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Our top choices for Chappaqua vacation homes

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (5)
"A clean and convenient place to stay for visiting our cadet at West Point. Our hosts were very communicative and helpful. The home and parking situation was just as described. Nice quiet neighborhood, well maintained home. Hearing the babbling broom outside the living room window was very relaxing. Plan on staying here again!"
United States
Maria L.
$335 nightly
The price is $353
Dec 24 - Dec 25
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!

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
Jan 5 - Jan 6, 2026
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
7.6 out of 10, Good, (5)
"Wonderful stay! The property is within walking distance of the little downtown area & had driveway parking. It was clean & plenty spacious. Property owners had great communication! This is a property with 2 units, but we were not bothered by any extra noise. "
United States
Waylon J.
$338 nightly
The price is $382
Dec 25 - Dec 26
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed

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

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.6 out of 10, Exceptional, (23)
"The hosts were very friendly and very accommodating. "
United States
Daniel C.
$215 nightly
The price is $243
Jan 15 - Jan 16, 2026
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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.
$313 nightly
The price is $345
Jan 7 - Jan 8, 2026
Total with taxes and fees
Fabulous 3bdrm Home w/parking!

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, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
$366 nightly
The price is $371
Dec 24 - Dec 25
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !

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)
"Fantastic place. We had a great stay!"
United States
Sara C.
$313 nightly
The price is $354
Jan 8 - Jan 9, 2026
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

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.
$125 nightly
The price is $147
Jan 8 - Jan 9, 2026
Total with taxes and fees
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

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)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
$331 nightly
The price is $376
Jan 7 - Jan 8, 2026
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!

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, (21)
"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.
$371 nightly
The price is $420
Jan 5 - Jan 6, 2026
Total with taxes and fees
45 Minutes from NYC, Entire House near Stamford Downtown,

Fantastic bedroom with AC & fireplace in home in charming Mount Vernon

Fantastic bedroom with AC & fireplace in home in charming Mount Vernon
South Side
$119 nightly
The price is $133
Dec 28 - Dec 29
Total with taxes and fees
Fantastic bedroom with AC & fireplace in home in charming Mount Vernon

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
Historic District
10.0 out of 10, Exceptional, (9)
"Stayed with our adult children for a family wedding. Everyone enjoyed the spotless, attractive & appointed home with lovely king beds in all the rooms. It was a treat!Host was very attentive, would highly recommend!"
United States
Nancy B.
$482 nightly
The price is $546
Jan 19 - Jan 20, 2026
Total with taxes and fees
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Peaceful Palette: 35 mins to NYC

Peaceful Palette: 35 mins to NYC
Hartsdale
10.0 out of 10, Exceptional, (1)
"The house is clean, organized and well stocked for our family’s week-long stay."
United States
Wei D.
$460 nightly
The price is $526
Jan 14 - Jan 15, 2026
Total with taxes and fees
Peaceful Palette: 35 mins to NYC

3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room
2.0 star property
Southeast Yonkers
8.0 out of 10, Very Good, (1)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
United States
Anonymous traveler
$337 nightly
The price is $378
Jan 12 - Jan 13, 2026
Total with taxes and fees
3BR Prime Luxury near NYC w Arcade Room

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 29 - Dec 30
Total with taxes and fees
Contemporary Cozy Cottage

Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
Ossining
$806 nightly
The price is $898
Jan 5 - Jan 6, 2026
Total with taxes and fees
Foliage at Westchester Manor - Near Sleepy Hollow

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.
$714 nightly
The price is $774
Jan 12 - Jan 13, 2026
Total with taxes and fees
Fun, Friends, and Family Lakefront Home w/Dock and Beach

New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (22)
"Great stay!"
United States
Kyra S.
$1,292 nightly
The price is $1,371
Jan 1 - Jan 2, 2026
Total with taxes and fees
New Beach Home near Stamford Downtown/Shippan

Norwalk/Darien Border, 60 Min to NYC, Fire pit

Norwalk/Darien Border, 60 Min to NYC, Fire pit
West Norwalk
$484 nightly
The price is $484
Jan 22 - Jan 23, 2026
Total with taxes and fees
Norwalk/Darien Border, 60 Min to NYC, Fire pit

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.
$520 nightly
The price is $562
Jan 4 - Jan 5, 2026
Total with taxes and fees
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...
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

Find out more about Chappaqua

Chappaqua Vacation Homes information

Number of reviews
180
Accommodation
326 Vacation Homes
Lowest Price
$133
Highest Price
$1,371

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