
Chappaqua Vacations from $574
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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 Wayne Inn
Save 100% on your flight
Price was $1,130, price is now $574 per person
$574
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
6.8/10 (289 reviews)
Hair dryer was broken and no one came to repair it. There was a roach. The black out curtain was stuck so I couldn't adjust it. The gasket seal on the fridge door was faulty.
The sink randomly leaked.
The person who checked me in was oddly aggressive just because I didn't want to sign a blank receipt. Telling me I don't know how to check into hotels as if I'm not in my late 30s...
Reviewed on Feb 21, 2026

Luxury 3BR Family Home Game Room Parking
Bryn Mawr
Save 100% on your flight
Price was $7,952, price is now $4,489 per person
$4,489
per person
Jul 18 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to White Plains (HPN)
6.8/10 (3 reviews)
Beautiful layout. Property had everything that was needed for an awesome stay.
Reviewed on Feb 27, 2026

Loews Regency New York Hotel
Manhattan
Save 100% on your flight
Price was $3,769, price is now $2,175 per person
$2,175
per person
Jun 4 - Jun 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,000 reviews)
Just wonderful
The staff at the hotel are magnificent
Alway consistent always fantastic
We will return time and time again!
Concierge are the best in the city…
Reviewed on Apr 28, 2026

WestHouse New York
Manhattan
Save 100% on your flight
Price was $1,676, price is now $983 per person
$983
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,005 reviews)
We absolutely enjoyed our stay! The staff were excellent special shout out to Telik and Nick. Beautiful decor. I highly recommend it.
Reviewed on Apr 29, 2026

Chappaqua Hotel Deals

Armoni Inn & Suites
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $101 total per night from May 17 to May 18
$101 total
May 17 - May 18
Total with taxes and fees
6/10 (2,188 reviews)
Basic place. A bit dated. Great for the price. I wish vending machines were working. Helpful staff.
Reviewed on Apr 30, 2026

EVEN Hotel Norwalk by IHG
426 Main Ave, Route 7 Norwalk CT
Fully refundable
$127 nightly
The price is $146 total per night from May 31 to Jun 1
$146 total
May 31 - Jun 1
Total with taxes and fees
8.4/10 Very Good! (1,099 reviews)
Parking was a little tough. I do think those big workers trucks were huge which would take some of the next parking spaces. More parking spots should be made available in the future.
Reviewed on Apr 30, 2026

Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$177 nightly
The price is $203 total per night from May 7 to May 8
$203 total
May 7 - May 8
Total with taxes and fees
8.2/10 Very Good! (1,047 reviews)
terrible all around
Reviewed on May 1, 2026
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.
Find the Best Chappaqua Vacation Packages
Chappaqua Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | LaGuardia Airport (LGA) |
Population | 1,450 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Capitol Theatre, Franklin D. Roosevelt State Park and Paramount Hudson Valley Theater |
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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.



















