Best Vacation Homes in Chappaqua
4100 ft²
4 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $407/Night
For 7 Nights US $2,852
4154.87 ft²
12 Guests
1 Bedroom
6 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $1,361/Night
For 7 Nights US $9,527
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
US $711/Night
For 7 Nights US $4,976
4100 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $372/Night
For 7 Nights US $2,601
974.13 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
US $283/Night
For 7 Nights US $1,983
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $390/Night
For 7 Nights US $2,729
1200 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $426/Night
For 7 Nights US $2,985
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $198/Night
For 7 Nights US $1,383
Chappaqua Luxury Rentals
2 Guests
2 Bedrooms
1 Bathroom
Couples Retreat
Cottage
- Fireplace/Heating
- Air Conditioner
- Laundry
US $3,564/Night
For 7 Nights US $24,948
16 Guests
8 Bedrooms
8 Bathrooms
Ocean View
House
- Private Pool
- Spa
- Fireplace/Heating
US $3,001/Night
For 7 Nights US $21,007
8600 ft²
12 Guests
5 Bedrooms
5 Bathrooms
Group Friendly
House
- Hot Tub
- Child Friendly
- Security/Safety
US $1,708/Night
For 7 Nights US $11,957
4151 ft²
12 Guests
4 Bedrooms
6 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,307/Night
For 7 Nights US $9,148
10 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $1,152/Night
For 7 Nights US $8,066
16 Guests
4 Bedrooms
4 Bathrooms
Group Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $1,115/Night
For 7 Nights US $7,804
16 Guests
4 Bedrooms
4 Bathrooms
Group Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $1,115/Night
For 7 Nights US $7,804
16 Guests
4 Bedrooms
4 Bathrooms
Group Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $1,115/Night
For 7 Nights US $7,804
Chappaqua Pet Friendly Vacation Rentals
800 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $313/Night
For 7 Nights US $2,189
2798.62 ft²
11 Guests
5 Bedrooms
4 Bathrooms
Free Cancellation
House
- Spa
- Fireplace/Heating
- View
US $556/Night
For 7 Nights US $3,894
1 Bedroom
1 Bathroom
Family Friendly
House
- Pool
- Balcony/Terrace
- Pet Friendly
US $1,039/Night
For 7 Nights US $7,271
4 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $224/Night
For 7 Nights US $1,570
4101.05 ft²
4 Guests
3 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
US $634/Night
For 7 Nights US $4,435
2250 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $528/Night
For 7 Nights US $3,695
4284 ft²
13 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $816/Night
For 7 Nights US $5,712
5 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $476/Night
For 7 Nights US $3,333
Chappaqua Large Vacation Homes
2800 ft²
11 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $716/Night
For 7 Nights US $5,010
4000 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
Other
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $850/Night
For 7 Nights US $5,948
2700 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $517/Night
For 7 Nights US $3,619
4144 ft²
12 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,204/Night
For 7 Nights US $8,430
4202 ft²
18 Guests
7 Bedrooms
6 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,863/Night
For 7 Nights US $13,041
11 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Spa
- Fireplace/Heating
- Balcony/Terrace
US $695/Night
For 7 Nights US $4,865
4300 ft²
13 Guests
7 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
US $1,295/Night
For 7 Nights US $9,065
1367 ft²
13 Guests
7 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
US $630/Night
For 7 Nights US $4,410
Why Choose Rent By Owner for your Chappaqua Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Chappaqua
When should you plan your Vacation Rentals stay?
Determining the ideal time to visit this destination can help you enjoy its scenic beauty and local atmosphere at its best, making your stay in the region truly memorable.
Peak Season Highlights
Spring (March to May)
Experience the vibrant awakening of the area during spring, when the landscape blooms with colorful flora. This is a popular time for outdoor activities and enjoying mild temperatures.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 45°F to 55°F
Fall (September to November)
Visit in the fall to enjoy the stunning foliage that transforms the region into a tapestry of reds and oranges. The comfortable weather makes it ideal for exploring scenic outdoor spaces.
Average Temperature Daytime: 55°F to 65°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Summer (June to August)
During summer, the area offers warm weather perfect for outdoor adventures. It’s a quieter time to find more private, peaceful vacation rentals while enjoying longer daylight hours.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 65°F
Winter (December to February)
The winter months bring a serene atmosphere with colder temperatures, ideal for cozy stays in charming vacation rentals and enjoying the tranquility of this destination.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
Weekly Weather Forecast for Chappaqua
How to Book Your Chappaqua Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Chappaqua
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a spacious outdoor seating area, perfect for relaxing or entertaining alfresco in the fresh air.
- Take advantage of a private backyard with lush landscaping, ideal for outdoor activities and gatherings.
- Make the most of a well-maintained patio area, offering a great spot for outdoor dining and barbecues.
- Explore the region’s scenic walking and biking trails directly accessible from the property grounds.
- Relax by a private or community pool, especially during warm weather months.
- Utilize outdoor fire pits or fireplaces for cozy evenings under the stars.
- Benefit from well-kept lawns and gardens that create an inviting outdoor environment for children and pets alike.
Top Attractions Around Chappaqua
What attractions are nearby?
Nearby in this charming area, you can enjoy a variety of outdoor activities and local attractions that highlight the natural beauty and cultural charm of Chappaqua, New York.
Family Activities
- Teatown Lake Reservation: Explore scenic trails and enjoy wildlife watching at this popular nature preserve in the area, perfect for family outdoor adventures.
- Historic Chappaqua Railroad Station: Visit this charming historic site to learn about the area's transportation history and take memorable family photographs.
