Chappaqua Vacations from $339

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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.
Topping Rose House

Topping Rose House

4.5 out of 5
Price was $735, price is now $339 per person
$339
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (136 reviews)
Great rooms, staff and food

Reviewed on Sep 28, 2025

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was $787, price is now $418 per person
$418
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (6,546 reviews)
Staff was great! If you're looking for frills and completely updated this isn’t the place for you. If you're looking for a good location than this is perfect. The pictures displayed on the standard room are of the superior, not the standard. The beds were pretty hard, but some may like that.

Reviewed on Feb 3, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $948, price is now $522 per person
$522
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (3,348 reviews)
Clean rooms and space in room.

Reviewed on Feb 2, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was $2,726, price is now $1,502 per person
$1,502
per person
Apr 9 - Apr 14
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
Excellent stay! Friendly staff, comfortable, beautiful rooms & lobby.

Reviewed on Feb 2, 2026

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Chappaqua Hotel Deals

Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
$180 nightly
The price is $206 total per night from Mar 2 to Mar 3
$206 total
Mar 2 - Mar 3
Total with taxes and fees
8.6/10 Excellent! (1,260 reviews)
Very nice room, comfortable bed, spacious and clean. The staff was very friendly and helpful. The food was excellent. I would stay here again.

Reviewed on Jan 30, 2026

Sonesta White Plains Downtown
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4 out of 5
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $118 total per night from Feb 22 to Feb 23
$118 total
Feb 22 - Feb 23
Total with taxes and fees
8.8/10 Excellent! (1,058 reviews)
Thank you to the staff at DoubleTree in Nanuet, NY. Excellent service Clean rooms Respectful staff Great breakfast. Thank you again… 😊

Reviewed on Feb 3, 2026

DoubleTree by Hilton Hotel Nanuet
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $140 total per night from Feb 22 to Feb 23
$140 total
Feb 22 - Feb 23
Total with taxes and fees
8.2/10 Very Good! (1,519 reviews)
Nice and clean room Non smoking

Reviewed on Jan 30, 2026

Baymont by Wyndham White Plains - Elmsford
See all 1,275 properties in Chappaqua
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 $339 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.

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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.