Chappaqua Vacations from $311

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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.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Price was $698, price is now $311 per person
$311
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.4/10 Good! (5,413 reviews)
Convenient and great location. Wish the rooms were updated.

Reviewed on Dec 11, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $787, price is now $349 per person
$349
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
Instead of a small bottle of wine. Room upgrade is better

Reviewed on Dec 12, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $854, price is now $433 per person
$433
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Electric charging in back

Reviewed on Dec 9, 2025

CODA Williamsburg

CODA Williamsburg

4 out of 5
Save 100% on your flight
Price was $952, price is now $498 per person
$498
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.2/10 Very Good! (402 reviews)
Hate to give it 3 stars. Staff was excellent and accommodating, great location. However, there was a lot of noise at night making it difficult to sleep and woke us early in the morning. For some reason There was a storage closet beside our room door and could hear staff after 10pm.

Reviewed on Dec 5, 2025

Hyatt Union Square New York

Hyatt Union Square New York

4 out of 5
Manhattan
Save 100% on your flight
Price was $858, price is now $458 per person
$458
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.6/10 Excellent! (1,001 reviews)
The staff is terrific! The hotel is in a great location, and the rooms are quiet, clean, and comfortable.

Reviewed on Nov 30, 2025

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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 Jan 1 to Jan 2
$141 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.2/10 Very Good! (1,460 reviews)
Comfortable and clean. In a good location off the highway and near the bridge. Great price for location!

Reviewed on Dec 1, 2025

Baymont by Wyndham White Plains - Elmsford
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
$195 nightly
The price is $223 total per night from Dec 27 to Dec 28
$223 total
Dec 27 - Dec 28
Total with taxes and fees
8.6/10 Excellent! (1,144 reviews)
The hotel is beautiful. The staff is friendly, courteous and goes above & beyond to assist in any way possible.

Reviewed on Dec 7, 2025

Sonesta White Plains Downtown
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $116 total per night from Dec 18 to Dec 19
$116 total
Dec 18 - Dec 19
Total with taxes and fees
8.2/10 Very Good! (2,394 reviews)
Breakfast was OK and the staff friendly.

Reviewed on Dec 6, 2025

Royal Regency Hotel
See all 1,218 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 $311 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.