Chappaqua Holiday Rentals

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Holiday Rentals in Chappaqua

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
9.6 out of 10, Exceptional, (18)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
The price is AU$289
includes taxes & fees
26 Oct - 27 Oct
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 "
United States
anthony
The price is AU$455
includes taxes & fees
9 Nov - 10 Nov
Guesthouse at Norwalk Inn
Cozy 1-bedroom retreat minutes from West Point!
10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is AU$290
includes taxes & fees
23 Oct - 24 Oct
Cozy 1-bedroom retreat minutes from West Point!
Private room, 5 min walk to restaurant, 40 min to NYC. 5 min drive to MetroNorth
2.0 star property
The price is AU$179
includes taxes & fees
23 Oct - 24 Oct
Private room, 5 min walk to restaurant, 40 min to NYC. 5 min drive to MetroNorth
Piermont Oasis
10.0 out of 10, Exceptional, (5)
"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."
United States
Anonymous traveller
The price is AU$325
includes taxes & fees
28 Oct - 29 Oct
Piermont Oasis
Modern Luxe 1BR Apt in Downtown Stamford
9.6 out of 10, Exceptional, (5)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is AU$571
includes taxes & fees
23 Oct - 24 Oct
Modern Luxe 1BR Apt in Downtown Stamford
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
The price is AU$392
includes taxes & fees
2 Nov - 3 Nov
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
10.0 out of 10, Exceptional, (5)
"We had an excellent stay! Our hosts were kind and helpful. The home was modern and very well kept, very clean. I would highly recommend this location and home to anyone traveling in the area."
United States
Suzanne A.
The price is AU$493
includes taxes & fees
30 Oct - 31 Oct
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
The Mansion Hotel-style
4.5 star property
The price is AU$250
includes taxes & fees
23 Oct - 24 Oct
The Mansion Hotel-style
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
8.0 out of 10, Very good, (17)
"Great place great location"
United States
Daquan H.
The price is AU$210
includes taxes & fees
30 Oct - 31 Oct
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Seabreeze at the beach west beach Stamford ct.
9.8 out of 10, Exceptional, (6)
"Very nice! Easy to work with and house was what we expected. "
United States
Jack P.
The price is AU$630
includes taxes & fees
10 Nov - 11 Nov
Seabreeze at the beach west beach Stamford ct.
House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (2)
"Good stay, awesome place"
United States
Scott G.
The price is AU$595
includes taxes & fees
23 Oct - 24 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!
Charming 1-bedroom apartment in Carmel with WiFi, AC
9.0 out of 10, Wonderful, (2)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is AU$373
includes taxes & fees
1 Nov - 2 Nov
Charming 1-bedroom apartment in Carmel with WiFi, AC
45 Minutes from NYC, Entire House near Stamford Downtown,
10.0 out of 10, Exceptional, (19)
"Very nice property. Owner was very nice and quickly answered any questions we had. Well stocked pantry and fridge!! We enjoyed our stay and property was very convenient and comfortable. "
United States
Lisa B.
The price is AU$745
includes taxes & fees
4 Nov - 5 Nov
45 Minutes from NYC, Entire House near Stamford Downtown,
Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (1)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
The price is AU$741
includes taxes & fees
29 Oct - 30 Oct
Sleek Escape: Modern 3 BR- 4 Min from West Point !
New Modern Apartment
10.0 out of 10, Exceptional, (4)
"great place to stay at absolutely comfortable and great neighborhood!"
United States
fransheska r.
The price is AU$365
includes taxes & fees
12 Nov - 13 Nov
New Modern Apartment
Stamford Suites
4.0 star property
5.8 out of 10, (65)
"Location very good."
United States
Sheila
The price is AU$234
includes taxes & fees
26 Oct - 27 Oct
Stamford Suites
The Hideaway
10.0 out of 10, Exceptional, (6)
"Me and my family stayed here for a quick get-away out of the city. Very pretty location, and loved our stay here! Thanks!"
United States
Rick C.
The price is AU$491
includes taxes & fees
23 Oct - 24 Oct
The Hideaway
Penthouse Perfection: with Unmatched Skyline Views
2.0 star property
10.0 out of 10, Exceptional, (9)
"Absolutely amazing place! You can tell it was made with love and we felt right at home from the minute we walked in. Spacious, clean, beautiful! Definitely recommend "
United States
Yuliya S.
The price is AU$742
includes taxes & fees
29 Oct - 30 Oct
Penthouse Perfection: with Unmatched Skyline Views
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
9.2 out of 10, Wonderful, (9)
"loved walking the city. pizza was good."
United States
michelle b.
The price is AU$419
includes taxes & fees
25 Oct - 26 Oct
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to 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$210 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.