Default HTG hotel image

Search Holiday Rentals in Chappaqua

  • 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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Chappaqua holiday rentals

House (5 Bedrooms) | Interior

1. Nyc-area Escape Near River, Trails & Mta!

Nyc-area Escape Near River, Trails & Mta!
3.0 star property
Ossining
Nyc-area Escape Near River, Trails & Mta!
House | 5 bedrooms

2. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is Rp11.701.522
Rp21.901.013 total
includes taxes & fees
21 Sept - 22 Sept
Summer Pool Oasis Custom Bar Arcade Pool Table
Villa, Garden View | Living area

3. 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 Rp8.790.210
Rp12.699.744 total
includes taxes & fees
27 Sept - 28 Sept
Luxury NYC Home Game Room Free Parking
Luxury Apartment | Private kitchen

4. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
2.0 out of 10, (1 review)
The price is Rp3.180.458
Rp6.283.591 total
includes taxes & fees
22 Sept - 23 Sept
Elegant Hideaway with Free Parking
Dining

5. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is Rp9.589.320
Rp13.326.047 total
includes taxes & fees
21 Sept - 22 Sept
Prime Luxe 3-BR NYC - Free Parking
Exterior

6. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (179 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is Rp2.997.550
Rp3.447.183 total
includes taxes & fees
27 Sept - 28 Sept
Stamford Suites
Luxury Apartment | In-room dining

7. 3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
The price is Rp15.982.200
Rp20.446.118 total
includes taxes & fees
21 Sept - 22 Sept
3BR Prime Luxury NY - Free Parking
Luxury Villa, Garden View | Dining

8. 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 Rp7.191.990
Rp11.188.761 total
includes taxes & fees
24 Sept - 25 Sept
Luxury NYC Home with Free Parking for 12
Luxury Villa, Patio | Living area

9. Luxury 5 BR Home Free Parking

Luxury 5 BR Home Free Parking
2.0 star property
Bryn Mawr
2.0 out of 10, (1 review)
The price is Rp10.388.430
Rp14.267.998 total
includes taxes & fees
21 Sept - 22 Sept
Luxury 5 BR Home Free Parking
Luxury House | Living area

10. Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is Rp15.183.090
Rp19.632.024 total
includes taxes & fees
21 Sept - 22 Sept
Two Wash
Apartment (1 Bedroom) | Interior

11. 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 Rp5.842.382
Rp8.967.080 total
includes taxes & fees
16 Oct - 17 Oct
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Luxury Apartment | Living area

12. Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
Bryn Mawr
2.0 out of 10, (2 reviews)
"My experience did not match the listing. I was asked to make payment outside the platform and the check-in process was not clear. I would not recommend this property. ⸻ ⭐⭐ Balanced Review The property did not meet expectations. When I arrived, the check-in process was unclear and the home appeared to be partially occupied. I was also instructed to make a payment outside of Hotels.com instead of using the platform. This caused confusion and concern. I would suggest the listing be...
United States
Dianelly
The price is Rp5.577.788
Rp8.886.091 total
includes taxes & fees
21 Sept - 22 Sept
Luxe 1BR Oasis - Prime NY Stay
House | Living area

13. Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
5.0 out of 10, (12 reviews)
"Though the privous occupants refused to vacate the property in time but the landlord was suupportive went out of their way and provided a refund option and an alternative...we took the alternative which happen to be better than the originally booked property ... Will use this management and property owner in our upcoming short terms rentals....."
United States
abdelwahab
The price is Rp10.654.800
Rp14.565.999 total
includes taxes & fees
21 Sept - 22 Sept
Modern Luxury Home w GameRoom & Parking
Standard Room, 1 King Bed, Main Building | Property entrance

14. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is Rp6.375.122
Rp7.331.391 total
includes taxes & fees
21 Sept - 22 Sept
Guesthouse at Norwalk Inn
Luxury Apartment | Living area

15. Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
The price is Rp6.428.520
Rp9.837.848 total
includes taxes & fees
30 Sept - 1 Oct
Luxury 3 BR Near NYC with Easy Parking
Luxury House, Garden View | Living area

16. Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
4.8 out of 10, (5 reviews)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is Rp5.020.009
Rp8.262.077 total
includes taxes & fees
2 Oct - 3 Oct
Luxury 3BR Family Home Game Room Parking
Luxury Duplex | Living area

17. Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
9.0 out of 10, Wonderful, (2 reviews)
"The house was very clean and the areas was quiet too. We had a nice spot to park the car. The staff was calling and checking on me if I didn’t have any issues with the check in. They were available all the time. The only thing we will need next time if possible is the washer and dryer and extra towels because we were 5 and only got 3 towels. But overall we enjoyed the stays."
United States
Adj Fatou
The price is Rp5.577.788
Rp9.063.672 total
includes taxes & fees
2 Oct - 3 Oct
Uscale 2BR Escape in the Heart of NYC
Luxury House | Living area

18. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
7.0 out of 10, Good, (4 reviews)
"My family and I were satisfy with the stay I’ll definitely coming back"
United States
Josephine
The price is Rp7.191.990
Rp10.691.980 total
includes taxes & fees
2 Oct - 3 Oct
Spacious 3BR Luxe Escape near NYC
Luxury Apartment | Living area

19. Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
4.8 out of 10, (6 reviews)
"Everything was clean, good communication.. I would like to come back again for sure "
United States
Genesis
The price is Rp5.737.610
Rp9.064.895 total
includes taxes & fees
2 Oct - 3 Oct
Luxury 1BR located in Prime Yonkers Area
Luxury House, Garden View | Dining

20. Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC
4.0 star property
Southeast Yonkers
3.6 out of 10, (4 reviews)
"We never got to stay because THERE WAS ANOTHER FAMILY THERE. THAT WOMEN SAID SHE WAS RENTING THE HOUSE FOR ANOTHER MONTH. "
United States
Angel
The price is Rp7.191.990
Rp10.691.982 total
includes taxes & fees
11 Oct - 12 Oct
Modern Comfort 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.
View all properties
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

Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

10/10 Excellent
"Quiet rooms ( 2nd time here). We had fun in the pool and having drinks lounging by the pool. Staff is pleasant and answers questions well"
Paula 2-night trip
Posted less than an hour ago
Hotel Nyack, a JdV by Hyatt Hotel

Find out more about Chappaqua

Search for holiday rentals in Chappaqua on Expedia.co.id! 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 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.

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

Modern Luxury Home w GameRoom & Parking: This holiday home rental outside Chappaqua is situated near the airport, and has a rooftop terrace and free WiFi to help you feel content during your stay. It has 3 bedrooms, as well as a kitchen with a full-sized fridge, a dishwasher and a stovetop, so that you can cook with friends or family.

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 Hudson Hills Golf Course 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.