Chappaqua Holiday Rentals

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Holiday Rentals in Chappaqua

Stamford Suites

4.0 star property
5.8 out of 10, (52)
"Excellent sleep"
The price is AU$228
includes taxes & fees
16 Sept - 17 Sept
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 AU$1,157
includes taxes & fees
16 Sept - 17 Sept
3BR Prime Luxury near NYC w Arcade Room

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

9.4 out of 10, Exceptional, (11)
"Perfect place to rest. Excellent service! "
The price is AU$415
includes taxes & fees
29 Sept - 30 Sept
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 AU$434
includes taxes & fees
22 Sept - 23 Sept
Guesthouse at Norwalk Inn

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 AU$468
includes taxes & fees
16 Sept - 17 Sept
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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

Modern Luxury Home w GameRoom & Parking

3.0 star property
7.2 out of 10, Good, (5)
"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...
Modern Luxury Home w GameRoom & Parking

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

8.8 out of 10, Excellent, (37)
"Very clean, comfortable, and quiet property. Although advertised one car parking, actually can park 2, which is good since limited street parking in a crowded neighborhood. Highly recommended if you're staying in the NYC area."
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

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

9.0 out of 10, Wonderful, (2)
"The owner was very responsive and kind. The apartment was very clean and well updated. We are older adults and the access to the basement apartment was a bit of a challenge but the owner did graciously help with our luggage. The family does clearly disclose that they live above the unit and sounds of children may be heard. Between the sounds of the family above and the fact it’s a basement, not a “Loft”, with all the plumbing just above your head - it was not for us. "
The price is AU$490
includes taxes & fees
21 Sept - 22 Sept
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

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

9.8 out of 10, Exceptional, (7)
"We loved our stay at the Carriage House. Patrick and Kathryn were wonderful hosts. They provided information in a timely manner, and were quick to respond to any questions. Our accommodations were clean, comfortable and well appointed, and Patrick and Kathryn included truly thoughtful touches. The location was perfect for exploring Croton-on-Hudson and the Hudson Valley. We'd love to come back!"
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

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.

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

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 AU$206
includes taxes & fees
21 Sept - 22 Sept
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge

Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge

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 AU$337
includes taxes & fees
29 Sept - 30 Sept
Piermont Oasis

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

10.0 out of 10, Exceptional, (90)
"It was very nice "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

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
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.
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Top Chappaqua Hotel Reviews

Find out more about Chappaqua

Find out more about Chappaqua

Everything you need to know about Chappaqua holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chappaqua holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chappaqua holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chappaqua holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chappaqua. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chappaqua holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chappaqua holiday rentals we have selected for you start as low as AU$206 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chappaqua rentals

At Expedia, we put the best Chappaqua holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chappaqua rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chappaqua holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chappaqua. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Chappaqua?

Yes, there are holiday rentals close to the most popular sights in Chappaqua, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Chappaqua has to offer?

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

How many holiday rentals will I find in Chappaqua?

Expedia has 3 holiday 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 wider area.

What’s a holiday rental in Chappaqua like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chappaqua. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a small group gathering.