Chappaqua Holiday Rentals

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Our top choices for Chappaqua holiday rentals

Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC
4.0 star property
Southeast Yonkers
2.0 out of 10, (3 reviews)
"We never got to stay because THERE WAS ANOTHER FAMILY THERE. THAT WOMEN SAID SHE WAS RENTING THE HOUSE FOR ANOTHER MONTH. "
United States
Angel
The price is AU$926
includes taxes & fees
9 June - 10 June
Modern Comfort in the Heart of NYC

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
The price is AU$3,295
includes taxes & fees
12 June - 13 June
Luxury NYC Home Game Room Free Parking

Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
5.6 out of 10, (8 reviews)
"Property bedding was dirty, carpet dirty, sofas were dirty. Not was listed in the pictures. Asked me for $900 deposit through Zelle. No respond. Expedia needs to investigate this company for false advertising. "
United States
Liliana
The price is AU$2,139
includes taxes & fees
9 June - 10 June
Modern Luxury Home w GameRoom & Parking

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is AU$1,713
includes taxes & fees
9 June - 10 June
Prime Luxe 3-BR NYC - Free Parking

Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is AU$3,227
includes taxes & fees
9 June - 10 June
Two Wash

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 AU$624
includes taxes & fees
9 June - 10 June
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

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 AU$2,907
includes taxes & fees
9 June - 10 June
Luxury 3 BR Near NYC with Easy Parking

Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is AU$2,368
includes taxes & fees
23 June - 24 June
Summer Pool Oasis Custom Bar Arcade Pool Table

Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
8.0 out of 10, Very good, (1 review)
"The house was very clean and the areas was quiet too. We had a nice spot to park the car. The staff was calling and checking on me if I didn’t have any issues with the check in. They were available all the time. The only thing we will need next time if possible is the washer and dryer and extra towels because we were 5 and only got 3 towels. But overall we enjoyed the stays."
United States
Adj Fatou
The price is AU$1,813
includes taxes & fees
9 June - 10 June
Uscale 2BR Escape in the Heart of NYC

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
2.0 out of 10, (1 review)
"Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere."
United States
Kathleen
The price is AU$965
includes taxes & fees
12 June - 13 June
Luxury NYC Home with Free Parking for 12

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
2.0 out of 10, (1 review)
"Very inaccurate listing upon arriving host called me stating I could not stay at property due to issues on their end instead of offering a refund I was sent to a different property that was a 1 bedroom with 1 bed that was clearly not cleaned instead of the 3 bedroom 5 bed luxury house I initially booked I explained this would not work for me and my 4 other guests and got told there was no other choice and hung up on, me and my guests had no option beside to go back home very bad experience DO...
United States
Gerald
The price is AU$3,227
includes taxes & fees
9 June - 10 June
Spacious 3BR Luxe Escape near NYC

NY Luxury Apt Free Parking in PRIME Area

NY Luxury Apt Free Parking in PRIME Area
3.0 star property
Southeast Yonkers
4.4 out of 10, (5 reviews)
"Everything about this place is amazing. Great location, very safe, cozy, clean. Will be back soon!"
United States
Paola
The price is AU$926
includes taxes & fees
15 June - 16 June
NY Luxury Apt Free Parking in PRIME Area

Luxury 5 BR Home Free Parking

Luxury 5 BR Home Free Parking
2.0 star property
Bryn Mawr
2.0 out of 10, (1 review)
The price is AU$3,704
includes taxes & fees
9 June - 10 June
Luxury 5 BR Home Free Parking

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is AU$574
includes taxes & fees
9 June - 10 June
Guesthouse at Norwalk Inn

3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
The price is AU$1,792
includes taxes & fees
9 June - 10 June
3BR Prime Luxury NY - Free Parking

Ossining Vacation Rental Near River, Trails & Mta!

Ossining Vacation Rental Near River, Trails & Mta!
3.0 star property
Ossining
The price is AU$1,252
includes taxes & fees
14 June - 15 June
Ossining Vacation Rental Near River, Trails & Mta!

Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
6.8 out of 10, (3 reviews)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is AU$3,227
includes taxes & fees
9 June - 10 June
Luxury 3BR Family Home Game Room Parking

Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
4.8 out of 10, (6 reviews)
"Everything was clean, good communication.. I would like to come back again for sure "
United States
Genesis
The price is AU$767
includes taxes & fees
9 June - 10 June
Luxury 1BR located in Prime Yonkers Area

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
8.0 out of 10, Very good, (2 reviews)
"Room was cold. No parking lot for vehicle. Only off-street parking was available "
United States
david
The price is AU$926
includes taxes & fees
9 June - 10 June
Spacious 3BR Luxe Escape near NYC

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (125 reviews)
"Was a good Hotel friendly and clean"
United States
Tamara
The price is AU$243
includes taxes & fees
22 June - 23 June
Stamford Suites
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

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$194 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. 

Explore a world of travel with Expedia

Frequently asked questions

Can I find a holiday rental in Chappaqua?

Yes, there are holiday rentals in Chappaqua close to Chappaqua Performing Arts Center, 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?

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: This holiday home rental outside of Chappaqua is located next to a golf course, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as table football.

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. Chappaqua Performing Arts Center and Jacob Burns Film Center Theater 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.