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Chappaqua Vacations from $419

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The Latest Chappaqua Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Meeting facility
    Oct 14 - Oct 17

    Radio Hotel + Flight

    Manhattan
    3 nights
    4.0 star property
    8.6/10 - Excellent (2,495 reviews)
    "Execllent"
    Reviewed August 5, 2026
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - LGA • Nonstop LGA - ATL • Nonstop
    Save 100% on your flight
    $776
    $419
    per traveler
    found 1 day ago
    Radio Hotel
  • Lobby lounge
    Sep 24 - Sep 27

    The Wall Street Hotel + Flight

    Manhattan
    3 nights
    5.0 star property
    9.6/10 - Exceptional (737 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - LGA • Nonstop LGA - ATL • Nonstop
    Save 100% on your flight
    $2,192
    $1,214
    per traveler
    found 1 day ago
    The Wall Street Hotel
  • Front of property
    Oct 11 - Oct 16

    Hotel Riu Plaza New York Times Square + Flight

    Manhattan
    5 nights
    4.0 star property
    9.0/10 - Wonderful (3,269 reviews)
    "The only issue with the room...of the bathroom light was on, you could see the person in the shower...the full silhouette at least. Breakfast was great as it was included with our rate. The cost was a tad higher than I wanted to pay at over $500 for 1 night, but the experience and location were wonderful."
    Reviewed August 5, 2026
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - JFK • Nonstop JFK - ATL • Nonstop
    Save 100% on your flight
    $2,441
    $1,381
    per traveler
    found 1 day ago
    Hotel Riu Plaza New York Times Square
  • Breakfast served
    Oct 11 - Oct 16

    Hotel Riu Plaza Manhattan Times Square + Flight

    Manhattan
    5 nights
    4.0 star property
    9.2/10 - Wonderful (3,849 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - JFK • Nonstop JFK - ATL • Nonstop
    Save 100% on your flight
    $2,165
    $1,243
    per traveler
    found 1 day ago
    Hotel Riu Plaza Manhattan Times Square
  • Room, 1 King Bed (City View or Courtyard View) | In-room safe, desk, blackout drapes, soundproofing
    Sep 6 - Sep 11

    NobleDEN Hotel + Flight

    Manhattan
    5 nights
    4.0 star property
    9.8/10 - Exceptional (1,635 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - JFK • Nonstop JFK - ATL • Nonstop
    Save 100% on your flight
    $1,870
    $1,113
    per traveler
    found 1 day ago
    NobleDEN Hotel

Chappaqua Hotel Deals

Free daily self-serve breakfast

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
2.5 star property
6.7 mi from Chappaqua
8.4 out of 10, Very Good, (1,784 reviews)
$127 nightly
The price is $145
Aug 23 - Aug 24
Total with taxes and fees
Baymont by Wyndham White Plains - Elmsford
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.
See all properties in Chappaqua

Frequently Asked Questions

How much does a Chappaqua vacation package cost?

You'll find cheap prices from $419 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.