Chappaqua Vacations from $495
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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
- INNSiDE by Meliá New York Nomad
Jan 20 - Jan 25INNSiDE by Meliá New York Nomad + Flight
Manhattan5 nights4.5 star property9.2/10 - Wonderful (2,374 reviews)"Had a great time"Reviewed November 8, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - EWR • Nonstop EWR - ATL • Nonstop$961$495found 1 day agoper traveler - Hotel Riu Plaza New York Times Square
Jan 10 - Jan 16Hotel Riu Plaza New York Times Square + Flight
Manhattan6 nights4.0 star property9.0/10 - Wonderful (3,464 reviews)"My second time staying here and it never disappoints. Very clean, comfortable and attentive staff."Reviewed November 9, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - JFK • Nonstop JFK - ATL • Nonstop - JW Marriott Essex House New York
Jan 20 - Jan 24JW Marriott Essex House New York + Flight
Manhattan4 nights4.5 star property8.8/10 - Excellent (1,000 reviews)Roundtrip • Atlanta (ATL) - New York (JFK)ATL - JFK • Nonstop JFK - ATL • Nonstop$1,529$888found 1 day agoper traveler - 1 Hotel Brooklyn Bridge
Jan 22 - Jan 241 Hotel Brooklyn Bridge + Flight
Brooklyn2 nights5.0 star property9.2/10 - Wonderful (1,002 reviews)"Incredible views, ambiance, staff, and overall experience! The only thing to note is that it can be quite loud since you're right on the waterfront and the ferries and boats sound their horns frequently"Reviewed November 8, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - LGA • Nonstop EWR - ATL • Nonstop$1,083$636found 10 hours agoper traveler - Hotel Riu Plaza Manhattan Times Square
Jan 20 - Jan 25Hotel Riu Plaza Manhattan Times Square + Flight
Manhattan5 nights4.0 star property9.2/10 - Wonderful (4,162 reviews)"I liked hotel a lot, breakfast was very good and well organized and rooms were big enough. I only didn`t like the door between my room and next room because you can hear next door guests ( talking, tv...)."Reviewed November 9, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - EWR • Nonstop EWR - ATL • Nonstop$967$569found 1 day agoper traveler
Where to stay near Chappaqua
Pleasantville
Discover Pleasantville, a charming destination perfectly suited for families and weekend getaway travelers who will appreciate its vibrant arts scene and outdoor experiences. With attractions like the Westchester County Center for live performances, the historic Van Cortlandt Manor, and the beautiful Rockefeller State Park Preserve, Pleasantville invites exploration and relaxation. Located about 2 miles by car from Chappaqua, it offers easy access to these highlights, making it a smart choice for your next hotel booking.
Millwood
Experience the charm of Millwood, an excellent hub for family travelers and nature enthusiasts eager to explore attractions like the historic Van Cortlandt Manor and the Westchester County Center, known for its music concerts and theater. Enjoy the serene landscapes of nearby parks and nature reserves, perfect for outdoor adventures. Located about 4 miles by car from Chappaqua, Millwood offers a smart choice for your stay, combining accessibility with a rich array of activities.
Thornwood
If you are a family traveler or someone looking for a weekend getaway, Thornwood offers a perfect retreat just about 3 miles away from Chappaqua. This charming city features attractions such as the historic Lyndhurst Mansion, the vibrant Westchester County Center for arts and events, and the beautiful Rockefeller State Park Preserve for outdoor adventures. With a variety of entertainment and shopping options nearby, Thornwood makes for a smart choice to enhance your stay and explore this picturesque region.
Armonk
Armonk stands out as a prime spot for travelers interested in a blend of outdoor activities and city experiences. This charming city offers easy access to attractions like the Westchester County Center and Purchase College, while also providing delightful shopping along Greenwich Avenue. Located about 3 miles by car from Chappaqua, Armonk is an ideal choice for a weekend getaway or family vacation. With its inviting atmosphere and diverse activities, booking a stay in Armonk promises a memorable escape.
Mount Kisco
Looking for the perfect spot? Mount Kisco is ideal for travelers seeking a blend of outdoor adventure and urban experiences, featuring attractions like the historic Van Cortlandt Manor and the vibrant Westchester County Center. Families and weekend getaway seekers will appreciate the nearby beach and lake, making it easy to unwind. Located about 4 miles by car from Chappaqua, Mount Kisco offers a diverse range of activities, making it a smart choice for your vacation stay.
Chappaqua Hotel Deals
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG"Front desk staff was phenomenal! Very personable! Made the first impression a wonderful one."
Baymont by Wyndham White Plains - Elmsford
Baymont by Wyndham White Plains - Elmsford"The property isn't that bad, but the rooms, or at least the one I had, had a terrible smell in the blankets and the carpet. The first girl who checked me in wasn't friendly at all, although I must admit that the girl who checked me out was the complete opposite, the breakfast was okay.. But I think they need to pay more attention to the cleanliness of the rooms"
"Good location to Tarrytown and NY Thruway"
Hampton Inn White Plains/Tarrytown
Hampton Inn White Plains/Tarrytown"Room clean/ comfortable. Easy parking. Breakfast good."
Days Inn by Wyndham Elmsford / White Plains
Days Inn by Wyndham Elmsford / White Plains
Frequently Asked Questions
How much does a Chappaqua vacation package cost?
You'll find cheap prices from $495 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.