Chappaqua Vacations

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Find the Best Chappaqua Vacation Packages

Chappaqua Hotel Deals

Tarrytown House Estate

Tarrytown House Estate

49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
NT$5,093
NT$6,627 total
Aug 23 - Aug 24
includes taxes & fees
8.2/10 Very Good! (1,252 reviews)
"Front desk staff were helpful and the grounds are immaculate. We also had a great experience at Goosefeather, the onsite restaurant. We had 2 beds in our room. One was comfortable. One was springy. The property is older and could’ve been maintained better. Changing of the carpet in general areas ..."

Reviewed on 2026/8/17

Tarrytown House Estate
Royal Regency Hotel

Royal Regency Hotel

165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
NT$3,892
NT$4,743 total
Aug 30 - Aug 31
includes taxes & fees
Royal Regency Hotel
Sonesta White Plains Downtown

Sonesta White Plains Downtown

66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
NT$5,326
NT$7,154 total
Sep 6 - Sep 7
includes taxes & fees
8.8/10 Excellent! (1,359 reviews)
"Loved the location!"

Reviewed on 2026/8/17

Sonesta White Plains Downtown
See all 1,248 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.

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.
See properties

Frequently asked questions

How much does a Chappaqua vacation package cost?
You'll find cheap prices 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?
January, February and November are the best times to search for cheap Chappaqua vacation packages. Traveling in less busy periods means you can usually find reduced prices on accommodations and flights.
How many days is enough for Chappaqua?
Typically, a handful of days is enough to visit the top sights during your Chappaqua vacation. But if you want to have some time to kick back 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.
How to plan a trip to Chappaqua?
  1. Pick your dates: What you want to do in Chappaqua and your preferred season will help you decide when to go.
  2. Figure out your budget: Ensure you have enough money to cover everything from food and transportation to flights and experiences. Your accommodations will likely be the largest expense during your trip to Chappaqua.
  3. Set the duration of your trip: Start by listing all the activities and sights you want to experience in Chappaqua. Then, estimate how long you'll need for each, including any travel time.
  4. Combine your airfare and accommodations: After you've nailed down your trip dates and duration, lock in the right Chappaqua vacation package for you.

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