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
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Chappaqua vacation rentals

Terrace/patio

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
The price is ￥15,079
￥21,516 total
includes taxes & fees
Apr 30 - May 1
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Outdoor dining

Stamford : The Comfy Cove Hideout

Stamford : The Comfy Cove Hideout
Cove - East Side - Shippan
The price is ￥15,079
￥43,511 total
includes taxes & fees
May 29 - May 30
Stamford : The Comfy Cove Hideout
Luxury Apartment | Living area

NY Luxury Apt Free Parking in PRIME Area

NY Luxury Apt Free Parking in PRIME Area
3.0 star property
Southeast Yonkers
5.0 out of 10, (4 reviews)
"Everything about this place is amazing. Great location, very safe, cozy, clean. Will be back soon!"
United States
Paola
The price is ￥17,216
￥35,042 total
includes taxes & fees
May 1 - May 2
NY Luxury Apt Free Parking in PRIME Area
Apartment (1 Bedroom) | Interior

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
The price is ￥17,553
￥53,297 total
includes taxes & fees
May 13 - May 14
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Property grounds

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (16 reviews)
"Cute little place we really enjoyed it and the town"
United States
Ezra S.
The price is ￥19,289
￥33,733 total
includes taxes & fees
May 6 - May 7
Piermont Oasis
Private kitchen

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is ￥21,520
￥44,226 total
includes taxes & fees
May 3 - May 4
Charming 1-bedroom apartment in Carmel with WiFi, AC
Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.6 out of 10, (110 reviews)
"Was very nice & clean. "
United States
Kelly
The price is ￥20,808
￥23,929 total
includes taxes & fees
May 3 - May 4
Stamford Suites
Villa, Garden View | Living area

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
The price is ￥52,658
￥84,002 total
includes taxes & fees
May 1 - May 2
Luxury NYC Home Game Room Free Parking
Luxury Apartment | Living area

Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
The price is ￥42,790
￥71,647 total
includes taxes & fees
May 1 - May 2
Luxury 3 BR Near NYC with Easy Parking
TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is ￥13,571
￥28,555 total
includes taxes & fees
May 6 - May 7
Cozy 1-bedroom retreat minutes from West Point!
Private kitchen

Modern 1BR Apt / Free Parking / Near NYC

Modern 1BR Apt / Free Parking / Near NYC
White Plains
10.0 out of 10, Exceptional, (1 review)
"Very clean, fully stocked with all you need to cook full meals. If coming back to the area, 10/10 would stay again."
United States
Mike J.
The price is ￥14,347
￥48,864 total
includes taxes & fees
Apr 30 - May 1
Modern 1BR Apt / Free Parking / Near NYC
Luxury House | Living area

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
The price is ￥55,634
￥87,384 total
includes taxes & fees
May 6 - May 7
Luxury 3BR Home Game Room Free Parking
Fridge, oven, stovetop, coffee/tea maker

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (20 reviews)
"Very good communication and helpful. "
United States
Liam C.
The price is ￥18,351
￥48,968 total
includes taxes & fees
May 5 - May 6
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Dining

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is ￥47,871
￥77,092 total
includes taxes & fees
May 1 - May 2
Prime Luxe 3-BR NYC - Free Parking
Luxury House | Living area

Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is ￥59,839
￥90,721 total
includes taxes & fees
May 1 - May 2
Two Wash
Fridge, microwave, oven, stovetop

Stylish Home With Free ParkingFA

Stylish Home With Free ParkingFA
Downtown Stamford
The price is ￥26,808
￥40,004 total
includes taxes & fees
May 3 - May 4
Stylish Home With Free ParkingFA
Apartment (4 Bedrooms) | Interior

Easy NYC Access! Yonkers Apt 1/2 Mi to Metro-north

Easy NYC Access! Yonkers Apt 1/2 Mi to Metro-north
3.5 star property
Southeast Yonkers
The price is ￥78,030
￥168,645 total
includes taxes & fees
Apr 30 - May 1
Easy NYC Access! Yonkers Apt 1/2 Mi to Metro-north
Living area

Comfortable 3BR Home / 4 Queen Beds / Free Parking / Perfect for Groups

Comfortable 3BR Home / 4 Queen Beds / Free Parking / Perfect for Groups
White Plains
The price is ￥43,041
￥82,047 total
includes taxes & fees
May 5 - May 6
Comfortable 3BR Home / 4 Queen Beds / Free Parking / Perfect for Groups
Offices

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
The price is ￥22,978
￥50,201 total
includes taxes & fees
Apr 30 - May 1
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
3 bedrooms, desk, iron/ironing board, travel crib

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.2 out of 10, Wonderful, (15 reviews)
"Sweet abode. Cozy, clean and amazing location. The cute coffee bar was a nice bonus. Would definitely stay there again. "
United States
Danica J.
The price is ￥21,063
￥69,800 total
includes taxes & fees
May 3 - May 4
Local Artist Inspired | Walk to WestPoint + King Bed
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

Amsterdam Hotel

Amsterdam Hotel

10/10 Excellent
"For the price ,it was clean ,good stuff size room ,clean bathroom,friendly staff,carpet need little love little old ,but I will stay again ..compare to those expensive hotel"
Khalid 1-night trip
Posted 1 hour ago
Amsterdam Hotel

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: This vacation home rental near Chappaqua is situated near the airport and has a rooftop terrace and 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 Jacob Burns Film Center Theater 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.