Chappaqua Vacations from $577

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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

Manhattan
Save 100% on your flight
$577
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (7,860 reviews)
The location was perfect for the purpose of our trip as it was only a short walk to the Morgan Library and other attractions we were visiting. The staff was friendly and helpful. The room was basic but clean and the air conditioning worked well. The hotel is older and while it shows some wear & tear it’s not being neglected. We arrived on an early flight and the front desk let us drop our luggage off so we could hit the sites prior to checking in. There aren’t many “amenities” hence the low score for that category but the hotel served our needs for this trip and I wouldn’t mind staying there again.

Reviewed on Aug 31, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

Save 100% on your flight
$1,803
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,005 reviews)
Such a beautiful and magical experience at this hotel . I loved every minute of my stay !

Reviewed on Aug 31, 2026

1 Hotel Central Park

1 Hotel Central Park

Manhattan
Save 100% on your flight
$2,604
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,020 reviews)
The hotel is in a great location but was disappointed in my room. The closet was more like a cupboard and I had to get creative on hanging my clothes. There is no chest for drawers. The lighting switches are confusing but figured them out. Even on the full lighting, the room is dim. The staff was great.

Reviewed on Aug 30, 2026

OYO Times Square

OYO Times Square

Manhattan
Save 100% on your flight
$922
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
6.8/10 (2,083 reviews)
The lobby is lovely, and of course we love Serendipity! For my stay, the Luggage Guy was THE BEST! We were so grateful for the 2;h bag check, as we arrived in NYC at 6am and couldn’t check in until 3pm. The front desk lines were frequently long and slow-moving, and when we were checking in around 4pm they told us there was no hot water, so they’d remove the facility fee if we wanted to stay, though when we went upstairs to our room the hot water was working fine and we didn’t have any trouble with it after 3 showers. I let the front desk know around 8pm that our water worked fine, and they were shocked. So like… whoever is in charge over here is not doing a very good job. I kept coming downstairs to check if the only ice machine was working yet - it said “refilling ice” every time I checked until I gave up at 11pm. It still wasn’t working when we checked out the next day either, and no one at the front desk had any idea how long it would take or how to fix it or even where to buy ice in the area. Our room wouldn’t get cold, so we called down and they said they’d send “the engineer” up but they never showed up. Also the carpet was wet near the bathroom and seemed soapy, but WAY too wet to be from any normal cleaning. The rooms were very quiet though! I didn’t hear anything from adjacent rooms - it seemed like no one was in there, so either that’s true or this hotel actually has decent walls. TBD. We did hear a lot of street noise from Times Square through the windows, which ev

Reviewed on Aug 31, 2026

NobleDEN Hotel

NobleDEN Hotel

Manhattan
Save 100% on your flight
$1,021
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.8/10 Exceptional! (1,662 reviews)
Loved this hotel! Would definitely come back. Staff was very welcoming and room was super cute. Good location close to little Italy and Chinatown. Loved the access to the rooftop.

Reviewed on Aug 29, 2026

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Stay near popular Chappaqua attractions

Chappaqua Performing Arts Center

Enjoy an outing to Chappaqua Performing Arts Center during your stay in Chappaqua. You can enjoy the restaurants while in the area.
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Chappaqua Hotel Deals

Tarrytown House Estate

Tarrytown House Estate

49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$181 nightly
$207 total
Sep 1 - Sep 2
Total with taxes and fees
8.2/10 Very Good! (1,272 reviews)
"The grounds and outside lawns and gardens are beautiful, but the interior seems somewhat old and run down."

Reviewed on Aug 30, 2026

Tarrytown House Estate
Royal Regency Hotel

Royal Regency Hotel

165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
$119 nightly
$140 total
Sep 27 - Sep 28
Total with taxes and fees
8.6/10 Excellent! (2,850 reviews)
"It was a great place to be"

Reviewed on Aug 31, 2026

Royal Regency Hotel
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

200 West Main Street Elmsford NY
Fully refundableReserve now, pay when you stay
$113 nightly
$129 total
Sep 13 - Sep 14
Total with taxes and fees
Hampton Inn White Plains/Tarrytown
See all 1,228 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 $577 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.