Chappaqua Vacations from $458

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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.
Delta Hotels by Marriott Woodbridge

Delta Hotels by Marriott Woodbridge

4 out of 5
Save 100% on your flight
Price was $874, price is now $458 per person
$458
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,002 reviews)
Front desk person was very unfriendly and uninterested.

Reviewed on Apr 9, 2026

2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Price was $5,133, price is now $2,304 per person
$2,304
per person
Jun 25 - Jun 29
found 5 hours ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!

Reviewed on Mar 19, 2026

Seven Beach Lane

Seven Beach Lane

2 out of 5
Save 100% on your flight
Price was $1,791, price is now $902 per person
$902
per person
May 18 - May 22
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
10/10 Exceptional! (7 reviews)
Courteous and friendly staff

Reviewed on Nov 4, 2025

Topping Rose House

Topping Rose House

4.5 out of 5
Price was $2,919, price is now $1,582 per person
$1,582
per person
Jun 7 - Jun 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (145 reviews)
Overall it was a great stay! Best part of the cottage was the bathroom with its deep big tub and walk in shower. But the room itself lacked visual appeal & some conveniences usually associated with booking a cottage which is more private and removed from the house. Could use more and better art in the room. I would also trade all the storage space for a mini fridge, tea kettle or coffee maker. Also the only full-size mirror is hidden far back in the bathroom which isn’t terrible but very inconvenient to check the outfit before heading out the door. It’s little odd things that just made it not feel like a luxury stay. And no one mentioned to us beforehand that the sauna, gym, pool area (even though in off season) was under renovation and not available to use. The restaurant was amazing though, room service was wonderful. And staff were adorable. But I don’t know if we would book again tbh.

Reviewed on Mar 24, 2026

Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking

3.5 out of 5
Southeast Yonkers
Price was $3,063, price is now $1,726 per person
$1,726
per person
May 18 - May 22
found 1 day ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
6.4/10 (6 reviews)
This was an excellent House My birthday weekend was amazing I totally would book again

Reviewed on Mar 17, 2024

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Chappaqua Hotel Deals

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $141 total per night from Apr 26 to Apr 27
$141 total
Apr 26 - Apr 27
Total with taxes and fees
8.2/10 Very Good! (1,656 reviews)
Everything was nice

Reviewed on Apr 16, 2026

Baymont by Wyndham White Plains - Elmsford
LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

3 out of 5
3530 Webster Ave Bronx NY
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $135 total per night from Apr 19 to Apr 20
$135 total
Apr 19 - Apr 20
Total with taxes and fees
8.2/10 Very Good! (476 reviews)
Loved the stay just didn’t like the fact your cleaners was slamming the doors early in the morning and you could hear a two people fighting in one of the rooms

Reviewed on Apr 15, 2026

LIV Hotel Bronx - Newly Built
Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

2.5 out of 5
160 Corporate Blvd Yonkers NY
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $144 total per night from Apr 27 to Apr 28
$144 total
Apr 27 - Apr 28
Total with taxes and fees
8.4/10 Very Good! (1,828 reviews)
Good

Reviewed on Apr 16, 2026

Hampton Inn & Suites Yonkers
See all 1,294 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.

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

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Frequently asked questions

How much does a Chappaqua vacation package cost?
You'll find cheap prices from $458 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.

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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.