Chappaqua Vacations from $392

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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.
Delta Hotels by Marriott Woodbridge

Delta Hotels by Marriott Woodbridge

4 out of 5
Price was $808, price is now $392 per person
$392
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,002 reviews)
Front desk person was very unfriendly and uninterested.

Reviewed on Apr 9, 2026

CODA Williamsburg

CODA Williamsburg

4 out of 5
Price was $1,484, price is now $776 per person
$776
per person
May 30 - Jun 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (474 reviews)
Location location location, I am not a local , I visit new yor k all th time I live in Connecticut. A nice staycation place , close to all nice restaurants, shops and night life too. Local foods a, spirits and vintage stores near by. Great boutique hotel

Reviewed on Apr 10, 2026

Seven Beach Lane

Seven Beach Lane

2 out of 5
Save 100% on your flight
Price was $2,018, price is now $1,117 per person
$1,117
per person
Jun 1 - Jun 3
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (6 reviews)
Courteous and friendly staff

Reviewed on Nov 4, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $3,668, price is now $2,102 per person
$2,102
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,003 reviews)
The hotel is well kept and clean. Easy access to the DUMBO neighborhood, but also the rest of the city. Uber and Lyft are readily available. The hotel staff is very courteous and prompt to respond to issues. My wife greatly enjoyed our stay and will be glad to use this when we are in Brooklyn again.

Reviewed on Apr 12, 2026

Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking

2 out of 5
Bryn Mawr
Save 100% on your flight
Price was $2,525, price is now $1,508 per person
$1,508
per person
May 31 - Jun 3
found 1 day ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
9/10 Wonderful! (2 reviews)
Beautiful layout. Property had everything that was needed for an awesome stay.

Reviewed on Feb 27, 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
$123 nightly
The price is $141 total per night from Apr 26 to Apr 27
$141 total
Apr 26 - Apr 27
Total with taxes and fees
8.2/10 Very Good! (1,656 reviews)
The hours of the pool was inconvenient They should open on the weekends in the morning too so the guests can used before going out of the day

Reviewed on Apr 13, 2026

Baymont by Wyndham White Plains - Elmsford
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 Apr 15 to Apr 16
$137 total
Apr 15 - Apr 16
Total with taxes and fees
7.2/10 Good! (608 reviews)
I had a good stay. For parking You have to come early.

Reviewed on Apr 13, 2026

LIV Hotel Bronx - Newly Built
Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

2.5 out of 5
160 Corporate Blvd Yonkers NY
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $144 total per night from Apr 27 to Apr 28
$144 total
Apr 27 - Apr 28
Total with taxes and fees
8.4/10 Very Good! (1,827 reviews)
great staff,Brian,clean amenities, good breakfast,ice machines were not functional for two nights but fixed on third day,staff gave us ice from somewhere

Reviewed on Apr 13, 2026

Hampton Inn & Suites Yonkers
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 $392 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.