Chappaqua Vacations from $303

Book a Hotel + Flight or Car together to unlock savings

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.
The Mansion at Glen Cove

The Mansion at Glen Cove

4 out of 5
Price was $514, price is now $303 per person
$303
per person
Jan 22 - Jan 25
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
7/10 Good! (1,001 reviews)
What I did not like, bathroom setup. One hook by the shower, no hooks by the sink for hand towels. No shelf in the shower for any bath products, everything has to be put on the floor of the shower. Shower fixtures not easy to switch, overall experience very dissatisfing.

Reviewed on Oct 26, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $786, price is now $414 per person
$414
per person
Jan 15 - Jan 19
just found
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Stayed in for one night and the room was beautiful. The bed was beyond comfortable and clean. From the check in to check out, staff was very helpful. 100% will recommend.

Reviewed on Oct 25, 2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,511, price is now $864 per person
$864
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.8/10 Good! (1,593 reviews)
Room wasn't ready 1.5 hours after the states check in time. The hotel is used for a lot of other purposes for such a small space so it's awkward to shimmy through someone's bat mitzvah to get up to our rooms. We heard really loud tribal drumming from tao when we were up on the 2nd floor. The best things are pretty decent sized rooms for NYC and awesome location.

Reviewed on Oct 20, 2025

Hotel 48LEX New York

Hotel 48LEX New York

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,592, price is now $927 per person
$927
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.2/10 Very Good! (1,010 reviews)
The room was very clean and I had house keeping come and refresh everything daily. The dish washer was a tad bit dirty but it's New York so we ate out a lot and didn't need to was dishes so it didn't interfere with our stay. Overall this hotel hit every box for us! Definitely our new ho to spot!

Reviewed on Oct 25, 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was $1,368, price is now $800 per person
$800
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,008 reviews)
Poor front desk service.

Reviewed on Oct 27, 2025

Don't see what you're looking for?
See all available trips from Columbus to Chappaqua
View all trips

Chappaqua Hotel Deals

Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303, Orangeburg, NY
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $109 total per night from Oct 30 to Oct 31
$109 total
Oct 30 - Oct 31
Total with taxes and fees
6/10 (2,148 reviews)
The room was terrific, clean and comfortable upon my arrival. Parking was fine, but there is no lighted "Armoni Inn" sign off Rt. 303 so guests know where to turn at night. Staff was quite courteous and helpful, although the staffer at the front desk wasn't able to break a $20 bill so I could tip ...

Reviewed on Oct 27, 2025

Armoni Inn & Suites
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $129 total per night from Nov 23 to Nov 24
$129 total
Nov 23 - Nov 24
Total with taxes and fees
8.2/10 Very Good! (2,335 reviews)
I love this place.

Reviewed on Oct 27, 2025

Royal Regency Hotel
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
$138 nightly
The price is $157 total per night from Nov 16 to Nov 17
$157 total
Nov 16 - Nov 17
Total with taxes and fees
8.2/10 Very Good! (1,425 reviews)
The staff was very friendly.

Reviewed on Oct 17, 2025

Baymont by Wyndham White Plains - Elmsford
See all 1,203 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chappaqua vacation package cost?
You'll find cheap prices from $303 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.