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Chappaqua Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chappaqua vacation rentals

A hallway with hardwood flooring, a staircase, and a dining area with a chair and table.

1. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
3.0 star property
Ossining
The price is NT$8,715
NT$26,017 total
includes taxes & fees
Oct 21 - Oct 22
Snow Days & City Escapes: Spacious Ossining Home
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

2. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (192 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is NT$4,163
NT$4,787 total
includes taxes & fees
Oct 14 - Oct 15
Stamford Suites
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

3. 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 NT$11,461
NT$13,180 total
includes taxes & fees
Oct 14 - Oct 15
Guesthouse at Norwalk Inn
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

4. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is NT$17,226
NT$34,318 total
includes taxes & fees
Nov 3 - Nov 4
Summer Pool Oasis Custom Bar Arcade Pool Table
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

5. 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 NT$15,802
NT$22,831 total
includes taxes & fees
Oct 14 - Oct 15
Luxury NYC Home Game Room Free Parking
A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

6. 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, (3 reviews)
"It was a fraude. You pay but property Is not to rent. I lost my money."
United States
daniel
The price is NT$12,929
NT$20,114 total
includes taxes & fees
Oct 14 - Oct 15
Luxury NYC Home with Free Parking for 12
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

7. 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 NT$5,718
NT$11,296 total
includes taxes & fees
Oct 14 - Oct 15
Elegant Hideaway with Free Parking
A breakfast buffet with pastries, fruits, and a coffee station.

8. 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 NT$28,732
NT$36,756 total
includes taxes & fees
Oct 14 - Oct 15
3BR Prime Luxury NY - Free Parking
A dining table with a glass top, a vase with flowers, and a variety of pastries and fruits.

9. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is NT$27,295
NT$35,157 total
includes taxes & fees
Oct 14 - Oct 15
Prime Luxe 3-BR NYC - Free Parking
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

10. 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 NT$10,027
NT$16,294 total
includes taxes & fees
Oct 14 - Oct 15
Uscale 2BR Escape in the Heart of NYC
A cozy living room with a sofa, a coffee table with a vase of flowers, a bookshelf, and a small kitchen area with a refrigerator and sink.

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 NT$10,503
NT$16,120 total
includes taxes & fees
Oct 18 - Oct 19
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
A flat-screen TV mounted on a black entertainment center in a room with a dining area visible through the glass door.

12. Home & Away Hotel-Style

Home & Away Hotel-Style
2.0 star property
Bronx
The price is NT$8,619
NT$10,003 total
includes taxes & fees
Oct 27 - Oct 28
Home & Away Hotel-Style
A modern living room with a beige sectional sofa, a green armchair, a marble-patterned rug, a gold coffee table, and a flat-screen TV mounted on a white wall.

13. Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
4.0 out of 10, (7 reviews)
The price is NT$9,025
NT$14,853 total
includes taxes & fees
Oct 14 - Oct 15
Luxury 3BR Family Home Game Room Parking
A modern living room with a sofa, armchairs, a coffee table, and a dining area with a table and chairs.

14. Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is NT$27,295
NT$35,293 total
includes taxes & fees
Oct 14 - Oct 15
Two Wash
A modern kitchen with white cabinets, a central island with stools, a stone accent wall, a flat-screen TV, and a beige sofa with teal cushions.

15. 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 NT$10,315
NT$16,296 total
includes taxes & fees
Oct 14 - Oct 15
Luxury 1BR located in Prime Yonkers Area
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

16. Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
2.0 out of 10, (1 review)
"This is a scam and at the same time others guest’s was there for same booking but we can’t get any feed the property support and we returned from the property and kids suffered a lot!!!"
United States
Md Asadul
The price is NT$11,557
NT$17,686 total
includes taxes & fees
Oct 14 - Oct 15
Luxury 3 BR Near NYC with Easy Parking
A modern living room with a stone wall, a flat-screen TV, a white sofa, and a kitchen area with a bar counter and chairs.

17. 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 NT$10,027
NT$15,975 total
includes taxes & fees
Oct 14 - Oct 15
Luxe 1BR Oasis - Prime NY Stay
A modern living room with a sofa, armchairs, and a glass coffee table.

18. 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 NT$18,676
NT$25,650 total
includes taxes & fees
Oct 14 - Oct 15
Luxury 5 BR Home Free Parking
A modern kitchen with white cabinetry, a dining area with a glass table, and a view of the outdoors through large windows.

19. 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 NT$12,929
NT$19,221 total
includes taxes & fees
Oct 14 - Oct 15
Modern Comfort in the Heart of NYC
A modern living room with a white sofa, a glass coffee table, and a marble-patterned rug.

20. 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 NT$38,756
NT$48,115 total
includes taxes & fees
Oct 14 - Oct 15
Modern Luxury Home w GameRoom & Parking
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

Tarrytown House Estate

Tarrytown House Estate

8/10 Good
"Hotel grounds were gorgeous. The rooms however need updating. Wonderful historic charm of the overall place, but 1970’s feel to the individual rooms"
Christopher 2-night trip
Posted less than an hour ago
Tarrytown House Estate

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
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  • 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 Rockefeller State Park Preserve 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.