Chappaqua Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Chappaqua Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel St. James
Manhattan
$967
per person
Nov 12 - Nov 17
found 7 hours ago
Roundtrip flight included
Raleigh (RDU) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Times Square and Broadway are located nearby.
The location is GREAT! A small fridge in the room would be great, also the ice machine looks like it’s for a kitchen counter. The hotel could implement these small things and the guests would appreciate it! Connollys Irish pub is two doors down, yummy food. I’m DONUTS is a few doors down across the street. Duane Reede /walgreens is across the street as well as a Starbucks that opens at 5am. Close enough to everything but far enough away to rest and relax too! Beds are comfortable.
Reviewed on Oct 5, 2026
1 Hotel Central Park
Manhattan
$1,911
per person
Dec 30 - Jan 3
found 6 hours ago
Roundtrip flight included
Jacksonville (JAX) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions 5th Avenue and Radio City Music Hall are located nearby.
The William Hotel Midtown, New York
Manhattan
$1,289
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Popular attractions Bryant Park and Grand Central Terminal are located nearby.
Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder
Queens
$1,603
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to New York (JFK)
Stay at this aparthotel in Long Island City. Enjoy free WiFi, housekeeping, and air conditioning. Popular attractions Grand Central Terminal and 5th Avenue are located nearby.
I've written my comments before on my experience and what I've eye witnessed - clumps of hair and grime all over the bathroom walls and bathtub, slimy oily floors, scratch groove marks all over the vinyl floor (could not walk bare feet), tiny pillows, not very helpful and slow reservation process and obtaining the door access codes, etc.). It was extremely disappointing.
As a result, I left the hotel room without staying over night. I would not go back here again.
Reviewed on Oct 4, 2026
Park Lane New York
Manhattan
$1,305
per person
Dec 30 - Jan 3
found 6 hours ago
Roundtrip flight included
Jacksonville (JAX) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions 5th Avenue and Rockefeller Center are located nearby.
Terrific hotel with beautiful views of the park!
Reviewed on Oct 4, 2026
The Plaza, A Fairmont Hotel
Manhattan
$3,730
per person
Dec 30 - Jan 3
found 5 hours ago
Roundtrip flight included
Jacksonville (JAX) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions 5th Avenue and Radio City Music Hall are located nearby.
Beautiful hotel with spacious rooms. We never wanted to leave!
Reviewed on Oct 4, 2026
Chappaqua Vacation Packages
Trying to figure out a way to bundle your flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® Chappaqua vacation packages can help. We're here to book everything you'll need to make your Chappaqua trip one to remember. With just a few clicks, you can pick the best vacation package for you and your family. AARP Travel Center has an amazing list of accommodations and flight, and Chappaqua things to do to select from.
Chappaqua Hotels
Our listings include accommodations that are close to all the Chappaqua points of interest, and some that are just outside the city center for a peaceful retreat.
We have great deals on everything from luxury hotels that check off all the vacation must-haves to inexpensive hotels which are great for those on a budget. You can search all the options and pick the hotel that is ideal for you and your family. With AARP Travel Center's Chappaqua hotel packages, you not only get a great rate on your flight, but also a fantastic place to stay.
Things to do in Chappaqua
The fact that you are traveling to Chappaqua means your vacation will already be off to a good start. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.
If you are looking for more, then head over to our "Things to Do" page for more inspiration or to reserve an activity in Chappaqua.
Book Together and Save
With so much to see and do in Chappaqua, you'll be wanting to focus on your outings, not spending time to searching for the cheapest hotel. AARP Travel Center allows you to quickly reserve all you wish for, and save a little money at the same time. You can coordinate your entire vacation, including activities in Chappaqua from just one place. The hardest packing you'll have to do is for your suitcase. Book today and save!
Top Hotel Deals
LIV Hotel Bronx - Newly Built
3530 Webster Ave Bronx NY
Stay at this hotel in Bronx. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Yankee Stadium and Bronx Zoo are located nearby.
Baymont by Wyndham White Plains - Elmsford
540 Saw Mill River Rd Elmsford NY
Book a stay at this business-friendly hotel in Elmsford. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and ...
West Gate Inn Nyack
26 Route 59 Nyack NY
Book a stay at this business-friendly hotel in Nyack. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Armoni Inn & Suites
329 Route 303 Orangeburg NY
Book a stay at this business-friendly hotel in Orangeburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. ...
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Book a stay at this business-friendly hotel in Tarrytown. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful ...
Sleepy Hollow Hotel, a Dolce by Wyndham
455 S Broadway Tarrytown NY
Book a stay at this spa hotel in Tarrytown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
Royal Regency Hotel
165 Tuckahoe Rd Yonkers NY
Book a stay at this business-friendly hotel in Yonkers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant ...
Westchester Marriott
670 White Plains Rd Tarrytown NY
Book a stay at this spa hotel in Tarrytown. Enjoy free parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Royal Hotel Bronx
3362 Boston Road Bronx NY
Stay at this hotel in Bronx. Enjoy free WiFi, a 24-hour front desk, and cable TV channels. Popular attractions Yankee Stadium and Bronx Zoo are located ...
Hilltop Inn & Suites
125 Tuckahoe Rd Yonkers NY
Book a stay at this business-friendly hotel in Yonkers. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Westchester's Ridge Hill and Legoland ...
Hampton Inn White Plains/Tarrytown
200 West Main Street Elmsford NY
Book a stay at this business-friendly hotel in Elmsford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Sonesta White Plains Downtown
66 Hale Ave White Plains NY
Book a stay at this business-friendly hotel in White Plains. Enjoy free WiFi, breakfast (surcharge), and free airport pick-up. Our guests praise the bar and ...
Amsterdam Hotel
19 Clarks Hill Ave Stamford CT
Book a stay at this business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hyatt Regency Greenwich
1800 E Putnam Avenue Old Greenwich CT
Book a stay at this business-friendly hotel in Old Greenwich. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff ...
Overlook Lodge at Bear Mountain
55 Hessian Drive Bear Mountain NY
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sat, Oct 24 - Wed, Oct 28
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$137
Roundtrip
found 4 days ago
Tue, Nov 10 - Wed, Nov 18
DFW
Dallas-Fort Worth Intl.
LGA
LaGuardia
$157
Roundtrip
found 4 days ago
Thu, Dec 3 - Sat, Dec 5
DTW
Detroit Metropolitan Wayne County
LGA
LaGuardia
$159
Roundtrip
found 20 hours ago
Sun, Dec 6 - Tue, Dec 8
DTW
Detroit Metropolitan Wayne County
LGA
LaGuardia
$179
Roundtrip
found 20 hours ago
Wed, Dec 9 - Tue, Dec 15
MCO
Orlando Intl.
LGA
LaGuardia
$199
Roundtrip
found 20 hours ago
Best points of interest in Chappaqua
- Westchester County Center Vacations
- United States Military Academy Vacations
- Bear Mountain State Park Vacations
- The Westchester Mall Vacations
- Sarah Lawrence College Vacations
- Sleepy Hollow Cemetery Vacations
- Empire City Casino Vacations
- Capitol Theatre Vacations
- NewYork-Presbyterian - Westchester Hospital Vacations
- Greenwich Avenue Vacations
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