Chappaqua Vacations from $1,074
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Seven Beach Lane
$1,150
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
9.4/10 Exceptional! (29 reviews)
Property was extremely conveniently located to Main Street. The pool was clean with plenty of towels. Staff was pleasant. Great overall experience.
Reviewed on Aug 11, 2026
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.
Chappaqua Hotel Deals
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$181 nightly
$207 total
Aug 23 - Aug 24
Total with taxes and fees
Royal Regency Hotel
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
$103 nightly
$121 total
Aug 30 - Aug 31
Total with taxes and fees
Sonesta White Plains Downtown
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
$195 nightly
$223 total
Sep 6 - Sep 7
Total with taxes and fees
8.8/10 Excellent! (1,350 reviews)
"Entire facility was amazing. Property was well maintained and very well appointed. Room was clean and spacious. Always ample parking for hotel guests. Would recommend staying to all"
Reviewed on Aug 11, 2026
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
Frequently asked questions
How much does a Chappaqua vacation package cost?
You'll find cheap prices from $1,074 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
- Tibbetts Brook Park
- Metropolitan Museum of Art
- Monroe College New Rochelle Campus
- Orchard Beach
- College of New Rochelle
- Inwood Hill Nature Center
- Flushing Meadows-Corona Park
- American Museum of Natural History
- Sing Sing Correctional Facility
- Empire State Building
- Madison Square Park
- Wall Street
- Castle Gould
- Newyork-Presbyterian Allen Hospital
- Carnegie Hall
- George Washington Bridge Bus Station
- Dobbs Ferry Vacations
- Bronx Park
- Haas Audubon Sanctuary
- 5th Avenue
- Fordham University
- Saint Vladimir's Orthodox Theological Seminary
- Nbc Studios
- Palisades Vacations
- Woodlawn Cemetery
- Bronx Vacations
- Top of the Rock Observation Deck
- Bartow Pell Mansion Museum
- Arthur W. Butler Memorial Sanctuary
- Lehman Center for the Performing Arts
- Yankee Stadium
- Columbus Circle
- Hart Island
- Westchester County Vacations
- Brynwood Golf and Country Club
- Crooked Island Caves
- Bear Mountain State Park
- Chelsea Piers
- Rink at Rockefeller Center
- Bowery Ballroom
- Trump Tower
- Beacon Theater
- Glen Island Park
- Solomon R. Guggenheim Museum
- Hardscrabble Wilderness Area
- Edward J. Murray Memorial Skating Center
- Mount Vernon Vacations
- Hawthorne Vacations
- Empire City Casino
- Edgar Allan Poe Cottage
- Lincoln Center
- New York Vacations
- Armonk Vacations
- New Rochelle Vacations
- New York Botanical Gardens
- Intrepid Sea
- Sleepy Hollow Vacations
- Statue of Liberty
- Eugene and Agnes Meyer Nature Preserve
- Pelham Bay Park
- Hudson River Museum
- Philipse Manor Hall State Historic Site
- Rockefeller State Park Preserve
- Times Square
- Sarah Lawrence College
- College of Mount Saint Vincent
- Yonkers Vacations
- Lenoir Preserve
- Van Cortlandt Park
- Scarsdale Vacations
- Thomas Paine Cottage Museum
- Roberto Clemente State Park
- St. Patrick's Cathedral
- Westchester Hills Cemetery
- Ed Sullivan Theater
- Yonkers Raceway
- Belvedere Castle
- Bay Plaza Shopping Center
- New York Public Library
- Newyork-Presbyterian - Westchester Hospital
- Tuckahoe Vacations
- St. Paul's Church National Historic Site
- Sprain Lake Golf Course
- Everett Children's Adventure Garden
- Purchase Vacations
- Theater District Vacations
- New Roc City
- Mount Kisco Vacations
- Apollo Theater
- Rockland Lake State Park
- Hearst Tower
- Bethesda Fountain
- Cudner-Hyatt House Complex
- Hastings-On-Hudson Vacations
- The Bronx Museum of the Arts
- Science Barge
- Thomas J. Watson Research Center
- Gantry Plaza State Park
- Iona College
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
