Chappaqua Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Chappaqua Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway
Manhattan
CA $1,015
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (3,714 reviews)
Finding my room and the elevators was difficult each time. The room was sparse, but surprisingly very clean.
The lobby is busy and chaotic; the big slope at the front door needs a warning sign.
Reviewed on Oct 14, 2026
Margaritaville Resort Times Square
Manhattan
CA $1,502
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (4,269 reviews)
I was on vacation in New York City, location was excellent, Staff was friendly, Room was very small, yet it was perfect, plenty of storage for a week's worth of clothes for 2 people. Beds were comfortable. Bathroom had good counter space, shower head could use some maintenance. It didn't hold in place. Overall very happy with my stay
Reviewed on Oct 14, 2026
Ready to book your vacation to Chappaqua?
Chappaqua Hotel Deals
LIV Hotel Bronx - Newly Built
3530 Webster Ave Bronx NY
Fully refundableReserve now, pay when you stay
CA $199
CA $234 total
Nov 3 - Nov 4
includes taxes & fees
Baymont by Wyndham White Plains - Elmsford
540 Saw Mill River Rd Elmsford NY
CA $192
CA $220 total
Nov 4 - Nov 5
includes taxes & fees
8.4/10 Very good! (1,890 reviews)
"It was very clean. Bed was comfortable. Elevators had issues. The pool water was not as warm as others described. Overall the stay was good. I would stay there again."
Reviewed on Oct 12, 2026
West Gate Inn Nyack
26 Route 59 Nyack NY
CA $139
CA $159 total
Nov 11 - Nov 12
includes taxes & fees
7.4/10 Good! (1,476 reviews)
"bedding wasn’t clean. Fridge was loud and interrupted sleep."
Reviewed on Oct 14, 2026
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.
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.
Frequently asked questions
How much does a Chappaqua vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,015 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?
- 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.
- 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.
- 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.
- 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.
