Chappaqua Vacation Packages

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Top Chappaqua Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (8 reviews)
The place and amenities were really nice. The only bad thing was the bathroom got nasty really quick so for me the shared bathrooms won’t work. But they do have private bathroom rooms. Other than the dirty bathrooms not getting cleaned enough everything was great, location and space.

Reviewed on Jun. 25, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,004 reviews)
One of the nicest stays we've stayed And we stay at least in 20-25 hotels a year

Reviewed on Jul. 18, 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (3,398 reviews)
Overall given the chance I would happily go back. I thought it was a great value for the money

Reviewed on Aug. 5, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
This place was amazing, from the bartender Josh to Seiki and Selina, and also JD the concierge, I know I’m leaving people out but the entire staff made our stay perfection, it was first class all the way and I would never stay anywhere else when we go back, just truly a first rate experience

Reviewed on Aug. 3, 2025

The Manner, The Unbound Collection by Hyatt

The Manner, The Unbound Collection by Hyatt

5 out of 5
Manhattan
per person
Oct 25 - Oct 30
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (36 reviews)
The lounge area is super cozy and relaxing.

Reviewed on Aug. 4, 2025

Ready to book your vacation to Chappaqua?

 

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Chappaqua Hotel Deals

Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303, Orangeburg, NY
The price is CA $99 per night from Sep 2 to Sep 3
CA $99
CA $111 total
Sep 2 - Sep 3
includes taxes & fees
6/10 (1,990 reviews)
Nice last-minute booking
"It was your basic last minute motel booking nice enough to spend the night if you have to clean rooms despite the outside of appearance, but don’t make it your first pick restaurant closed bar closed, but on the high side pool is beautiful and open and open late."

Reviewed on Jul. 28, 2025

Armoni Inn & Suites
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Aug 17 to Aug 18
CA $204
CA $233 total
Aug 17 - Aug 18
includes taxes & fees
8.2/10 Very Good! (1,386 reviews)
"Older but well kept property. Very nice staff and the room was wxcellent."

Reviewed on Aug. 3, 2025

Baymont by Wyndham White Plains - Elmsford
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is CA $188 per night from Aug 17 to Aug 18
CA $188
CA $216 total
Aug 17 - Aug 18
includes taxes & fees
7.8/10 Good! (1,094 reviews)
"Everything was great and would tell family and friend to stay"

Reviewed on Aug. 4, 2025

Hampton Inn White Plains/Tarrytown
See all 1,149 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
All Inclusive Vacations
Beach Vacations
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Frequently asked questions

How much does a Chappaqua vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,209 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.