
Chappaqua Vacations from $373
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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.

The Inn At Fox Hollow Hotel
Price was $720, price is now $373 per person
$373
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful
Reviewed on Aug 12, 2025

1 Hotel Brooklyn Bridge
Price was $2,261, price is now $1,234 per person
$1,234
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,008 reviews)
Rooms are so nice and spacious. Plenty of room to enjoy indoor time. Lots of outdoor options on and near the property. Highly recommend. Beautiful views of the bridges and the city.
Reviewed on Aug 19, 2025

Sound View Greenport
Save 100% on your flight
Price was $1,358, price is now $752 per person
$752
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (548 reviews)
Our luxury 2 bedroom suite was very nice, clean, and spacious. We had a huge balcony with a view of the Long Island sound
Reviewed on Aug 18, 2025

Windrose On Hudson
Save 100% on your flight
Price was $950, price is now $536 per person
$536
per person
Oct 28 - Nov 1
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (NYC)
8.4/10 Very Good! (8 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 Harbor Front Inn
Save 100% on your flight
Price was $1,042, price is now $589 per person
$589
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (495 reviews)
Great hotel. Staff were amazing! Loved that you could use their sister property by the beach and stay in town. Just did not like having to pay for overnight parking.
Reviewed on Aug 14, 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 includes taxes and fees
7.8/10 Good! (1,123 reviews)
"Pool not in service. Concrete around pool and walk to parking lot in poor shape. Excellent breakfast and well staffed"
Reviewed on Aug 19, 2025

Royal Regency Hotel
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $133 total per night from Sep 1 to Sep 2
$133 total
Sep 1 - Sep 2
Total includes taxes and fees
8.2/10 Very Good! (2,216 reviews)
"Great Room. Hotel is close to the mall and the freeway. We definitely return."
Reviewed on Aug 18, 2025

Norwalk Inn & Conference Center
99 East Avenue, Norwalk, CT
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $144 total per night from Aug 24 to Aug 25
$144 total
Aug 24 - Aug 25
Total includes taxes and fees
8.6/10 Excellent! (1,294 reviews)
"Great value for the money"
Reviewed on Aug 18, 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.