Chappaqua Vacations from $638
Book a Hotel + Flight or Car together to unlock savings
The Latest Chappaqua Vacation Packages
- Radio Hotel
Sep 18 - Sep 21Radio Hotel + Flight
Manhattan3 nights4.0 star property8.6/10 - Excellent (2,493 reviews)Roundtrip • Atlanta (ATL) - New York (JFK)ATL - JFK • Nonstop JFK - ATL • Nonstop - NobleDEN Hotel
Oct 20 - Oct 25NobleDEN Hotel + Flight
Manhattan5 nights4.0 star property9.8/10 - Exceptional (1,634 reviews)"We loved the NobleDEN! Best location, walkable to everywhere, room had nice view over Grand Street. Would definitely stay again."Reviewed August 2, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - LGA • Nonstop EWR - ATL • Nonstop - 33 Hotel, New York City, Seaport
Oct 20 - Oct 2533 Hotel, New York City, Seaport + Flight
Manhattan5 nights5.0 star property9.2/10 - Wonderful (1,005 reviews)Roundtrip • Atlanta (ATL) - New York (JFK)ATL - LGA • Nonstop EWR - ATL • Nonstop - Library Hotel by Library Hotel Collection
Oct 14 - Oct 17Library Hotel by Library Hotel Collection + Flight
Manhattan3 nights4.0 star property9.6/10 - Exceptional (1,004 reviews)"Having worked in libraries when I was young and volunteered in a Nica library when I was old the name drew me to the hotel but also that it was on Madison Ave right by Bryant Park. Very cool without being hipster, yeah which means the hotel had a closet with plenty of hangers, drawers, the right amenities in addition to a great location, fantastic staff and yes lots of shelves with books. One floor not only had books but a piano with lots of drinks and snacks but also was opened 24/7. The..."Reviewed August 3, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - EWR • Nonstop EWR - ATL • Nonstop - Hotel Riu Plaza Manhattan Times Square
Oct 10 - Oct 14Hotel Riu Plaza Manhattan Times Square + Flight
Manhattan4 nights4.0 star property9.2/10 - Wonderful (3,845 reviews)"Toilet is shaped weird. But other than that beautiful hotel. Staff was friendly. The lobby is nice to just sit in. Literally right next to all the sights. I went for Broadway and that was less than 5 mins. Would definitely stay again. Just be aware of the traffic outside of the hotel. In the day time they only allow specific drivers and deliveries."Reviewed August 4, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - LGA • Nonstop EWR - ATL • Nonstop
Frequently Asked Questions
How much does a Chappaqua vacation package cost?
You'll find cheap prices from $638 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.