Chappaqua holiday lettings

We found 212 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Chappaqua to find one that's perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a fireplace. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.

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The lively area of Chappaqua awaits your stay

The area's opera and entertainment are just some of the reasons to come on holiday to Chappaqua. This city is well-known for its sporting events and restaurants. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Chappaqua

Are you hoping to discover things to do while you're in the area? Venture out of your holiday home and check out everything that makes Chappaqua a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Rockland Lake State Park Championship Golf Course (8 mi / 12.9 km)
  • Rockland Bakery (12.9 mi / 20.7 km)
  • Hand & Stone Massage and Facial Spa (13 mi / 20.9 km)
  • Rye Playland (14.2 mi / 22.8 km)
  • Legoland Discovery Center Westchester (14.2 mi / 22.9 km)
  • Chelsea Piers (15 mi / 24.1 km)

Exploring the natural landscape of Chappaqua

Whether you're an outdoor enthusiast or just want to take in the scenery, Chappaqua is a great place to spend some time outside. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Rockefeller State Park Preserve (5.1 mi / 8.2 km)
  • Croton Point Park (6.9 mi / 11.1 km)
  • Silver Lake Park (7.9 mi / 12.7 km)
  • Nyack Beach State Park (8.1 mi / 13.1 km)
  • Rockland Lake State Park (8.6 mi / 13.8 km)
  • Houston Preserve (10 mi / 16.1 km)

How to get to and around Chappaqua

Fly into White Plains, NY (HPN-Westchester County), the closest airport, located 7 mi (11.3 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Danbury, CT (DXR-Danbury Municipal), which is 20.6 mi (33.2 km) away.

Frequently asked questions

What is the best area to stay in Chappaqua when booking a holiday rental?
When considering a holiday rental in Chappaqua, New York, the area around the town centre is an excellent choice. This charming neighbourhood offers a picturesque setting with a blend of modern amenities and quaint, small-town charm. Visitors can enjoy the beautiful landscapes and well-maintained parks that characterise the area, making it great for leisurely strolls.

One of the top attractions nearby is the Chappaqua Crossing, which features an array of shops and dining options, allowing for a delightful day out. Additionally, the Horace Greeley House, once the home of the great newspaper editor, is a point of interest that offers a glimpse into local history.

Chappaqua has a variety of properties available, suiting different preferences, whether you're looking for a cosy cottage or a spacious family home.
How much does it cost to rent a holiday home in Chappaqua?
Prices for holiday rentals in Chappaqua vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chappaqua to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chappaqua holiday house rentals?
You can find great discounts on house rentals in Chappaqua on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Chappaqua?
In Chappaqua, holiday houses are the predominant type of holiday rental, with several available throughout the area. These spacious properties typically include multiple bedrooms, fully equipped kitchens for convenient meal preparation, and comfortable living areas ideal for relaxation. Many of these homes also feature outdoor spaces such as gardens or patios, superb for enjoying the serene surroundings.
Are there any family house rentals in Chappaqua?
In Chappaqua, New York, there are several family-friendly house rentals available, making it an excellent choice for visitors seeking a comfortable stay. The neighbourhood offers a selection of spacious homes with inviting living areas and outdoor spaces for children to play. Many properties come equipped with full kitchens, allowing families to prepare meals together, while amenities such as Wi-Fi and air conditioning ensure a pleasant experience.

Nearby, families can explore local parks, which often feature playgrounds and picnic areas, providing opportunities for outdoor fun. The charming downtown area boasts shops and restaurants, offering a taste of the community's vibrant setting.
Can I find long-stay holiday rentals in Chappaqua?
A long-stay holiday rental in Chappaqua is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Chappaqua?
In Chappaqua, there are several pet-friendly house rentals available, offering a welcoming environment for travellers with furry companions. The area is known for its charming suburban feel, with properties typically featuring spacious layouts, fenced yards, and amenities such as modern kitchens and comfortable living areas. Many rentals also provide outdoor spaces, ideal for pets to play and relax.

Chappaqua is surrounded by beautiful parks and nature reserves, great for leisurely walks with your pet. Notable nearby spots include the scenic Chappaqua Crossing, which has walking trails and open spaces, as well as the larger parks in the region that offer additional opportunities for outdoor adventures.
Are there any remote work holiday rentals in Chappaqua?
In Chappaqua, New York, there are several holiday rentals that cater to remote work needs. Many of these properties are equipped with amenities such as free Wi-Fi, dedicated workspaces, and comfortable desk chairs, making them ideal for professionals looking to work from home while enjoying a change of scenery.

The area itself is known for its picturesque surroundings and tranquil atmosphere, great for a productive work environment. Chappaqua's charming downtown offers local cafes and shops, providing convenient options for breaks or casual meetings. Additionally, the nearby nature trails and parks offer great opportunities for relaxation after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chappaqua holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chappaqua with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chappaqua?
In Chappaqua, popular rental amenities cater to a comfortable and enjoyable stay. Many holiday rentals feature outdoor spaces such as decks or patios, ideal for relaxing in the fresh air. Fireplaces are common, providing a warm and inviting atmosphere, especially during the cooler months. Additionally, you can expect to find porches or lanais, offering further opportunities to enjoy the surroundings. Most accommodations also include a fully equipped kitchen, allowing guests to prepare their own meals, and amenities like blenders for convenient meal preparation or smoothies.
When is the best time to visit Chappaqua for a holiday rental?
April is a wonderful time to visit Chappaqua, as it marks the beginning of spring and brings vibrant blooms throughout the area. During this month, the pleasant temperatures (around 10 to 15 degrees Celsius) make it ideal for outdoor activities, such as leisurely walks in the charming downtown or exploring the nearby nature trails.

The peak season in Chappaqua typically runs from August to October, when visitors flock to enjoy the beautiful autumn foliage and partake in local festivals. The crisp air and stunning fall colours create a picturesque backdrop for sightseeing and outdoor activities, attracting those who appreciate the beauty of nature.

For travellers looking for a more budget-friendly option, December can be a delightful time to visit. While it's considered low season, the holiday decorations and festive spirit create a warm and inviting atmosphere. Visitors can enjoy the quiet charm of Chappaqua while exploring local shops and cafes.
How early should I book a Chappaqua holiday rental?
Book your Chappaqua holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chappaqua?
In Chappaqua, visitors can enjoy a quaint suburban charm alongside various attractions. The town is known for its beautiful parks, such as the scenic Gedney Park, which features walking paths, picnic areas, and sports facilities, making it a great spot for outdoor activities.

The Chappaqua Performing Arts Centre is a cultural hub, offering a range of performances throughout the year, from theatre productions to concerts, providing entertainment for all ages.

For those interested in local history, the Horace Greeley House, the former home of the famous journalist and editor, is an intriguing site that reflects the town's rich heritage.
Can I change or cancel my Chappaqua home rental booking on Vrbo?
To find Chappaqua holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Chappaqua holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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