Chappaqua Vacations from $564

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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 $1,111, price is now $564 per person
$564
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Newark Liberty Intl. Airport (EWR)
6.8/10 (289 reviews)
Clean room - hot shower -

Reviewed on May 5, 2026

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $2,228, price is now $1,194 per person
$1,194
per person
Jul 15 - Jul 22
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
8.6/10 Excellent! (2,532 reviews)
Fun location. Clean, great atmosphere

Reviewed on May 1, 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was $2,525, price is now $1,376 per person
$1,376
per person
Jun 25 - Jun 28
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,001 reviews)
The location is fabulous! And the staff were lovely.

Reviewed on May 5, 2026

3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room

2 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $5,668, price is now $3,261 per person
$3,261
per person
Jun 26 - Jul 1
found 11 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to White Plains (HPN)
8/10 Very Good! (1 review)
Ace Hotel New York

Ace Hotel New York

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,183, price is now $705 per person
$705
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
8/10 Very Good! (1,072 reviews)
It just feels cool to stay there. Also that coffee shop in the lobby, plus the bagel storea round the corner. I got more work done and felt more relaxed than anywhere I've stayed in years.

Reviewed on May 4, 2026

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Chappaqua Hotel Deals

EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
$131 nightly
The price is $151 total per night from May 10 to May 11
$151 total
May 10 - May 11
Total with taxes and fees
8.4/10 Very Good! (1,106 reviews)
Ok

Reviewed on May 3, 2026

EVEN Hotel Norwalk by IHG
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
$100 nightly
The price is $119 total per night from May 10 to May 11
$119 total
May 10 - May 11
Total with taxes and fees
8.2/10 Very Good! (513 reviews)
Clean room air conditioning was great staff was ok

Reviewed on May 6, 2026

LIV Hotel Bronx - Newly Built
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
$157 nightly
The price is $180 total per night from May 17 to May 18
$180 total
May 17 - May 18
Total with taxes and fees
8.2/10 Very Good! (1,060 reviews)
Cool spot, just getting to your room is a hike..

Reviewed on May 4, 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 $564 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.