Search Vacation Homes in Chappaqua

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Chappaqua vacation homes

Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Highland Falls
10.0 out of 10, Exceptional, (2)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
$394 nightly
The price is $400
Dec 10 - Dec 11
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Greenwich
9.6 out of 10, Exceptional, (23)
"The property was beautiful and clean, very comfortable with a nice view of the lake! Our hosts were helpful and attentive without being intrusive in any way. Our stay was peaceful and restful, just perfect. "
United States
Victoria R.
$228 nightly
The price is $258
Dec 11 - Dec 12
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Terrace/patio
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Southeast Yonkers
8.2 out of 10, Very Good, (18)
"Great place great location"
United States
Daquan H.
$115 nightly
The price is $135
Dec 14 - Dec 15
Total with taxes and fees
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
TV, fireplace
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Carmel Hamlet
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
$328 nightly
The price is $355
Dec 15 - Dec 16
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Property grounds
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Waterside
9.8 out of 10, Exceptional, (9)
"Lovely little home in Stamford."
United States
Pat A.
$291 nightly
The price is $329
Dec 14 - Dec 15
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Outdoor dining
45 Minutes from NYC, Entire House near Stamford Downtown,

45 Minutes from NYC, Entire House near Stamford Downtown,

Downtown Stamford
10.0 out of 10, Exceptional, (20)
"Our hosts were very attentive and responsive with communications. The house is lovely, clean, well stocked and in a great location. We thoroughly enjoyed our stay!"
United States
Megan P.
$332 nightly
The price is $376
Dec 17 - Dec 18
Total with taxes and fees
45 Minutes from NYC, Entire House near Stamford Downtown,
Interior
Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!

Highland Falls
10.0 out of 10, Exceptional, (7)
"Convenient location. Nice to have 3 queen beds. One parking space is in a lot, but street for any additional. Plenty of availability though. Excellent washer and dryer, dishwasher. Internet worked well. "
United States
Matt D.
$265 nightly
The price is $297
Dec 10 - Dec 11
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
Fridge, microwave, oven, stovetop
Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!

Highland Falls
9.0 out of 10, Wonderful, (4)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
$302 nightly
The price is $332
Dec 11 - Dec 12
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
Luxury House | Private kitchen | Full-size fridge, microwave, oven, stovetop
Luxury NY Home with Free Parking

Luxury NY Home with Free Parking

4.0 star property
White Plains
8.0 out of 10, Very Good, (1)
"Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine. "
United States
Safiya
$423 nightly
The price is $483
Dec 10 - Dec 11
Total with taxes and fees
Luxury NY Home with Free Parking
Exterior
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
Norwalk
10.0 out of 10, Exceptional, (8)
"We were so pleased with the accommodations. The location is so quiet in a charming neighborhood. The home is well equipped with kitchen supplied and entertainment options. We were delighted to be able to barbecue. Claudia is very responsive and helpful."
Canada
nawab k.
$525 nightly
The price is $594
Jan 5 - Jan 6, 2026
Total with taxes and fees
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Property grounds
Fun, Friends, and Family Lakefront Home w/Dock and Beach

Fun, Friends, and Family Lakefront Home w/Dock and Beach

Mahopac
10.0 out of 10, Exceptional, (12)
"Super convenient location :)"
United States
Sean M.
$666 nightly
The price is $721
Dec 11 - Dec 12
Total with taxes and fees
Fun, Friends, and Family Lakefront Home w/Dock and Beach
Marina
Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach

Cove - East Side - Shippan
10.0 out of 10, Exceptional, (23)
"A very nice house, with excellent service and an unbeatable location. We had a great time."
Mexico
Armando V.
$686 nightly
The price is $729
Dec 11 - Dec 12
Total with taxes and fees
Stylish Beach Home near Stamford Downtown/Beach
Interior
Contemporary Cozy Cottage

Contemporary Cozy Cottage

Lake Peekskill
10.0 out of 10, Exceptional, (30)
"Very clean comfortable quiet place"
United States
Mauro C.
$367 nightly
The price is $420
Dec 10 - Dec 11
Total with taxes and fees
Contemporary Cozy Cottage
Outdoor dining
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

West Side
9.4 out of 10, Exceptional, (6)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
$517 nightly
The price is $559
Dec 15 - Dec 16
Total with taxes and fees
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...
House | 5 bedrooms
Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow

2.0 star property
Ossining
$836 nightly
The price is $932
Jan 5 - Jan 6, 2026
Total with taxes and fees
Foliage at Westchester Manor - Near Sleepy Hollow
Property grounds
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

North Stamford
10.0 out of 10, Exceptional, (105)
"Wonderful family home!Everything you need!Beautiful location!Great host!"
United States
Linda T.
$831 nightly
The price is $941
Dec 14 - Dec 15
Total with taxes and fees
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
TV
Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Cove - East Side - Shippan
9.4 out of 10, Exceptional, (3)
"We chose to stay here for a family event nearby. We found the property very clean and comfortable throughout our stay and would not hesitate to book it again. Although this trip wasn’t about adventuring elsewhere, we know it is convenient to many great places in Fairfield County, Connecticut, as well as New York."
United States
Ellen L.
$480 nightly
The price is $517
Dec 14 - Dec 15
Total with taxes and fees
Spacious 3 Bd Home Pet Friendly, Parking and Laundry
Private kitchen
Aspen In Airmont NY

Aspen In Airmont NY

Airmont
10.0 out of 10, Exceptional, (7)
"We had an excellent stay in this beautiful house. Favorite thing is the magnificent dining table."
United States
Yides W.
Aspen In Airmont NY
Exterior
Cheerful Home in Yonkers NY

Cheerful Home in Yonkers NY

Lincoln Park
7.6 out of 10, Good, (4)
"Nice neighborhood,open concept.Hreat space for my entire family.Kitchen big and spacious. Beds are huge. Definitely will stay here again."
United States
Tanya J.
$490 nightly
The price is $577
Dec 31 - Jan 1, 2026
Total with taxes and fees
Cheerful Home in Yonkers NY
Fridge, microwave, oven, stovetop
Peaceful 5 Bedroom 3 Bathroom House - 30 min from NYC

Peaceful 5 Bedroom 3 Bathroom House - 30 min from NYC

Tuckahoe
9.4 out of 10, Exceptional, (8)
"Lots of sleeping and common space. Super easy to work with the owner."
United States
Dorian L.
$913 nightly
The price is $1,017
Dec 31 - Jan 1, 2026
Total with taxes and fees
Peaceful 5 Bedroom 3 Bathroom House - 30 min from NYC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chappaqua Hotel Reviews

Hyatt Place New York/Yonkers

Hyatt Place New York/Yonkers

10/10 Excellent
"Smooth check-in, very nice , clean room. Excellent location "
donna 1-night trip
Posted 1 day ago
Hyatt Place New York/Yonkers

Find out more about Chappaqua

Chappaqua Vacation Homes information

Number of reviews
274
Accommodation
326 Vacation Homes
Lowest Price
$135
Highest Price
$1,017

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