
Chappaqua Vacations from $361
Book a Hotel + Flight or Car together to unlock savings
Your Chappaqua Vacation
Book a custom vacation package to Chappaqua and get ready to experience this exciting city the way you want. Consider spending time in the neighborhood of Montrose, which is good for walking and tons more. Like to start exploring your surroundings? Sing Sing Correctional Facility, Rockefeller State Park Preserve and Union Church of Pocantico Hills are a few of the top-rated places to visit during a trip to Chappaqua. Whoever you're escaping with and whatever your bank balance, your dream Chappaqua vacation is just a few clicks away with Expedia.
The Latest Chappaqua vacation packages
Price found within the past 48 hours. Click for updated prices.

Windrose On Hudson
Price was $742, price is now $361 per person
$361
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
8.4/10 Very Good! (9 reviews)
Only one night so did not use the amenities. The refrigerator in the room died in the night so lost my leftovers. The room was clean and the staff was helpful. The shower function was strange. I would stay there again.
Reviewed on Aug 12, 2025

The Inn At Fox Hollow Hotel
Price was $705, price is now $362 per person
$362
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful
Reviewed on Aug 12, 2025



Chappaqua Hotel Deals

Hampton Inn White Plains/Tarrytown
200 West Main Street, Elmsford, NY
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $145 total per night from Sep 1 to Sep 2
$145 total
Sep 1 - Sep 2
Total with taxes and fees
7.8/10 Good! (1,128 reviews)
Good hotel but rude guests
"The staff were very nice and helpful. The room could do with a refresh but was clean and comfortable. The noise from the roads outside was loud making sleep harder. The dog barking on one side and the constant arguing on the other side didn't help. More soundproofing would be nice. Breakfast and ..."
Reviewed on Aug 22, 2025

Royal Regency Hotel
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $127 total per night from Sep 7 to Sep 8
$127 total
Sep 7 - Sep 8
Total with taxes and fees
8.2/10 Very Good! (2,216 reviews)
"Room was nice and clean. It’s in residential area right front of private homes. Was bet noisy. Overall I was satisfied. Staff was friendly."
Reviewed on Aug 22, 2025

Amsterdam Hotel
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $116 total per night from Aug 25 to Aug 26
$116 total
Aug 25 - Aug 26
Total with taxes and fees
8.4/10 Very Good! (1,643 reviews)
"Hotel rooms are very big but outdated. Beds were comfortable atleast and close to freeway!"
Reviewed on Aug 23, 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.