Chappaqua Holiday Rentals

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Holiday Rentals in Chappaqua

Aparthotel in Norwalk

2.5 star property
8.6 out of 10, Excellent, (19)
"Lovely property in a gorgeous setting. Staff were very responsive and welcoming. "
United States
Holly
The price is AU$220
includes taxes & fees
13 Dec - 14 Dec
The Mansion Hotel-style

Apartment in Highland Falls

10.0 out of 10, Exceptional, (13)
"Great Unit."
United States
Rudy R.
The price is AU$410
includes taxes & fees
9 Dec - 10 Dec
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Apartment in Greenwich

3.0 star property
The price is AU$348
includes taxes & fees
9 Dec - 10 Dec
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

Holiday Home in Highland Falls

10.0 out of 10, Exceptional, (2)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
The price is AU$601
includes taxes & fees
9 Dec - 10 Dec
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Holiday Home in Greenwich

9.6 out of 10, Exceptional, (23)
"The property was beautiful and clean, very comfortable with a nice view of the lake! Our hosts were helpful and attentive without being intrusive in any way. Our stay was peaceful and restful, just perfect. "
United States
Victoria R.
The price is AU$372
includes taxes & fees
9 Dec - 10 Dec
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Apartment in Highland Falls

10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is AU$291
includes taxes & fees
15 Dec - 16 Dec
Cozy 1-bedroom retreat minutes from West Point!

Apartment in Croton-on-Hudson

10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
The price is AU$349
includes taxes & fees
9 Dec - 10 Dec
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

Apartment in Croton-on-Hudson

10.0 out of 10, Exceptional, (6)
"We had an excellent stay! Our hosts were kind and helpful. The home was modern and very well kept, very clean. I would highly recommend this location and home to anyone traveling in the area."
United States
Suzanne A.
The price is AU$423
includes taxes & fees
10 Dec - 11 Dec
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

Apartment in CROTON HDSN

9.8 out of 10, Exceptional, (90)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
The price is AU$392
includes taxes & fees
9 Dec - 10 Dec
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Apartment in Carmel Hamlet

9.0 out of 10, Wonderful, (2)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is AU$422
includes taxes & fees
9 Dec - 10 Dec
Charming 1-bedroom apartment in Carmel with WiFi, AC

Apartment in Highland Falls

10.0 out of 10, Exceptional, (5)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
The price is AU$406
includes taxes & fees
9 Dec - 10 Dec
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Apartment in Greenwich

2.0 star property
The price is AU$343
includes taxes & fees
9 Dec - 10 Dec
2 Mi to NYC Train: WFH-Friendly Greenwich Apt!

Apartment in Norwalk

3.0 star property
The price is AU$261
includes taxes & fees
9 Dec - 10 Dec
Gold Coast Getaway! Upscale Apt Near New Canaan

Apartment in Norwalk

2.0 star property
The price is AU$265
includes taxes & fees
9 Dec - 10 Dec
Gold Coast Getaway! Upscale Apt Near New Canaan

Apartment in Getty Square

2.0 star property
The price is AU$535
includes taxes & fees
15 Dec - 16 Dec
Cozy Apartment to Relax - Apartment "A"

Holiday Home in Downtown Stamford

10.0 out of 10, Exceptional, (20)
"Our hosts were very attentive and responsive with communications. The house is lovely, clean, well stocked and in a great location. We thoroughly enjoyed our stay!"
United States
Megan P.
The price is AU$572
includes taxes & fees
17 Dec - 18 Dec
45 Minutes from NYC, Entire House near Stamford Downtown,

Holiday Home in Southeast Yonkers

8.2 out of 10, Very good, (18)
"Great place great location"
United States
Daquan H.
The price is AU$206
includes taxes & fees
10 Dec - 11 Dec
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Apartment in Highland Falls

9.2 out of 10, Wonderful, (9)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is AU$627
includes taxes & fees
10 Dec - 11 Dec
Local Artist Inspired | Walk to WestPoint + King Bed

Apartment in Downtown Stamford

9.6 out of 10, Exceptional, (5)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is AU$555
includes taxes & fees
15 Dec - 16 Dec
Modern Luxe 1BR Apt in Downtown Stamford

Holiday Home in Highland Falls

10.0 out of 10, Exceptional, (5)
The price is AU$628
includes taxes & fees
21 Dec - 22 Dec
House on the Babbling Brook- Quiet 2BR + King Bed!
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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Top Chappaqua Hotel Reviews

Find out more about Chappaqua

Everything you need to know about Chappaqua holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chappaqua holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chappaqua holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chappaqua holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chappaqua. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chappaqua holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chappaqua holiday rentals we have selected for you start as low as AU$206 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chappaqua rentals

At Expedia, we put the best Chappaqua holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chappaqua rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chappaqua holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chappaqua. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Chappaqua?

Yes, there are holiday rentals close to the most popular sights in Chappaqua, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Chappaqua has a good selection of restaurants. Make sure you have time to check out the sporting events and entertainment choices during your trip.

What are some of the best holiday rentals that Chappaqua has to offer?

3BR Prime Luxury near NYC w Arcade Room: This holiday home rental outside of Chappaqua is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals will I find in Chappaqua?

Expedia has 4 holiday rentals for your stay in Chappaqua.

What’s there to see and do in Chappaqua?

Explore the area and family-friendly sights such as Bruce Museum of Arts and Science, or get out into nature at a spot like Hardscrabble Wilderness Area. Thomas J. Watson Research Center and Rockefeller State Park Preserve are a couple of places you'll find in the wider area.

What’s a holiday rental in Chappaqua like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chappaqua. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a small group gathering.