Chappaqua Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday Rentals in Chappaqua

Private kitchen
The Mansion Hotel-style

Aparthotel in Norwalk

2.5 star property
8.4 out of 10, Very good, (15)
"Lovely property in a gorgeous setting. Staff were very responsive and welcoming. "
United States
Holly
The price is HK$683
HK$786 total
includes taxes & fees
2 Dec - 3 Dec
The Mansion Hotel-style
Lobby
Stamford Suites

Aparthotel in Downtown Stamford

4.0 star property
6.2 out of 10, (76)
"It was great"
United States
Natalie
The price is HK$932
HK$1,072 total
includes taxes & fees
7 Dec - 8 Dec
Stamford Suites
Fridge, oven, stovetop, cookware/dishes/utensils
Cozy 1-bedroom retreat minutes from West Point!

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 HK$728
HK$1,485 total
includes taxes & fees
1 Dec - 2 Dec
Cozy 1-bedroom retreat minutes from West Point!
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

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 HK$926
HK$3,334 total
includes taxes & fees
2 Dec - 3 Dec
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Property grounds
Piermont Oasis

Apartment in Piermont

9.8 out of 10, Exceptional, (9)
"Carolyn was so amazing with her directions on how to park and check in. The apartment had everything as advertised. The ambiance was very private and peaceful. Walking distance to the town and pier. I would definitely stay again."
United States
Anonymous traveller
Piermont Oasis
Property entrance
Guesthouse at Norwalk Inn

Aparthotel in Norwalk

3.5 star property
8.4 out of 10, Very good, (40)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is HK$1,880
HK$2,163 total
includes taxes & fees
14 Dec - 15 Dec
Guesthouse at Norwalk Inn
Exterior
House on the Babbling Brook- Quiet 2BR + King Bed!

Holiday Home in Highland Falls

10.0 out of 10, Exceptional, (5)
The price is HK$779
HK$2,781 total
includes taxes & fees
1 Dec - 2 Dec
House on the Babbling Brook- Quiet 2BR + King Bed!
Exterior
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

Apartment in Croton-on-Hudson

10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
The price is HK$768
HK$1,841 total
includes taxes & fees
2 Dec - 3 Dec
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Interior
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

Apartment in Greenwich

3.0 star property
The price is HK$740
HK$1,798 total
includes taxes & fees
3 Dec - 4 Dec
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Exterior detail
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Apartment in Highland Falls

10.0 out of 10, Exceptional, (13)
"Great Unit."
United States
Rudy R.
The price is HK$701
HK$2,062 total
includes taxes & fees
1 Dec - 2 Dec
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Property grounds
3BR West Point Retreat-3min to Back Gate+ King Bed

Holiday Home in Highland Falls

9.0 out of 10, Wonderful, (4)
"Excellent host, house is very clean. The queen and king beds are comfortable. The sound of the brook is relaxing. "
United States
Penny D.
The price is HK$856
HK$3,382 total
includes taxes & fees
1 Dec - 2 Dec
3BR West Point Retreat-3min to Back Gate+ King Bed
Marina
Seabreeze at the beach west beach Stamford ct.

Apartment in Cove - East Side - Shippan

9.8 out of 10, Exceptional, (9)
"Very comfortable and clean units. Outdoor area is great. Very nice neighborhood to walk around and right near a great bar. Appreciated the extras like beach towels, sunscreen, shampoo and laundry soap."
United States
Tom C.
The price is HK$1,142
HK$2,983 total
includes taxes & fees
1 Dec - 2 Dec
Seabreeze at the beach west beach Stamford ct.
Fridge, microwave, oven, stovetop
Cozy Apartment to Relax - Apartment "A"

Apartment in Getty Square

2.0 star property
The price is HK$1,090
HK$2,769 total
includes taxes & fees
7 Dec - 8 Dec
Cozy Apartment to Relax - Apartment "A"
1 bedroom, WiFi, bed sheets
Charming 1-bedroom apartment in Carmel with WiFi, AC

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 HK$1,051
HK$2,168 total
includes taxes & fees
1 Dec - 2 Dec
Charming 1-bedroom apartment in Carmel with WiFi, AC
Marina
Stylish Beach Home near Stamford Downtown/Beach

Holiday Home in Cove - East Side - Shippan

10.0 out of 10, Exceptional, (23)
"A very nice house, with excellent service and an unbeatable location. We had a great time."
Mexico
Armando V.
The price is HK$2,328
HK$5,734 total
includes taxes & fees
1 Dec - 2 Dec
Stylish Beach Home near Stamford Downtown/Beach
Fridge, microwave, oven, stovetop
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

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 HK$1,157
HK$2,119 total
includes taxes & fees
1 Dec - 2 Dec
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Holiday Home in Greenwich

9.6 out of 10, Exceptional, (21)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
The price is HK$876
HK$1,941 total
includes taxes & fees
7 Dec - 8 Dec
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Games room
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

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 HK$835
HK$2,057 total
includes taxes & fees
1 Dec - 2 Dec
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
Interior
Gold Coast Getaway! Upscale Apt Near New Canaan

Apartment in Norwalk

3.0 star property
The price is HK$950
HK$1,350 total
includes taxes & fees
9 Dec - 10 Dec
Gold Coast Getaway! Upscale Apt Near New Canaan
Property grounds
The Hideaway

Apartment in Brewster

10.0 out of 10, Exceptional, (6)
"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$1,207
HK$2,464 total
includes taxes & fees
1 Dec - 2 Dec
The Hideaway
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chappaqua Hotel Reviews

Amsterdam Hotel

Amsterdam Hotel

10/10 Excellent
"No complaints whatsoever and will always return to this hotel whenever I come back!😊"
GODFREY 9-night trip
Posted 3 days ago
Amsterdam Hotel

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:

  • View our selection of featured holiday rentals in Chappaqua
  • Use the map to find apartments and other holiday homes in the Chappaqua neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chappaqua while they last

Look no further and take a look at our great range of rental properties in Chappaqua!

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.