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Chappaqua, NY Holiday Rentals, Apartments and Villas
Holiday Rentals
USA
New York (NY)
Westchester County
Chappaqua, NY Holiday Rentals, Apartments and Villas
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Internet or Wifi (43)
Air Conditioning (43)
Washer/Dryer (38)
Other outdoor space (27)
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Suitability
Kid friendly (39)
Pet friendly (21)
Smoking allowed (2)
Elder access (1)
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Holiday Rental House (36)
Condominium/Apartment (11)
Cabin Holiday Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (3)
Boat Available (1)
Private Chef (0)
Private Beach (0)
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Distance from
5 km
Chappaqua Performing Arts Center
Glazier Arboretum
Gedney Park
Grace Baptist Church
Emmary Day Spa
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47 rentals
in Chappaqua.
Family home in one of NY top-ranked school districts with Tennis court
Holiday Rental House
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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 House
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3 bedrooms
2 bathrooms
Sleeps 5
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The Best of Both Worlds: For nature lovers but close to New York City
2
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 5
Match:
Sleeps
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Tranquil Country Contemporary
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
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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
Condo/Apartment
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0 bedrooms
1 bathroom
Sleeps 4
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Cozy house on the Hudson
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Bright&Comfy 2bed/1ba in quiet White Plains duplex
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Neighbor's house - Welcome!
4
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Private Country Getaway
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
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Summer in Katonah. Walk to everything! Train to NYC.
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 8
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Amazing 3BR/3BA! Croton on Hudson!
Holiday Rental House
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1 bedroom
3 bathrooms
Sleeps 8
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Estate Home with Pool and Privacy for fun with family and pets!
Holiday Rental House
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4 bedrooms
7 bathrooms
Sleeps 8
Match:
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Gracious Country Home
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Newly Renovated Cozy 2 Bedroom Apartment with 3 min walk to Main Street
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 5
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Stunning views, 3-bedroom house in delightful Croton-on-Hudson with WiFi, AC
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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4 bedroom quiet contemp in armonk/greenwich
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 6
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Ossining Vacation Rental Near River, Trails & MTA!
Holiday Rental House
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7 bedrooms
4 bathrooms
Sleeps 11
Match:
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Hudson River Peaceful Getaway
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 5
Match:
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Camped Inn at Sundial Farm -- Tiny House
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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Huge Private Floor packed full! Super quiet and relaxing!
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 6
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Luxury 8 BR Estate with Pool and Tennis court
Holiday Rental House
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8 bedrooms
9 bathrooms
Sleeps 16
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Spectacular Mansion with pool/spa - close to NYC
Holiday Rental House
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4 bedrooms
6 bathrooms
Sleeps 12
Match:
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Cozy 2 Bedroom 1 bath, walking dustance from all the fun!
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 3
Match:
Sleeps
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Enjoy the best of both worlds
Condo/Apartment
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3 bedrooms
3 bathrooms
Sleeps 4
Match:
Sleeps
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Sleepy Hollow - Upstate Castle - BBQ Events Games
Holiday Rental House
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7 bedrooms
5 bathrooms
Sleeps 13
Match:
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Beautiful Back Country Home on 20 acres! Ultra Private and Exclusive!
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
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Amazing Large Private Studio!+
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 6
Match:
Sleeps
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Luxury Hudson River Retreat- quaint town, nature & NYC nearby.
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 2
Match:
Sleeps
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Charming Elmsford Home ~ 23 Mi to Manhattan!
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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Round Hill Road Estate Home with 5 open acres
Holiday Rental House
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6 bedrooms
7 bathrooms
Sleeps 8
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Stunning spacious two-bedroom apartment, offers modern comfort and style.
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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The Red Hill Retreat - Woods Water History Privacy
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
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Clean, Comfy & Convenient 1 Bed Apt in the Village
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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White Plains Midterm Jacuzzi Heated Pool Game Room
Holiday Rental House
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7 bedrooms
6 bathrooms
Sleeps 15
Match:
Sleeps
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Cozy Cottage Get Away
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
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Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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Modern charming country cottage for long term availability
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 4
Match:
Sleeps
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Great Country Cottage
Holiday Rental House
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1 bedroom
2 bathrooms
Sleeps 2
Match:
Sleeps
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Cozy Lake House just an hour from NYC!
Holiday Rental House
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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
4
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
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Beautiful Private House; Golf, Hike, Fish, Swim, Relax
Holiday Rental House
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2 bedrooms
4 bathrooms
Sleeps 4
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Lovely cottage, ideal location
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Garden Studio with Private Full Bath & Sauna. Self check-in.
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Briarcliff Manor Estate w/ Hudson River Views
Holiday Rental House
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4 bedrooms
6 bathrooms
Sleeps 10
Match:
Sleeps
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Organic Oasis with Pool and Tennis!
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 5
Match:
Sleeps
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Stone Manor
Holiday Rental House
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4 bedrooms
6 bathrooms
Sleeps 10
Match:
Sleeps
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2BDRM COTTAGE IN PLEASANTVILLE
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 2
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Showing results 1-47 of 47
Frequently Asked Questions about Chappaqua
Do any holiday rentals in Chappaqua have a pool?
Yes, here are some popular holiday rentals in Chappaqua that have a pool:
Family home in one of NY top-ranked school districts with Tennis court
Charming 3-bedroom house in enchanting Chappaqua with WiFi, AC and Sanctuary.
Tranquil Country Contemporary
See all holiday rentals with a pool in Chappaqua on Tripadvisor
Do any holiday rentals in Chappaqua have internet access?
Yes, here are some popular holiday rentals in Chappaqua that have internet access:
Family home in one of NY top-ranked school districts with Tennis court
Charming 3-bedroom house in enchanting Chappaqua with WiFi, AC and Sanctuary.
Tranquil Country Contemporary
See all holiday rentals in Chappaqua on Tripadvisor
What are the best pet friendly rentals in Chappaqua?
The best pet friendly rentals in Chappaqua are:
Charming 3-bedroom house in enchanting Chappaqua with WiFi, AC and Sanctuary.
Family home in one of NY top-ranked school districts with Tennis court
Tranquil Country Contemporary
See all pet friendly holiday rentals in Chappaqua on Tripadvisor
What are some great rentals in Chappaqua that are kid friendly?
Some of the most popular kid friendly rentals in Chappaqua are:
Family home in one of NY top-ranked school districts with Tennis court
Charming 3-bedroom house in enchanting Chappaqua with WiFi, AC and Sanctuary.
Tranquil Country Contemporary
See all kid friendly holiday rentals in Chappaqua on Tripadvisor
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