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Holiday Homes in Chappaqua

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Bedrooms

Bathrooms

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5 km
47 rentals in Chappaqua.
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
More info
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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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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
More info
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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 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
More info
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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
More info
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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
More info
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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
More info
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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
More info
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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
More info
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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
3 bedrooms
1 bathroom
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
More info
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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
More info
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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
More info
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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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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
More info
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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
More info
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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
More info
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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
More info
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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
More info
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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
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Relaxing & Great Location & Minutes from New York, holiday rental in Chappaqua
Relaxing & Great Location & Minutes from New York, holiday rental in Chappaqua
Relaxing & Great Location & Minutes from New York, holiday rental in Chappaqua

Relaxing & Great Location & Minutes from New York

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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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
More info
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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
More info
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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
More info
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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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4-bedroom Barn house with WiFi, Fireplace, Firepit, BBQ Grill by hiking trails, holiday rental in Chappaqua
4-bedroom Barn house with WiFi, Fireplace, Firepit, BBQ Grill by hiking trails, holiday rental in Chappaqua
4-bedroom Barn house with WiFi, Fireplace, Firepit, BBQ Grill by hiking trails, holiday rental in Chappaqua

4-bedroom Barn house with WiFi, Fireplace, Firepit, BBQ Grill by hiking trails

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming 2-bedroom apartment near downtown and Metro North- White Plains, holiday rental in Chappaqua
Charming 2-bedroom apartment near downtown and Metro North- White Plains, holiday rental in Chappaqua
Charming 2-bedroom apartment near downtown and Metro North- White Plains, holiday rental in Chappaqua

Charming 2-bedroom apartment near downtown and Metro North- White Plains

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Spacious Hudson Rivertown home in Tarrytown, NY, 8 guests, sleeps 10, holiday rental in Chappaqua
Spacious Hudson Rivertown home in Tarrytown, NY, 8 guests, sleeps 10, holiday rental in Chappaqua
Spacious Hudson Rivertown home in Tarrytown, NY, 8 guests, sleeps 10, holiday rental in Chappaqua

Spacious Hudson Rivertown home in Tarrytown, NY, 8 guests, sleeps 10

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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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
More info
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Hudson Valley Estate on 4 Acres w/ Private Pool!, holiday rental in Chappaqua
Hudson Valley Estate on 4 Acres w/ Private Pool!, holiday rental in Chappaqua
Hudson Valley Estate on 4 Acres w/ Private Pool!, holiday rental in Chappaqua

Hudson Valley Estate on 4 Acres w/ Private Pool!

Holiday Rental House
9 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
More info
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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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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
More info
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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
More info
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3 Mi to Downtown: Spacious White Plains Home, holiday rental in Chappaqua
3 Mi to Downtown: Spacious White Plains Home, holiday rental in Chappaqua
3 Mi to Downtown: Spacious White Plains Home, holiday rental in Chappaqua

3 Mi to Downtown: Spacious White Plains Home

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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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
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
More info
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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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Charming 2-bedroom apartment with AC, WiFi in lovely Tarrytown, holiday rental in Chappaqua
Charming 2-bedroom apartment with AC, WiFi in lovely Tarrytown, holiday rental in Chappaqua
Charming 2-bedroom apartment with AC, WiFi in lovely Tarrytown, holiday rental in Chappaqua

Charming 2-bedroom apartment with AC, WiFi in lovely Tarrytown

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Designer Home in Lower Hudson Valley, holiday rental in Chappaqua
Designer Home in Lower Hudson Valley, holiday rental in Chappaqua
Designer Home in Lower Hudson Valley, holiday rental in Chappaqua

Designer Home in Lower Hudson Valley

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Cozy Studio with reading nook, holiday rental in Chappaqua
Cozy Studio with reading nook, holiday rental in Chappaqua
Cozy Studio with reading nook, holiday rental in Chappaqua

Cozy Studio with reading nook

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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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
More info
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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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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
More info
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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
More info
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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
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Spacious & Sunny Single Family, holiday rental in Chappaqua
Spacious & Sunny Single Family, holiday rental in Chappaqua
Spacious & Sunny Single Family, holiday rental in Chappaqua

Spacious & Sunny Single Family

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Showing results 1-47 of 47
Frequently Asked Questions about Chappaqua