Chappaqua Vacations from $538

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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.
Holiday Inn Express New York City Times Square by IHG

Holiday Inn Express New York City Times Square by IHG

3 out of 5
Manhattan
Save 100% on your flight
Price was $892, price is now $538 per person
$538
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
7.6/10 Good! (2,226 reviews)
wonderful staff wonderful breakfast

Reviewed on Feb 26, 2026

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,207, price is now $704 per person
$704
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (6,546 reviews)
The Hotel St. James was awesome and very reasonable for our 3 night stay! It's right around the corner from the subway in Times Square. The room was very clean and spacious for 2. There are NO amenities (self-serve ice machine in lobby) but that's OK because you can get coffee right across the street and check out Conolly's Pub (very good) just a few doors down along with a convenient store right there as well. The Hotel St. James is an older hotel with character. Definitely recommend and will book my next stay here!

Reviewed on Mar 1, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,528, price is now $1,551 per person
$1,551
per person
Apr 22 - Apr 25
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
Very amazing place, everything is picture worthy.

Reviewed on Feb 21, 2026

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,434, price is now $900 per person
$900
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,723 reviews)
Such a beautiful place. Everyone is friendly and efficient.

Reviewed on Mar 1, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,224, price is now $777 per person
$777
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,001 reviews)
Great location - expensive for your return.

Reviewed on Feb 16, 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
$131 nightly
The price is $150 total per night from Mar 8 to Mar 9
$150 total
Mar 8 - Mar 9
Total with taxes and fees
8.2/10 Very Good! (1,581 reviews)
Very nice and clean great staff

Reviewed on Mar 1, 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! (1,072 reviews)
Everyone was nice. The room was bigger than expected. The room wasn’t warm enough and would blow cold air instead of hot. I didn’t complain or ask for another room because I was honestly too exhausted to complain or move. Outside of that it was lovely and we would stay again. Maybe just not in the ...

Reviewed on Mar 1, 2026

DoubleTree by Hilton Hotel Nanuet
LIV Hotel Bronx

LIV Hotel Bronx

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 3 to Mar 4
$137 total
Mar 3 - Mar 4
Total with taxes and fees
8.2/10 Very Good! (370 reviews)
The room only had one nightstand. Stains on towels. The soap wasn't fresh, it had an old soap smell, like its been there forever. Staff was okay.

Reviewed on Mar 1, 2026

LIV Hotel Bronx
See all 1,279 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 $538 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.