- Horace Greeley House Museum: Discover the rich local history by touring this well-preserved historic house, appealing to curious minds of all ages.
- Dogwood Park: Spend quality time with your family in this welcoming park, featuring playgrounds and open spaces for picnics and relaxation.
Adult Activities
- Explore the Saw Mill River Audubon Sanctuary: Immerse yourself in nature by walking through this scenic sanctuary, perfect for birdwatching and enjoying peaceful outdoor moments close to your vacation rental.
- Visit local farms and farmers' markets: Experience fresh regional produce and artisanal goods at nearby farms and markets, adding a touch of farm-to-table charm to your stay here.
- Enjoy a round of golf at the local courses: Spend your day playing on well-maintained golf courses that offer a relaxing and engaging activity accessible from your accommodation.
- Discover arts and cultural events at nearby venues: Engage with the vibrant local arts scene through gallery visits, performances, or community events that celebrate the area's creative spirit.
Other Places to Stay in Chappaqua, NY
Westchester County
Town of New Castle
Chappaqua Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Cuisine: Take advantage of the area's charming restaurants and cafes to experience authentic flavors unique to this destination.
- Plan Outdoor Activities: Make the most of your stay by engaging in nearby parks, trails, or natural spots that highlight the region’s scenic beauty.
- Discover Cultural Events: Check local event calendars to immerse yourself in seasonal festivals, markets, or performances that showcase the community's vibrant spirit.
- Choose a Strategic Location: Select accommodations close to key attractions or transport links to maximize your convenience and exploration time in the area.
Transportation Options
- Metro-North Railroad: This regional rail service provides convenient access to New York City and surrounding areas, making it easy to explore the city from your vacation rental in the region.
- Local Bus Services: Multiple local bus routes connect the area to nearby towns and transit hubs, offering a budget-friendly transportation option for your stay.
- Private Car Services and Taxis: Reliable private car and taxi services operate here, providing flexible and direct transportation to and from your vacation rental or local destinations.
- Rental Cars: Many visitors opt to rent vehicles, giving you the freedom to explore the region at your own pace during your vacation in this destination.
Local Customs Options
- Community Events and Parades: You’ll find that participating in local parades and community events is a cherished tradition, reflecting the area's close-knit spirit.
- Farmers' Markets: Visiting the regional farmers’ markets provides insight into the area’s emphasis on fresh, locally sourced produce and handmade goods.
- Historical Respect: Respect for historical sites and local heritage is deeply ingrained, making it common to observe traditions honoring the region’s past.
- Celebration of Seasonal Holidays: Seasonal festivities are celebrated with unique local customs, offering you a glimpse into the area's cultural identity throughout the year.
Chappaqua Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Chappaqua?
There are a lot of options in Chappaqua. If you plan on staying in the Chappaqua area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chappaqua:
- Luxury 8 BR Estate with Pool and Tennis court
- Beautiful Brand New Private Duplex Unit in Lower Hudson Valley "Stone Haven"
- Family home in one of NY top-ranked school districts with Tennis court
- 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
- Neighbor's house - Welcome!
- The Best of Both Worlds: For nature lovers but close to New York City.
- Modern charming country cottage for long term availability
- Clean, Comfy & Convenient 1 Bed Apt in the Village
- Hudson River Views Briarcliff Manor Home with Deck
- Designer Home in Lower Hudson Valley
2. How many vacation rentals have private pools in Chappaqua?
There are 4 vacation rentals with private pools near Chappaqua. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Chappaqua are best for families?
If you are looking for a family-friendly vacation home in Chappaqua, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chappaqua:
4. How many Rentbyowner vacation rentals are available in Chappaqua?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 92 in the Chappaqua area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chappaqua.
5. What is the cancellation policy for vacation rentals in Chappaqua, New York?
Cancellation policies vary depending on the property listing. You should review the specific terms provided in the rental listing or contact the property owner directly to understand the applicable cancellation rules and any associated fees.
6. Are pets allowed in vacation rentals in this destination?
Pet policies differ among properties, so it is essential to check the individual listing details or reach out to the owner to confirm whether pets are permitted during your stay.
7. How do I find available dates for my stay in Chappaqua, New York?
Availability depends on the specific property you are interested in. Use the booking platform’s calendar feature or contact the owner directly to verify current availability for your preferred travel dates.
8. What amenities are typically included in vacation rentals here?
Amenities can vary but often include essentials like Wi-Fi, kitchen facilities, and parking. To ensure the property meets your needs, review the detailed listing description or inquire with the host about specific amenities.
9. Who do I contact if I have questions before booking my vacation rental?
You can reach out to the property owner or manager through the messaging system provided on the booking platform. They can answer any specific questions about the property, policies, or the area to help you prepare for your stay.
Chappaqua Top Rated Vacation Rentals
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
US $169/Night
For 7 Nights US $1,185
US $164/Night
For 7 Nights US $1,150
322.92 ft²
22 Guests
117 Bedrooms
1 Bathroom
Ocean View
Hotel
- Oceanfront
- Fireplace/Heating
- Pool
US $313/Night
For 7 Nights US $2,188
16 Guests
4 Bedrooms
4 Bathrooms
Group Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $1,115/Night
For 7 Nights US $7,804
12 Guests
3 Bedrooms
3 Bathrooms
Group Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $836/Night
For 7 Nights US $5,855
12 Guests
3 Bedrooms
3 Bathrooms
Group Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $836/Night
For 7 Nights US $5,855
12 Guests
3 Bedrooms
3 Bathrooms
Group Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $836/Night
For 7 Nights US $5,855
12 Guests
3 Bedrooms
3 Bathrooms
Group Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $836/Night
For 7 Nights US $5,855
