Chappaqua Holiday Rentals

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Our top choices for Chappaqua holiday rentals

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (15 reviews)
"Great Unit."
United States
Rudy R.
The price is HK$585
HK$2,011 total
includes taxes & fees
19 Jan - 20 Jan
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is HK$729
HK$1,487 total
includes taxes & fees
2 Feb - 3 Feb
Cozy 1-bedroom retreat minutes from West Point!

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is HK$710
HK$2,680 total
includes taxes & fees
16 Jan - 17 Jan
House on the Babbling Brook- Quiet 2BR + King Bed!

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is HK$741
HK$3,126 total
includes taxes & fees
21 Jan - 22 Jan
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.2 out of 10, Wonderful, (10 reviews)
"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 HK$608
HK$2,787 total
includes taxes & fees
20 Jan - 21 Jan
Local Artist Inspired | Walk to WestPoint + King Bed

The Hideaway

The Hideaway
Brewster
10.0 out of 10, Exceptional, (6 reviews)
"Me and my family stayed here for a quick get-away out of the city. Very pretty location, and loved our stay here! Thanks!"
United States
Rick C.
The price is HK$1,209
HK$2,468 total
includes taxes & fees
16 Jan - 17 Jan
The Hideaway

Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
The price is HK$772
HK$2,025 total
includes taxes & fees
18 Jan - 19 Jan
Luxury 1BR located in Prime Yonkers Area

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is HK$780
HK$2,054 total
includes taxes & fees
26 Jan - 27 Jan
Elegant Hideaway with Free Parking

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is HK$1,053
HK$2,163 total
includes taxes & fees
16 Jan - 17 Jan
Charming 1-bedroom apartment in Carmel with WiFi, AC

Cozy secret apartment with free parking in Yonkers

Cozy secret apartment with free parking in Yonkers
Northwest Yonkers
9.8 out of 10, Exceptional, (15 reviews)
"As described. Clean, responsive, great location, great communication. Staying again when avaliable!"
United States
Robert E.
The price is HK$975
HK$2,277 total
includes taxes & fees
16 Jan - 17 Jan
Cozy secret apartment with free parking in Yonkers

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (2 reviews)
"Great stay!"
United States
Ann S.
The price is HK$761
HK$1,834 total
includes taxes & fees
20 Jan - 21 Jan
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
The price is HK$1,224
HK$2,477 total
includes taxes & fees
16 Jan - 17 Jan
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (90 reviews)
"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 HK$820
HK$2,071 total
includes taxes & fees
20 Jan - 21 Jan
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
The price is HK$1,552
HK$2,508 total
includes taxes & fees
19 Jan - 20 Jan
Spacious 3BR Luxe Escape near NYC

Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
Bryn Mawr
The price is HK$858
HK$2,121 total
includes taxes & fees
25 Jan - 26 Jan
Luxe 1BR Oasis - Prime NY Stay

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.6 out of 10, Exceptional, (25 reviews)
"The hosts were very friendly and very accommodating. "
United States
Daniel C.
The price is HK$1,000
HK$2,078 total
includes taxes & fees
23 Jan - 24 Jan
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (12 reviews)
"Absolutely perfect location--so lovely to walk to restaurants, ice cream, views, etc. Would definitely stay here again."
United States
joelle a.
The price is HK$936
HK$1,641 total
includes taxes & fees
4 Feb - 5 Feb
Piermont Oasis

Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is HK$1,187
HK$2,396 total
includes taxes & fees
18 Jan - 19 Jan
Lovely 3BR Home with parking-Walk to WP Gate!

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
8.2 out of 10, Very good, (18 reviews)
"Great place great location"
United States
Daquan H.
The price is HK$737
HK$1,051 total
includes taxes & fees
18 Jan - 19 Jan
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
The price is HK$1,170
HK$2,548 total
includes taxes & fees
18 Jan - 19 Jan
Uscale 2BR Escape in the Heart of NYC
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

Search for holiday rentals in Chappaqua on Expedia! You can easily find your home rentals, villas, holiday apartments in Chappaqua using one of the methods below:

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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?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This holiday home rental outside of Chappaqua is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals will I find in Chappaqua?

Expedia has 3 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 Grand Prix New York / Spins Bowl, or get out into nature at a spot like Hardscrabble Wilderness Area. Thomas J. Watson Research Center and Teatown Lake Reservation 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.