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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)
$335 nightly
The price is $353
Dec 24 - Dec 25
Total with taxes and fees

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)
$328 nightly
The price is $355
Jan 5 - Jan 6, 2026
Total with taxes and fees

3BR West Point Retreat-3min to Back Gate+ King Bed
3BR West Point Retreat-3min to Back Gate+ King BedHighland Falls
7.6 out of 10, Good, (5)
$338 nightly
The price is $382
Dec 25 - Dec 26
Total with taxes and fees

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)
$215 nightly
The price is $243
Jan 15 - Jan 16, 2026
Total with taxes and fees

Fabulous 3bdrm Home w/parking!
Fabulous 3bdrm Home w/parking!Highland Falls
9.0 out of 10, Wonderful, (4)
$313 nightly
The price is $345
Jan 7 - Jan 8, 2026
Total with taxes and fees

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)
$366 nightly
The price is $371
Dec 24 - Dec 25
Total with taxes and fees

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, WiFiWaterside
9.8 out of 10, Exceptional, (9)
$313 nightly
The price is $354
Jan 8 - Jan 9, 2026
Total with taxes and fees

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Nice Cozy Room By Empire City Casino And Cross County Shopping CenterSoutheast Yonkers
8.2 out of 10, Very Good, (18)
$125 nightly
The price is $147
Jan 8 - Jan 9, 2026
Total with taxes and fees
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.
Top Chappaqua Hotel Reviews

Ardsley Acres Hotel Westchester
10/10 Excellent
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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