58+ Vacation Rentals & Holiday Homes in Chappaqua |
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Chappaqua Accommodations - Hotels & Rentals

About Chappaqua Vacation Rentals

Discover More than 58 Incredible Getaway Rentals Available in Chappaqua. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Chappaqua.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Chappaqua, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Chappaqua. The Average Size of Places to Stay Near Chappaqua is 1291.86 ft², with Prices Averaging US $704 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Chappaqua. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Chappaqua

Type Count
Vacation Homes 35
Holiday Apartments 10
Cottages 3
Villas 1

Use these Quick Filters to Find a Vacation Rental in Chappaqua

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Chappaqua with Online Reservations.

Weather in Chappaqua, NY

View the weather forecast for Chappaqua before booking your Chappaqua Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities ChappaquaGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World ChappaquaGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Bear Mountain State Park
United States Military Academy
Capitol Theatre
Empire City Casino
Palisades Center
Westchester County Center
New Roc City
Purchase College
Norwalk Maritime Aquarium
Rye Playland
Ridgefield Playhouse
Van Cortlandt Park
Westchester Broadway Theatre
Tarrytown Music Hall
Pelham Bay Park
Yonkers Raceway
The Westchester Mall
Nyack College
Iona College
Historic South Norwalk

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Westchester County 497 Properties
Town of New Castle 44 Properties

Frequently Asked Questions About Chappaqua?

What are the top hotels, lake houses & vacation rentals in Chappaqua?

We provide an array of great vacation destinations in Chappaqua. If you are looking to stay in or around the Chappaqua area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Chappaqua:

Which hotel, lake house, or vacation rental in Chappaqua is best for families?

Searching for a family-friendly getaway in Chappaqua? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Chappaqua?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 58 in the Chappaqua area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Chappaqua.


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