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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Chappaqua holiday rentals

Luxury Apartment | Private kitchen

1. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is 4.688.480 ₫
9.262.971 ₫ total
includes taxes & fees
21 Aug - 22 Aug
Elegant Hideaway with Free Parking
Villa, Garden View | Living area

2. Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
The price is 5.890.050 ₫
10.637.266 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Luxury NYC Home Game Room Free Parking
Apartment (1 Bedroom) | Interior

3. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is 3.717.276 ₫
7.589.264 ₫ total
includes taxes & fees
24 Aug - 25 Aug
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Luxury Villa, Garden View | Dining

4. Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
2.0 out of 10, (1 review)
"Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere."
United States
Kathleen
The price is 5.890.050 ₫
11.245.904 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Luxury NYC Home with Free Parking for 12
House | 5 bedrooms

5. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is 18.363.124 ₫
32.860.616 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Summer Pool Oasis Custom Bar Arcade Pool Table
Dining

6. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is 5.890.050 ₫
10.460.565 ₫ total
includes taxes & fees
23 Aug - 24 Aug
Prime Luxe 3-BR NYC - Free Parking
Exterior

7. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (162 reviews)
"The front desk gentleman that checked us in was excellent!!"
United States
Selena
The price is 3.518.323 ₫
4.046.072 ₫ total
includes taxes & fees
23 Aug - 24 Aug
Stamford Suites
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

Hyatt Regency Greenwich

Hyatt Regency Greenwich

8/10 Good
"Hotel staff members were all very friendly and polite. The food was great as well. More importantly, the hotel provided a safe environment as we travelled through the area."
Arnold 1-night trip
Posted 9 hours ago
Hyatt Regency Greenwich

Frequently asked questions

Can I find a holiday rental in Chappaqua?

Yes, there are holiday rentals in Chappaqua close to Chappaqua Performing Arts Center, 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.

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 Bruce Museum of Arts and Science, or get out into nature at a spot like Hardscrabble Wilderness Area. Chappaqua Performing Arts 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.