Chappaqua Vacations from $252

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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.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Price was $540, price is now $252 per person
$252
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
7.4/10 Good! (5,413 reviews)
I loved that it was easy to get to, safe, and friendly.

Reviewed on Nov 28, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $908, price is now $365 per person
$365
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9.2/10 Wonderful! (2,008 reviews)
There were so many broken amenities, hair dryer, sink, remote control and even the key access reader. Staff members were super friendly though, they need some maintenance done.

Reviewed on Nov 26, 2025

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was $637, price is now $297 per person
$297
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
8.6/10 Excellent! (2,613 reviews)
The location was ideal for our stay. The restaurant food was amazing.

Reviewed on Nov 22, 2025

Ultra-Modern Luxe Sleek & Stunning Stay

Ultra-Modern Luxe Sleek & Stunning Stay

2 out of 5
Price was $1,471, price is now $701 per person
$701
per person
Jan 30 - Feb 3
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
2/10 (1 review)
Windrose On Hudson

Windrose On Hudson

3 out of 5
Price was $911, price is now $440 per person
$440
per person
Feb 5 - Feb 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
7.8/10 Good! (80 reviews)
The property was clean & well groomed with lovely grounds. Staff was very accommodating and helpful at checkin. Was surprised that there was no mini fridge in the room. Did not realize there would not be one at booking. Parking was quite far from hotel and it was an uphill walk back. Also did not notice any handicapped parking closer by.

Reviewed on Nov 28, 2025

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Chappaqua Hotel Deals

Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
$176 nightly
The price is $201 total per night from Dec 18 to Dec 19
$201 total
Dec 18 - Dec 19
Total with taxes and fees
8.6/10 Excellent! (1,130 reviews)
Staff was nice; room was clean

Reviewed on Nov 23, 2025

Sonesta White Plains Downtown
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $121 total per night from Dec 1 to Dec 2
$121 total
Dec 1 - Dec 2
Total with taxes and fees
8.2/10 Very Good! (2,392 reviews)
Love the place, staff were very friendly, rooms clean, breakfast so yummy, and my kids love the place.

Reviewed on Nov 24, 2025

Royal Regency Hotel
Ramada by Wyndham Bronx

Ramada by Wyndham Bronx

3 out of 5
1000 Baychester Ave Bronx NY
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $134 total per night from Nov 30 to Dec 1
$134 total
Nov 30 - Dec 1
Total with taxes and fees
8.2/10 Very Good! (1,018 reviews)
Great place

Reviewed on Nov 21, 2025

Ramada by Wyndham Bronx
See all 1,213 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 $252 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.