Chappaqua Vacation Packages

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Top Chappaqua Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $2,272, price is now CA $1,338 per person
CA $1,338
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (244 reviews)
The property was absolutely beautiful- so well decorated! The staff was not only helpful and knowledgeable, but also very kind. If you’re looking for a beautiful luxury property, definitely don’t sleep on this one!

Reviewed on Jul 2, 2026

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was CA $2,820, price is now CA $1,359 per person
CA $1,359
per person
Sep 13 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (2,498 reviews)
I love this place. I always choose to go here, but I have been disappointed the last few times that I’ve gone here. I’ve been given rooms where the AC unit is louder than the street. Preventing you from getting a good nights rest then last night I had to go to New York for an emergency and the AC unit in my room was not working and they said they provided a portable little did. I know it was a portable little fan that was blowing hot air I had to take two showers to stay cool and not hyperventilate now wasn’t terribly hot, but I am a person that runs really hot so I need cold AC air and I paid close to $500 on top of that I didn’t even get keys to my room. The maintenance man had to let me in my room. I guess their computer system was on now. The host was nice and kind but very disappointed very disappointed lately.

Reviewed on Jul 13, 2026

2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Price was CA $3,141, price is now CA $1,868 per person
CA $1,868
per person
Aug 31 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to New York (JFK)
6/10 (2 reviews)
Wrong address no instructions

Reviewed on Jun 18, 2026

Faena New York

Faena New York

5 out of 5
Manhattan
Price was CA $3,518, price is now CA $2,163 per person
CA $2,163
per person
Aug 31 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to New York (JFK)
9.6/10 Exceptional! (63 reviews)
Amazing service

Reviewed on Jul 5, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,792, price is now CA $2,982 per person
CA $2,982
per person
Aug 15 - Aug 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Fabulous experience. Front desk staff was extremely helpful, friendly, and efficient. Especially while checking-in. Would come back again! Rooms are thoughtfully designed and have amazing views!

Reviewed on Jul 5, 2026

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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
The price is CA $108 per night from Jul 15 to Jul 16
CA $108
CA $120 total
Jul 15 - Jul 16
includes taxes & fees
6/10 (2,297 reviews)
"The people that were working during my stay were very unprofessional. I called ahead for an 1 hr to say I would be running late no one answered after I call like 3 times I had to go 30 minutes to the hotel just to check myself in and complain that no one answered that I had to come all the way there ..."

Reviewed on Jul 13, 2026

Armoni Inn & Suites
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
The price is CA $263 per night from Jul 16 to Jul 17
CA $263
CA $348 total
Jul 16 - Jul 17
includes taxes & fees
8.8/10 Excellent! (1,332 reviews)
"The Sonesta felt like a mirage in a desert only it was actually real. During what was one of the worst weeks of my life the Sonesta provided solid comfort to help me get through. The staff (from the front desk, the bar, room service) was friendly, empathetic and so very helpful. Forever grateful- ..."

Reviewed on Jul 13, 2026

Sonesta White Plains Downtown
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 $175 per night from Aug 2 to Aug 3
CA $175
CA $252 total
Aug 2 - Aug 3
includes taxes & fees
8.2/10 Very good! (1,170 reviews)
"Amazing property but the restaurant wasn’t what I would liked."

Reviewed on Jul 13, 2026

Tarrytown House Estate
See all 1,267 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.
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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 $1,338 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.

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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.