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Chappaqua Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Chappaqua holiday rentals

Desk, free WiFi, bed sheets

1. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (2 reviews)
"Great stay!"
United States
Ann S.
The price is HK$1,403
HK$2,663 total
includes taxes & fees
16 Aug - 17 Aug
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Private kitchen

2. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is HK$1,405
HK$2,776 total
includes taxes & fees
14 Aug - 15 Aug
Elegant Hideaway with Free Parking
Property grounds

3. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
7.6 out of 10, Good, (4 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is HK$861
HK$1,211 total
includes taxes & fees
11 Aug - 12 Aug
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Dining

4. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Smart TV, video games, DVD player, books

5. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (7 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is HK$2,062
HK$3,704 total
includes taxes & fees
11 Aug - 12 Aug
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Interior

6. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is HK$1,687
HK$2,149 total
includes taxes & fees
16 Aug - 17 Aug
1BR Queen near NYC | Trails, Biking & Sauna Bliss
Property grounds

7. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (20 reviews)
"Great place to stay! "
United States
Megan D.
The price is HK$941
HK$1,643 total
includes taxes & fees
7 Sept - 8 Sept
Piermont Oasis
Interior

8. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is HK$1,114
HK$2,274 total
includes taxes & fees
10 Aug - 11 Aug
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
5 bedrooms

9. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is HK$6,032
HK$10,503 total
includes taxes & fees
1 Sept - 2 Sept
Summer Pool Oasis Custom Bar Arcade Pool Table
Outdoor banquet area

10. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.6 out of 10, Excellent, (8 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is HK$5,335
HK$9,525 total
includes taxes & fees
10 Aug - 11 Aug
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Smart TV

11. Spacious 3BR Home / Free Parking / Perfect for Families & Groups

Spacious 3BR Home / Free Parking / Perfect for Families & Groups
White Plains
The price is HK$4,229
HK$7,062 total
includes taxes & fees
10 Aug - 11 Aug
Spacious 3BR Home / Free Parking / Perfect for Families & Groups
TV

12. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is HK$898
HK$1,690 total
includes taxes & fees
11 Aug - 12 Aug
Cozy 1-bedroom retreat minutes from West Point!
3 bedrooms, iron/ironing board, Internet, bed sheets

13. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
White Plains
The price is HK$3,883
HK$6,523 total
includes taxes & fees
10 Aug - 11 Aug
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
Living area

14. 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 HK$3,883
HK$5,610 total
includes taxes & fees
10 Aug - 11 Aug
Luxury NYC Home Game Room Free Parking
Offices

15. Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is HK$1,130
HK$2,444 total
includes taxes & fees
13 Aug - 14 Aug
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Property grounds

16. Garden Loft with Patios & Green Space · Westchester Retreat

Garden Loft with Patios & Green Space · Westchester Retreat
Scarsdale
9.0 out of 10, Wonderful, (6 reviews)
"It was excellent!! "
United States
Henry C.
The price is HK$1,561
HK$2,826 total
includes taxes & fees
9 Sept - 10 Sept
Garden Loft with Patios & Green Space · Westchester Retreat
TV

17. Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (33 reviews)
"Exactly as described, comfy and close to the Capital and restaurants. We would definitely stay here again.Directions and parking instructions were very clear and helpful."
United States
Sarah W.
The price is HK$1,726
HK$3,239 total
includes taxes & fees
10 Aug - 11 Aug
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Coffee/tea maker, fridge, microwave, oven

18. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (35 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is HK$1,765
HK$3,293 total
includes taxes & fees
10 Aug - 11 Aug
Contemporary Cozy Cottage
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

West Gate Inn Nyack

West Gate Inn Nyack

8/10 Good
"Beds were comfortable. Requested more towels and were immediately delivered. No elevator, so it's a haul to get luggage upstairs. Ice machine in lobby and a little hike to get there. Staff extremely friendly and welcoming. Answered questions completely. Breakfast was included and good. Hit food was just barely warm. Bacon delicious. It is not a new facility and the age shows but it is clean and a great price."
Janae 1-night trip
Posted less than an hour ago
West Gate Inn Nyack

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
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  • 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 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 Rockefeller State Park Preserve 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.