Chappaqua Vacation Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Vacation Rentals in Chappaqua

Our top choices for Chappaqua vacation rentals

Stamford Suites

4.0 star property
5.8 out of 10, (52)
"Excellent sleep"
The price is ¥17,918
¥20,606 total
includes taxes & fees
Sep 4 - Sep 5
Stamford Suites

3BR Prime Luxury near NYC w Arcade Room

2.0 star property
8.0 out of 10, Very Good, (1)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
The price is ¥88,928
¥114,186 total
includes taxes & fees
Sep 8 - Sep 9
3BR Prime Luxury near NYC w Arcade Room

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

9.0 out of 10, Wonderful, (7)
"Perfect place to rest. Excellent service! "
The price is ¥22,046
¥43,317 total
includes taxes & fees
Sep 7 - Sep 8
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very Good, (39)
"it was amazing will stay again food was good comfort was great "
The price is ¥38,106
¥43,822 total
includes taxes & fees
Sep 7 - Sep 8
Guesthouse at Norwalk Inn

Global Luxury Suites White Plains

3.5 star property
6.8 out of 10, (32)
"Being in an apartment building for an actual stay instead of a house was a first for myself and the family but overall a good stay."
Global Luxury Suites White Plains

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (122)
"It has an incredible mountain and water view. "
The price is ¥27,910
¥45,682 total
includes taxes & fees
Sep 4 - Sep 5
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

8.8 out of 10, Excellent, (37)
"Short trip. great place to stay . Very cozy . Family loved it "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Modern Luxury Home w GameRoom & Parking

3.0 star property
7.0 out of 10, Good, (4)
"Put down a deposit with the understanding that the deposit would be back in my account within 24 hours. Messaged them several times and I have not gotten any response nor have I gotten my money back and it has been days now with no response. Apartment was filthy, beds were used and not cleaned, bunch of appliances didn’t work, found a towel with stains potentially from bodily fluids.DO NOT BOOK WITH THEM THEY ARE SCAMMERS. Charged a cleaning fee on top of this for an apartment that wasn’t even...
The price is ¥57,157
¥78,642 total
includes taxes & fees
Sep 4 - Sep 5
Modern Luxury Home w GameRoom & Parking

Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

9.0 out of 10, Wonderful, (2)
"I chose this apartment for its location primarily and it was a hit. Since we were traveling and staying for two weeks with a toddler and a new baby I was looking for it to also have an outdoor space, and it was wonderful as seen in the pictures. For personal reasons I had to change my dates a few days before my booking was coming up, the hosts had no problem to accommodate my needs. During our stay, we even had the opportunity to meet the neighbor next door and visit her garden. The neighborhood...
The price is ¥25,238
¥47,884 total
includes taxes & fees
Sep 21 - Sep 22
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

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

8.0 out of 10, Very Good, (16)
"Great place great location"
The price is ¥14,029
¥20,018 total
includes taxes & fees
Sep 8 - Sep 9
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Luxury Living in the Heart of NY

4.0 star property
2.0 out of 10, (1)
"The photos of the unit were beautiful however the wear and tear on the actual property did not compare. The bathroom sink constantly leaked and because the floors were not even they stayed wet. The nightstands were broken the refrigerator would not open all the way. I also was not notified until the day of check in that the unit was on the 3rd floor and there was 2 flights of stairs just to get to the entrance to the unit."
Luxury Living in the Heart of NY

Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

9.0 out of 10, Wonderful, (6)
"Large comfortable home in great location with multiple views of the Hudson. Our family had a pleasant stay and would definitely return to Castle in the Sky."
Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

Elegant Hideaway • Free Parking

Elegant Hideaway • Free Parking

Luxury 5BR 2BA Spacious Home NYC Free Parking + Office

2.0 out of 10, (1)
"If I could give this place zero stars, I would. Upon arrival, I received no check-in information, which immediately set the tone for a frustrating experience. When I got to the property, the front door was already open, raising serious concerns about security. Inside, the floors were dirty, the beds were unmade, and the trash from the previous guests had not been removed. There were bugs throughout the space, and the front door handle was broken, making the property feel unsafe and poorly...
Luxury 5BR 2BA Spacious Home NYC Free Parking + Office

Piermont Oasis

10.0 out of 10, Exceptional, (2)
"Carolyn was so amazing with her directions on how to park and check in. The apartment had everything as advertised. The ambiance was very private and peaceful. Walking distance to the town and pier. I would definitely stay again."
The price is ¥19,448
¥32,738 total
includes taxes & fees
Sep 15 - Sep 16
Piermont Oasis

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

9.8 out of 10, Exceptional, (7)
"Patrick and Katherine are excellent hosts with an incredible property in an amazing location. We had such an incredible time. The carriage house is so comfortable and welcoming. I absolutely loved just sitting on the balcony enjoying the beautiful view, birds, and my coffee. This was my first time using Vrbo, (glad to have found an alternative to another site I no longer support). Wow, I have been missing out!! The stocked fridge was such a lovely surprise. Everything was just fantastic. Our...
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train

9.4 out of 10, Exceptional, (3)
"We only stayed a couple days, but the location is quaint and apartment newly refurnished. The owner was very helpful and great to work with. Highly recommend!"
Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (17)
"cleanliness. quiet. "
Luxury Apartments by Hyatus at The Asher

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (88)
"It was very nice "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

The Subterranean Haven

9.0 out of 10, Wonderful, (8)
"Great space but anlittle amall, the floor dips a few spots and the space is pretty tight, but perfect for a short term stay!"
The price is ¥26,723
¥43,321 total
includes taxes & fees
Sep 7 - Sep 8
The Subterranean Haven
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chappaqua Hotel Reviews

Find out more about Chappaqua

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 near the most popular sights in Chappaqua, or you can select a secluded option if you're looking for relaxation. 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?

3BR Prime Luxury near NYC w Arcade Room: You might like this vacation home rental near Chappaqua. It is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

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. Travelers Rest and Thomas J. Watson Research Center 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.