Default HTG hotel image

Chappaqua Vacation Rentals

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

Our top choices for Chappaqua vacation 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 ￥103,375
￥193,480 total
includes taxes & fees
Sep 21 - Sep 22
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 ￥77,656
￥112,194 total
includes taxes & fees
Sep 27 - Sep 28
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 ￥28,097
￥55,512 total
includes taxes & fees
Sep 22 - Sep 23
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 ￥84,715
￥117,726 total
includes taxes & fees
Sep 21 - Sep 22
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 ￥26,481
￥30,453 total
includes taxes & fees
Sep 27 - Sep 28
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 ￥141,192
￥180,627 total
includes taxes & fees
Sep 21 - Sep 22
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 ￥63,536
￥98,847 total
includes taxes & fees
Sep 24 - Sep 25
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 ￥91,775
￥126,048 total
includes taxes & fees
Sep 21 - Sep 22
Luxury 5 BR Home Free Parking
Luxury House | Living area

10. Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is ￥134,132
￥173,436 total
includes taxes & fees
Sep 21 - Sep 22
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 ￥51,614
￥79,219 total
includes taxes & fees
Sep 30 - Oct 1
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 ￥49,276
￥78,504 total
includes taxes & fees
Sep 21 - Sep 22
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 ￥94,128
￥128,681 total
includes taxes & fees
Sep 21 - Sep 22
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 ￥55,757
￥64,121 total
includes taxes & fees
Sep 21 - Sep 22
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 ￥56,792
￥86,909 total
includes taxes & fees
Sep 30 - Oct 1
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 ￥44,348
￥72,990 total
includes taxes & fees
Oct 2 - Oct 3
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 ￥49,276
￥80,071 total
includes taxes & fees
Oct 2 - Oct 3
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 ￥63,536
￥94,455 total
includes taxes & fees
Oct 2 - Oct 3
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 ￥50,688
￥80,082 total
includes taxes & fees
Oct 2 - Oct 3
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 ￥63,536
￥94,456 total
includes taxes & fees
Oct 11 - Oct 12
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 12 hours ago
Hotel Nyack, a JdV by Hyatt Hotel
Westchester Marriott

Westchester Marriott

8/10 Good
"Stayed here several times, good location, courtyard was pleasant for an evening rest, staff was helpful. Controlling the room temp was an issue and the fan wouldn't turn off. Staff had an engineer solve the problem when we were out for the day. If this weren't an issue, I'd give it a 5 star review."
Thomas 3-night trip
Posted 12 hours ago
Westchester Marriott

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 vacation rental in Chappaqua?

Yes, we offer vacation rentals in Chappaqua near Chappaqua Performing Arts Center, or you can select a more secluded option if you want a relaxing stay. Our travelers 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 vacation home rentals in Chappaqua?

Modern Luxury Home w GameRoom & Parking: You might like this vacation home rental near Chappaqua. It 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 you can cook with friends or family.

How many vacation rentals will I find in Chappaqua?

Expedia has 3 vacation 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 larger area.

What’s a vacation rental in Chappaqua like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Chappaqua. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a family getaway.