Home with 5 open acres, vacation rental in Chappaqua
Round Hill Road Estate Home with 5 open acres, vacation 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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Beautiful Private House; Golf, Hike, Fish, Swim, Relax, vacation rental in Chappaqua
Beautiful Private House; Golf, Hike, Fish, Swim, Relax, vacation rental in Chappaqua
Beautiful Private House; Golf, Hike, Fish, Swim, Relax, vacation 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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Rent Private Home w/ Pool close to town, vacation rental in Chappaqua
Rent Private Home w/ Pool close to town, vacation rental in Chappaqua
Rent Private Home w/ Pool close to town, vacation rental in Chappaqua

Rent Private Home w/ Pool close to town

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Bedford Post, A Luxury Authentic Country Inn Just An Hour From Manhattan, vacation rental in Chappaqua
Bedford Post, A Luxury Authentic Country Inn Just An Hour From Manhattan, vacation rental in Chappaqua
Bedford Post, A Luxury Authentic Country Inn Just An Hour From Manhattan, vacation rental in Chappaqua

Bedford Post, A Luxury Authentic Country Inn Just An Hour From Manhattan

Holiday Rental House
8 bedrooms
10 bathrooms
Sleeps 16
Match: Sleeps
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Cozy Cottage Get Away, vacation rental in Chappaqua
Cozy Cottage Get Away, vacation rental in Chappaqua
Cozy Cottage Get Away, vacation rental in Chappaqua

Cozy Cottage Get Away

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Perfect Studio Getaway, vacation rental in Chappaqua
The Perfect Studio Getaway, vacation rental in Chappaqua
The Perfect Studio Getaway, vacation rental in Chappaqua

The Perfect Studio Getaway

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Upscale Two Bedroom Apartment | Fully Furnished | Downtown White Plains, vacation rental in Chappaqua
Upscale Two Bedroom Apartment | Fully Furnished | Downtown White Plains, vacation rental in Chappaqua
Upscale Two Bedroom Apartment | Fully Furnished | Downtown White Plains, vacation rental in Chappaqua

Upscale Two Bedroom Apartment | Fully Furnished | Downtown White Plains

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Lovely 3-bedroom rental unit outside of NYC, vacation rental in Chappaqua
Lovely 3-bedroom rental unit outside of NYC, vacation rental in Chappaqua
Lovely 3-bedroom rental unit outside of NYC, vacation rental in Chappaqua

Lovely 3-bedroom rental unit outside of NYC

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private Country Getaway, vacation rental in Chappaqua
Private Country Getaway, vacation rental in Chappaqua
Private Country Getaway, vacation rental in Chappaqua

Private Country Getaway

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Ossining Woodland Oasis ! 5 minutes from famous biking & hiking trails, vacation rental in Chappaqua
Beautiful Ossining Woodland Oasis ! 5 minutes from famous biking & hiking trails, vacation rental in Chappaqua
Beautiful Ossining Woodland Oasis ! 5 minutes from famous biking & hiking trails, vacation rental in Chappaqua

Beautiful Ossining Woodland Oasis ! 5 minutes from famous biking & hiking trails

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Beautiful apartment in great neighborhood., vacation rental in Chappaqua
Beautiful apartment in great neighborhood., vacation rental in Chappaqua
Beautiful apartment in great neighborhood., vacation rental in Chappaqua

Beautiful apartment in great neighborhood.

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Summer in Katonah. Walk to everything! Train to NYC., vacation rental in Chappaqua
Summer in Katonah. Walk to everything! Train to NYC., vacation rental in Chappaqua
Summer in Katonah. Walk to everything! Train to NYC., vacation 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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Large Gated Farm House with Huge Heated Pool on 4 Private Acres, vacation rental in Chappaqua
Large Gated Farm House with Huge Heated Pool on 4 Private Acres, vacation rental in Chappaqua
Large Gated Farm House with Huge Heated Pool on 4 Private Acres, vacation rental in Chappaqua

Large Gated Farm House with Huge Heated Pool on 4 Private Acres

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 13
Match: Sleeps
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Chic One Bedroom Apartment | Luxury Amenities | Downtown White Plains, vacation rental in Chappaqua
Chic One Bedroom Apartment | Luxury Amenities | Downtown White Plains, vacation rental in Chappaqua
Chic One Bedroom Apartment | Luxury Amenities | Downtown White Plains, vacation rental in Chappaqua

