Chappaqua Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Chappaqua Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $1,313, price is now CA $857 per person
CA $857
per person
Jan 27 - Jan 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (3,435 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $2,463, price is now CA $1,371 per person
CA $1,371
per person
Jan 15 - Jan 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (293 reviews)

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $5,338, price is now CA $3,053 per person
CA $3,053
per person
Dec 23 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $2,269, price is now CA $1,385 per person
CA $1,385
per person
Jan 13 - Jan 16
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $2,000, price is now CA $1,302 per person
CA $1,302
per person
Jan 8 - Jan 14
found 1 day ago
Roundtrip flight included
Calgary (YYC) to New York (JFK)
9.2/10 Wonderful! (1,000 reviews)
Clean and comfortable

Reviewed on Nov 2, 2026

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Chappaqua Hotel Deals

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
The price is CA $165 per night from Nov 29 to Nov 30
CA $165
CA $194 total
Nov 29 - Nov 30
includes taxes & fees
LIV Hotel Bronx - Newly Built
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Nov 8 to Nov 9
CA $159
CA $194 total
Nov 8 - Nov 9
includes taxes & fees
Royal Regency Hotel
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
The price is CA $278 per night from Nov 11 to Nov 12
CA $278
CA $353 total
Nov 11 - Nov 12
includes taxes & fees
8.2/10 Very good! (1,421 reviews)
"Beautiful estate, family and pet friendly. Rooms are a bit older but totally fine for us. Hotel staff were great. We went in early November, the Fall foliage is beautiful in the Hudson Valley and historic Tarrytown area. Magical stay!"

Reviewed on Nov 3, 2026

Tarrytown House Estate
See all 1,272 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.
All Inclusive Vacations
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Stay near popular Chappaqua attractions

Chappaqua Performing Arts Center

Enjoy an outing to Chappaqua Performing Arts Center during your stay in Chappaqua. You can enjoy the restaurants while in the area.
See properties

Frequently asked questions

How much does a Chappaqua vacation package cost?
You can pick up a vacation package to this popular destination from CA $857 on Expedia. However, how much your vacation to Chappaqua costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Chappaqua?
You can usually find lower prices and greater availability in January, February and November. Check out our cheap Chappaqua vacation packages and you could land some great off-season deals.
How many days is enough for Chappaqua?
With a well-organized schedule, you can easily tick off the main Chappaqua attractions in a few days. But if you prefer to explore off the beaten track or go on day tours, consider booking your Chappaqua vacation for longer.
How to find the best Chappaqua package deals?
Use Expedia's filters to find some great Chappaqua package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Chappaqua package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Chappaqua vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and hotels individually. Better still, you can personalize your Chappaqua escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Chappaqua?
Enjoy incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Chappaqua break.
How to plan a trip to Chappaqua?

  1. Choose when to go: Check your calendar and pack your bags. Your preferred time of year and the available activities will also help you decide when to visit Chappaqua.
  2. Set a budget: Consider expenses like transportation, flights and meals when calculating how much to save for your trip to Chappaqua. Then, pick a property that suits your budget, whether that's an affordable stay or a more luxurious retreat.
  3. Decide how long to go for: Now that you know more about Chappaqua, you can work out the perfect length of your break. Put together a draft plan and give yourself enough time to cover everything you want to do.
  4. Bundle your airfare and accommodations: After you've nailed down your travel dates and duration, book the ideal Chappaqua vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.