Chappaqua Vacations from $318

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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.
Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Save 100% on your flight
Price was $549, price is now $318 per person
$318
per person
Apr 17 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (6,546 reviews)
Excellent location, friendly staff, and clean rooms. Nothing fancy but was perfect for our stay!

Reviewed on Mar 5, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Price was $1,672, price is now $916 per person
$916
per person
Apr 14 - Apr 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.2/10 Wonderful! (143 reviews)
Everything and everyone was just lovely! Comfortable Welcoming Great restaurant

Reviewed on Feb 22, 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,851, price is now $1,036 per person
$1,036
per person
May 17 - May 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.8/10 Exceptional! (1,411 reviews)
Heat was running, but room was still cold

Reviewed on Mar 4, 2026

Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $762, price is now $438 per person
$438
per person
Apr 17 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,941 reviews)
We enjoyed our five-night stay there. The experience rooms were a bit cozy for four of us, but we made it work. The service was truly wonderful, especially when we received our coffee—they were excellent!

Reviewed on Mar 4, 2026

Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,418, price is now $848 per person
$848
per person
May 17 - May 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (1,751 reviews)
The stay was good, but the wait for

Reviewed on Mar 2, 2026

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Chappaqua Hotel Deals

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
$132 nightly
The price is $151 total per night from Mar 8 to Mar 9
$151 total
Mar 8 - Mar 9
Total with taxes and fees
8.2/10 Very Good! (1,589 reviews)
Safe, quiet, clean and predictable. If you are looking for a place to stay with no drama, comfortable beds, and easy parking then this is a really good spot! I I appreciate how easy it is to access MSK. My only advice is if you’re not feeling well make sure you don’t get a room by the vending machine ...

Reviewed on Mar 4, 2026

Baymont by Wyndham White Plains - Elmsford
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
$106 nightly
The price is $123 total per night from Mar 22 to Mar 23
$123 total
Mar 22 - Mar 23
Total with taxes and fees
9/10 Wonderful! (1,074 reviews)
I’ve stayed here a few times and the front desk staff is always fantastic. The rooms are clean and it is close to restaurants and shopping.

Reviewed on Mar 2, 2026

DoubleTree by Hilton Hotel Nanuet
LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

3 out of 5
3530 Webster Ave Bronx NY
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $137 total per night from Mar 8 to Mar 9
$137 total
Mar 8 - Mar 9
Total with taxes and fees
8.2/10 Very Good! (373 reviews)
Internet was super fast, room was in a good condition, AC /Heater worked fine .

Reviewed on Mar 4, 2026

LIV Hotel Bronx - Newly Built
See all 1,293 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 $318 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.