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.
Modern Comfort in the Heart of NYC
Southeast Yonkers
CA $1,143
per person
Nov 11 - Nov 15
found 15 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to White Plains (HPN)
3.6/10 (4 reviews)
It took calling the booking website customer service to get in contact with the host. I end up getting a different property that the one I reserved but the new on was more bedrooms, at the end I work out but it took some long coy with the host.
Reviewed on Jun 29, 2026
Ready to book your vacation to Chappaqua?
Chappaqua Hotel Deals
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
CA $221
CA $287 total
Aug 30 - Aug 31
includes taxes & fees
8.2/10 Very good! (1,260 reviews)
"I was kept awake by people above me. Heavy walking I wouldn’t recommend staying on a lower level. The building is old and probably contribute to being disturbed by it"
Reviewed on Aug 27, 2026
Royal Regency Hotel
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
CA $167
CA $203 total
Sep 27 - Sep 28
includes taxes & fees
8.6/10 Excellent! (2,839 reviews)
"It was good for the most part but the staff were absolutely horrible specifically this one man at the front desk who treated me and my partner very poorly and didn’t seem welcoming at all"
Reviewed on Aug 27, 2026
Sonesta White Plains Downtown
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
CA $236
CA $316 total
Sep 27 - Sep 28
includes taxes & fees
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 $1,019 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.
