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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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 P17,170
P51,255 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, (189 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is P9,499
P10,923 total
includes taxes & fees
Oct 14 - Oct 15
Stamford Suites
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.

3. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is P37,542
P73,221 total
includes taxes & fees
Nov 4 - Nov 5
Summer Pool Oasis Custom Bar Arcade Pool Table
A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

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, (2 reviews)
"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 P25,443
P39,582 total
includes taxes & fees
Oct 14 - Oct 15
Luxury NYC Home with Free Parking for 12
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

West Gate Inn Nyack

West Gate Inn Nyack

8/10 Good
"We had a family event to attend in Nyack so we chose to stay here. The staff was very nice and made us feel welcomed. The rooms had an outdated feel but were functional and clean. The beds were comfortable and the bathrooms were satisfactory. The free breakfast was appreciated. Good selection of hot and cold items. We enjoyed the pancakes, French toast, yogurt, and muffins. Coffee was good, too. For the price, this hotel was a solid choice for a long weekend. Parking was included and convenient as well."
Cheryl 3-night trip
Posted 2 hours ago
West Gate Inn Nyack

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 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.