Chappaqua Vacations from $373

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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.
The Inn At Fox Hollow Hotel
1 Hotel Brooklyn Bridge
Sound View Greenport
Windrose On Hudson
The Harbor Front Inn
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Chappaqua Hotel Deals

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street, Elmsford, NY
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $145 total per night from Sep 1 to Sep 2
$145 total
Sep 1 - Sep 2
Total includes taxes and fees
7.8/10 Good! (1,123 reviews)
"Pool not in service. Concrete around pool and walk to parking lot in poor shape. Excellent breakfast and well staffed"

Reviewed on Aug 19, 2025

Hampton Inn White Plains/Tarrytown
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $133 total per night from Sep 1 to Sep 2
$133 total
Sep 1 - Sep 2
Total includes taxes and fees
8.2/10 Very Good! (2,216 reviews)
"Great Room. Hotel is close to the mall and the freeway. We definitely return."

Reviewed on Aug 18, 2025

Royal Regency Hotel
Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue, Norwalk, CT
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $144 total per night from Aug 24 to Aug 25
$144 total
Aug 24 - Aug 25
Total includes taxes and fees
8.6/10 Excellent! (1,294 reviews)
"Great value for the money"

Reviewed on Aug 18, 2025

Norwalk Inn & Conference Center
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.

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Frequently asked questions

How much does a Chappaqua vacation package cost?
You'll find cheap prices from $373 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.