Chappaqua Holiday Rentals

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Our top choices for Chappaqua holiday rentals

Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
Bryn Mawr
The price is AU$767
includes taxes & fees
10 Mar - 11 Mar
Luxe 1BR Oasis - Prime NY Stay

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$536
includes taxes & fees
16 Mar - 17 Mar
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$824
includes taxes & fees
10 Mar - 11 Mar
Luxury 3 BR Near NYC with Easy Parking

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
The price is AU$536
includes taxes & fees
10 Mar - 11 Mar
Luxury 3BR Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
The price is AU$1,107
includes taxes & fees
10 Mar - 11 Mar
Luxury NYC Home Game Room Free Parking

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is AU$536
includes taxes & fees
10 Mar - 11 Mar
Elegant Hideaway with Free Parking

NEW 45 Wolden Rd Ossining NY 10562

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
Ossining
The price is AU$1,508
includes taxes & fees
15 Mar - 16 Mar
NEW 45 Wolden Rd Ossining NY 10562

Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is AU$1,724
includes taxes & fees
10 Mar - 11 Mar
Two Wash

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (41 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is AU$587
includes taxes & fees
10 Mar - 11 Mar
Guesthouse at Norwalk Inn

Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
10.0 out of 10, Exceptional, (2 reviews)
"Everything was clean, good communication.. I would like to come back again for sure "
United States
Genesis
The price is AU$783
includes taxes & fees
10 Mar - 11 Mar
Luxury 1BR located in Prime Yonkers Area

3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
The price is AU$1,796
includes taxes & fees
10 Mar - 11 Mar
3BR Prime Luxury NY - Free Parking

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (102 reviews)
"Nice clean rooms the bedding was comfortable, it smelled good walking in, I will be staying in this hotel in the next time I'm in Stamford."
United States
Fatima
The price is AU$243
includes taxes & fees
10 Mar - 11 Mar
Stamford Suites

3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room
2.0 star property
Southeast Yonkers
8.0 out of 10, Very good, (1 review)
"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."
United States
Anonymous traveller
The price is AU$1,137
includes taxes & fees
10 Mar - 11 Mar
3BR Prime Luxury near NYC w Arcade Room

Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
10.0 out of 10, Exceptional, (1 review)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is AU$767
includes taxes & fees
10 Mar - 11 Mar
Luxury 3BR Family Home Game Room Parking

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 AU$314
includes taxes & fees
10 Mar - 11 Mar
NY Luxury Apt Free Parking in PRIME Area

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is AU$1,717
includes taxes & fees
10 Mar - 11 Mar
Prime Luxe 3-BR NYC - Free Parking

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$782
includes taxes & fees
10 Mar - 11 Mar
Uscale 2BR Escape in the Heart of NYC

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$857
includes taxes & fees
10 Mar - 11 Mar
Spacious 3BR Luxe Escape near NYC

Luxury NY Home with Free Parking

Luxury NY Home with Free Parking
4.0 star property
White Plains
8.0 out of 10, Very good, (1 review)
"Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine. "
United States
Safiya
The price is AU$905
includes taxes & fees
10 Mar - 11 Mar
Luxury NY Home with Free Parking

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, (1 review)
The price is AU$900
includes taxes & fees
10 Mar - 11 Mar
Modern Comfort in the Heart of NYC
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$243 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 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?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This holiday home rental outside of Chappaqua is equipped with a garden, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

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 Westchester Skating Academy, 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.