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Chappaqua Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Chappaqua vacation rentals

Luxury Apartment | Private kitchen

1. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is AED 658
AED 1,300 total
includes taxes & fees
15 Aug - 16 Aug
Elegant Hideaway with Free Parking
Property grounds

2. 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
8.0 out of 10, Very Good, (5 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 AED 621
AED 840 total
includes taxes & fees
12 Sep - 13 Sep
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Smart TV, video games, DVD player, books

3. '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 AED 987
AED 1,784 total
includes taxes & fees
24 Aug - 25 Aug
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Apartment (1 Bedroom) | Interior

4. 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 AED 522
AED 1,065 total
includes taxes & fees
17 Aug - 18 Aug
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
House | 5 bedrooms

5. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is AED 2,676
AED 4,721 total
includes taxes & fees
1 Sep - 2 Sep
Summer Pool Oasis Custom Bar Arcade Pool Table
Interior

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

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is AED 790
AED 1,006 total
includes taxes & fees
16 Aug - 17 Aug
1BR Queen near NYC | Trails, Biking & Sauna Bliss
Villa, Garden View | Living area

7. 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 AED 1,818
AED 2,627 total
includes taxes & fees
15 Aug - 16 Aug
Luxury NYC Home Game Room Free Parking
Outdoor banquet area

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

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (9 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is AED 2,479
AED 4,436 total
includes taxes & fees
1 Sep - 2 Sep
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
3 bedrooms, iron/ironing board, internet, bed sheets

9. 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 AED 926
AED 1,932 total
includes taxes & fees
16 Aug - 17 Aug
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
Property grounds

10. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (20 reviews)
"Great place to stay! "
United States
Megan D.
The price is AED 441
AED 761 total
includes taxes & fees
7 Sep - 8 Sep
Piermont Oasis
Luxury Villa, Garden View | Dining

11. 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 AED 1,488
AED 2,314 total
includes taxes & fees
15 Aug - 16 Aug
Luxury NYC Home with Free Parking for 12
Living area

12. Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC

Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
White Plains
2.0 out of 10, (1 review)
"An hour before check-in we were called by the property manager, after four days of messaging them through the app without response, to advise us that the property had an alleged water pipe burst and was unavailable, then attempted to upcharge us for alternate accommodations. An alternate place to stay was finally provided at no additional charge but much smaller than what had been booked. Given the absence of communication for four days and then a sudden incident the day of check-in - the day...
United States
James D.
The price is AED 3,306
AED 5,037 total
includes taxes & fees
15 Aug - 16 Aug
Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
Property grounds

13. 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 AED 738
AED 1,348 total
includes taxes & fees
8 Sep - 9 Sep
Garden Loft with Patios & Green Space · Westchester Retreat
Coffee/tea maker, fridge, microwave, oven

14. 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 AED 826
AED 1,563 total
includes taxes & fees
17 Aug - 18 Aug
Contemporary Cozy Cottage
Coffee/tea maker, fridge, microwave, oven

15. Private Country Getaway

Private Country Getaway
Bedford Hills
9.6 out of 10, Exceptional, (4 reviews)
"We had a busy and lovely weekend to attend and be part of my nieces wedding. The location was perfect and the property is beautiful. Kitchen was perfect for gathering in the morning and the great room was big and comfy for catching up! "
United States
Karin R.
The price is AED 2,755
AED 5,187 total
includes taxes & fees
24 Aug - 25 Aug
Private Country Getaway
Offices

16. 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 AED 529
AED 1,137 total
includes taxes & fees
16 Aug - 17 Aug
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
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 AED 808
AED 1,479 total
includes taxes & fees
18 Aug - 19 Aug
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
TV

18. 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 AED 536
AED 963 total
includes taxes & fees
14 Sep - 15 Sep
Cozy 1-bedroom retreat minutes from West Point!
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

LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

10/10 Excellent
"Clean room, good working a/c, nice tv"
brooke 1-night trip
Posted 3 hours ago
LIV Hotel Bronx - Newly Built

Frequently asked questions

Can I find a vacation rental in Chappaqua?

Yes, we offer vacation rentals in Chappaqua near Chappaqua Performing Arts Center, or you can select a more secluded option if you want a relaxing stay. Our travelers 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 vacation home rentals in Chappaqua?

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: This vacation home rental near Chappaqua is located next to a golf course and has a balcony, a barbecue grill, 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like foosball.

How many vacation rentals will I find in Chappaqua?

Expedia has 3 vacation 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 larger area.

What’s a vacation rental in Chappaqua like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Chappaqua. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a family getaway.