Chappaqua Vacations from $574

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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 Wayne Inn

The Wayne Inn

2 out of 5
Save 100% on your flight
Price was $1,130, price is now $574 per person
$574
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
6.8/10 (289 reviews)
Hair dryer was broken and no one came to repair it. There was a roach. The black out curtain was stuck so I couldn't adjust it. The gasket seal on the fridge door was faulty. The sink randomly leaked. The person who checked me in was oddly aggressive just because I didn't want to sign a blank receipt. Telling me I don't know how to check into hotels as if I'm not in my late 30s...

Reviewed on Feb 21, 2026

Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking

2 out of 5
Bryn Mawr
Save 100% on your flight
Price was $7,952, price is now $4,489 per person
$4,489
per person
Jul 18 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to White Plains (HPN)
6.8/10 (3 reviews)
Beautiful layout. Property had everything that was needed for an awesome stay.

Reviewed on Feb 27, 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was $3,769, price is now $2,175 per person
$2,175
per person
Jun 4 - Jun 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,000 reviews)
Just wonderful The staff at the hotel are magnificent Alway consistent always fantastic We will return time and time again! Concierge are the best in the city…

Reviewed on Apr 28, 2026

WestHouse New York

WestHouse New York

5 out of 5
Manhattan
Save 100% on your flight
Price was $1,676, price is now $983 per person
$983
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,005 reviews)
We absolutely enjoyed our stay! The staff were excellent special shout out to Telik and Nick. Beautiful decor. I highly recommend it.

Reviewed on Apr 29, 2026

Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC

4 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $2,335, price is now $1,389 per person
$1,389
per person
Jul 18 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to White Plains (HPN)
2/10 (3 reviews)
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Chappaqua Hotel Deals

Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $101 total per night from May 17 to May 18
$101 total
May 17 - May 18
Total with taxes and fees
6/10 (2,188 reviews)
Basic place. A bit dated. Great for the price. I wish vending machines were working. Helpful staff.

Reviewed on Apr 30, 2026

Armoni Inn & Suites
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
Fully refundable
$127 nightly
The price is $146 total per night from May 31 to Jun 1
$146 total
May 31 - Jun 1
Total with taxes and fees
8.4/10 Very Good! (1,099 reviews)
Parking was a little tough. I do think those big workers trucks were huge which would take some of the next parking spaces. More parking spots should be made available in the future.

Reviewed on Apr 30, 2026

EVEN Hotel Norwalk by IHG
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$177 nightly
The price is $203 total per night from May 7 to May 8
$203 total
May 7 - May 8
Total with taxes and fees
8.2/10 Very Good! (1,047 reviews)
terrible all around

Reviewed on May 1, 2026

Tarrytown House Estate
See all 1,300 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 $574 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.