Chic One Bedroom Apartment | Luxury Amenities | Downtown White Plains

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Luxury Studio Apartment | Downtown White Plains | by GLS, vacation rental in Chappaqua
Luxury Studio Apartment | Downtown White Plains | by GLS, vacation rental in Chappaqua
Luxury Studio Apartment | Downtown White Plains | by GLS, vacation rental in Chappaqua

Luxury Studio Apartment | Downtown White Plains | by GLS

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Gracious Country Home, vacation rental in Chappaqua
Gracious Country Home, vacation rental in Chappaqua
Gracious Country Home, vacation rental in Chappaqua

Gracious Country Home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Unique 7-bd Oasis |10 min walk to NYC Express Train, vacation rental in Chappaqua
Unique 7-bd Oasis |10 min walk to NYC Express Train, vacation rental in Chappaqua
Unique 7-bd Oasis |10 min walk to NYC Express Train, vacation rental in Chappaqua

Unique 7-bd Oasis |10 min walk to NYC Express Train

Holiday Rental House
7 bedrooms
8 bathrooms
Sleeps 14
Match: Sleeps
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5 min to White Plains Train Station!, vacation rental in Chappaqua
5 min to White Plains Train Station!, vacation rental in Chappaqua
5 min to White Plains Train Station!, vacation rental in Chappaqua

5 min to White Plains Train Station!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Perfect Location w/ River Views Tarrytown 8 BR/4BA, vacation rental in Chappaqua
Perfect Location w/ River Views Tarrytown 8 BR/4BA, vacation rental in Chappaqua
Perfect Location w/ River Views Tarrytown 8 BR/4BA, vacation rental in Chappaqua

Perfect Location w/ River Views Tarrytown 8 BR/4BA

Holiday Rental House
8 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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Private 1BR Apt | Parking | Gym | White Plains, vacation rental in Chappaqua
Private 1BR Apt | Parking | Gym | White Plains, vacation rental in Chappaqua
Private 1BR Apt | Parking | Gym | White Plains, vacation rental in Chappaqua

Private 1BR Apt | Parking | Gym | White Plains

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Chic 1BR | Full Kitchen & Laundry | Downtown White Plains, vacation rental in Chappaqua
Chic 1BR | Full Kitchen & Laundry | Downtown White Plains, vacation rental in Chappaqua
Chic 1BR | Full Kitchen & Laundry | Downtown White Plains, vacation rental in Chappaqua

Chic 1BR | Full Kitchen & Laundry | Downtown White Plains

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Family Friendly 2BR | Full Kitchen | Downtown White Plains, vacation rental in Chappaqua
Family Friendly 2BR | Full Kitchen | Downtown White Plains, vacation rental in Chappaqua
Family Friendly 2BR | Full Kitchen | Downtown White Plains, vacation rental in Chappaqua

Family Friendly 2BR | Full Kitchen | Downtown White Plains

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Spacious Studio | Kitchen + Laundry | Downtown White Plains, vacation rental in Chappaqua
Spacious Studio | Kitchen + Laundry | Downtown White Plains, vacation rental in Chappaqua
Spacious Studio | Kitchen + Laundry | Downtown White Plains, vacation rental in Chappaqua

Spacious Studio | Kitchen + Laundry | Downtown White Plains

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Luxury Hudson River Retreat- quaint town, nature & NYC nearby., vacation rental in Chappaqua
Luxury Hudson River Retreat- quaint town, nature & NYC nearby., vacation rental in Chappaqua
Luxury Hudson River Retreat- quaint town, nature & NYC nearby., vacation 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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Victorian Farmhouse with Pool near NYC, vacation rental in Chappaqua
Victorian Farmhouse with Pool near NYC, vacation rental in Chappaqua
Victorian Farmhouse with Pool near NYC, vacation rental in Chappaqua

Victorian Farmhouse with Pool near NYC

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Modern 1BR Apt | Fitness Center | Downtown White Plains, vacation rental in Chappaqua
Modern 1BR Apt | Fitness Center | Downtown White Plains, vacation rental in Chappaqua
Modern 1BR Apt | Fitness Center | Downtown White Plains, vacation rental in Chappaqua

Modern 1BR Apt | Fitness Center | Downtown White Plains

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Memory Lane Farm, vacation rental in Chappaqua
Memory Lane Farm, vacation rental in Chappaqua
Memory Lane Farm, vacation rental in Chappaqua

Memory Lane Farm

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Room in private property, vacation rental in Chappaqua
Room in private property, vacation rental in Chappaqua
Room in private property, vacation rental in Chappaqua

Room in private property

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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