Chappaqua Vacations from $545
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.
Lotte New York Palace
Manhattan
$1,137
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,167 reviews)
Poor customer service, I received no friendly response from any staff. Really disappointed has nothing to do with the NY Palace I used to stay decades ago. Won’t stay again.
Reviewed on Aug 7, 2026
The Towers at Lotte New York Palace
Manhattan
$3,472
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (689 reviews)
We had a wonderful stay, very friendly and helpful staff. Great service. Will come back soon
Reviewed on Aug 8, 2026
Stay near popular Chappaqua attractions
Chappaqua Performing Arts Center
Enjoy an outing to Chappaqua Performing Arts Center during your stay in Chappaqua. You can enjoy the restaurants while in the area.
Chappaqua Hotel Deals
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$181 nightly
$207 total
Aug 10 - Aug 11
Total with taxes and fees
8.2/10 Very Good! (1,223 reviews)
"Expedia listed this as having an adult only outdoor pool. This was not only incorrect but a child had an ‘accident’ in the pool on our second day there which caused the pool to be shut down for the day. The adult pool was the only reason we booked this place. The room smelled so musty that we had ..."
Reviewed on Aug 7, 2026
Royal Regency Hotel
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
$108 nightly
$127 total
Aug 30 - Aug 31
Total with taxes and fees
8.6/10 Excellent! (2,809 reviews)
"The hotel was good. Toilets are low flow so you must flush more than 3x at moments."
Reviewed on Aug 8, 2026
Sonesta White Plains Downtown
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
$188 nightly
$215 total
Aug 30 - Aug 31
Total with taxes and fees
8.8/10 Excellent! (1,340 reviews)
"Awesome"
Reviewed on Aug 8, 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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Frequently asked questions
How much does a Chappaqua vacation package cost?
You'll find cheap prices from $545 on Expedia for your Chappaqua getaway. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Chappaqua costs.
What are the cheapest months to go to Chappaqua?
May, August and December are great times to search for cheap Chappaqua vacation packages. Opting to travel in quieter periods means you can generally find lower prices on hotels and flights.
How many days is enough for Chappaqua?
Usually, a handful of days is enough to check out the top sights during your Chappaqua vacation. But if you want to have time to chill out or go on day trips, think about extending your itinerary.
How to find the best Chappaqua package deals?
Bagging a cheap Chappaqua package deal is a breeze with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget, apply some filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Chappaqua package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Chappaqua vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging hotels and flights individually. Better still, you can customize your Chappaqua escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Chappaqua?
Secure amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Chappaqua escape.
Does Expedia offer Book Now, Pay Later Chappaqua vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Chappaqua trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
Explore a world of travel with Expedia
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- Metropolitan Museum of Art
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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.