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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chappaqua holiday homes

A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

1. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
Ossining
8.2 out of 10, Very good, (19 reviews)
"A family trip with teens and tweens- a perfect space! Clean, hist was friendly, the house was stocked with all we'd need! A great getaway for any family NYC trip!"
United States
Justeen P.
The price is HK$1,719
HK$6,197 total
includes taxes & fees
21 Oct - 22 Oct
Snow Days & City Escapes: Spacious Ossining Home
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

2. 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$4,235
HK$8,437 total
includes taxes & fees
3 Nov - 4 Nov
Summer Pool Oasis Custom Bar Arcade Pool Table
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

3. 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, (10 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is HK$4,018
HK$7,602 total
includes taxes & fees
4 Nov - 5 Nov
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

4. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (45 reviews)
"Nice stay"
United States
Christopher J.
The price is HK$1,342
HK$2,736 total
includes taxes & fees
15 Oct - 16 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A room with two beds, white curtains, a ceiling light, and a window with a view.

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

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
White Plains
2.0 out of 10, (1 review)
"This guy is a scammer, an hour before my checkin they finally sent me the "location" and claimed they needed more time to clean the property. Then at 5 pm and hour after they claimed their was a gas leak and I couldn't stay there. Only thing is the address they sent me wasn't real and I am convinced this listing is fake in and used to trick people into staying at their actual property in yonkers. DO NOT RENT FROM THEM!"
United States
Ethan G.
The price is HK$3,885
HK$6,525 total
includes taxes & fees
19 Oct - 20 Oct
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

6. Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
The price is HK$742
HK$1,058 total
includes taxes & fees
18 Oct - 19 Oct
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
A living room with a sofa, a coffee table, a flat-screen TV, a wooden cabinet, and a clock on the wall.

7. Gem by the water+ firepit and all fenced backyard

Gem by the water+ firepit and all fenced backyard
Waterside
10.0 out of 10, Exceptional, (21 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is HK$1,760
HK$4,080 total
includes taxes & fees
15 Oct - 16 Oct
Gem by the water+ firepit and all fenced backyard
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

8. 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 HK$7,063
HK$10,771 total
includes taxes & fees
19 Oct - 20 Oct
Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

9. House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (13 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
The price is HK$1,193
HK$3,442 total
includes taxes & fees
21 Oct - 22 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!
An outdoor patio with a fire pit, green chairs, and a table.

10. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Rochelle
10.0 out of 10, Exceptional, (12 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is HK$1,146
HK$2,765 total
includes taxes & fees
19 Oct - 20 Oct
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
A square fire pit with flames, surrounded by a wooden deck, set against a backdrop of a lake and trees under a clear sky.

11. Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views

Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
Greenwich
10.0 out of 10, Exceptional, (1 review)
"Great location on the lake which the kids loved. The hosts were very friendly and easy to communicate with. The addition of the outdoor grill was a big plus and we enjoyed many afternoons out on the deck. We would stay again."
United States
Nathan R.
The price is HK$11,105
HK$18,406 total
includes taxes & fees
15 Oct - 16 Oct
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
A room with a wooden door, a small table with a vase, and a chair.

12. Spacious 3b/3b Mediterranean in White Plains

Spacious 3b/3b Mediterranean in White Plains
White Plains
9.4 out of 10, Exceptional, (18 reviews)
"This was a wonderful property. It was very charming and had everything we could need. Great neighborhood, lots of room very comfortable. We would definitely stay there again. Great host response!"
United States
Nancy K.
Spacious 3b/3b Mediterranean in White Plains
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

13. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (41 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$1,766
HK$3,312 total
includes taxes & fees
19 Oct - 20 Oct
Contemporary Cozy Cottage
A modern living room with a white sofa, a glass coffee table, and a piano.

14. Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
West Side
9.2 out of 10, Wonderful, (9 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
The price is HK$2,888
HK$5,429 total
includes taxes & fees
28 Oct - 29 Oct
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

15. Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Great location and super host. "
United States
James U.
The price is HK$1,256
HK$3,769 total
includes taxes & fees
2 Nov - 3 Nov
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

16. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
10.0 out of 10, Exceptional, (1 review)
"We had an amazing stay at the lake house. The home is beautiful inside and out, and there is every amenity you could think of, from cooking and cleaning supplies to extra towels and blankets. The view of the lake is stunning and we enjoyed the peace and quiet of the little community. Linh is an excellent host and helped answer all of our questions. We will definitely be back!"
United States
Angel R.
The price is HK$2,602
HK$5,167 total
includes taxes & fees
21 Oct - 22 Oct
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A room with a wooden floor, a white door with a number, and a window with blinds.

17. Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is HK$1,492
HK$2,840 total
includes taxes & fees
20 Oct - 21 Oct
Lovely 3BR Home with parking-Walk to WP Gate!
A living room with a sofa set, a coffee table, and a television on a stand.

18. Spacious Stamford Home | Family, Work, Parking

Spacious Stamford Home | Family, Work, Parking
Cove - East Side - Shippan
8.6 out of 10, Excellent, (9 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is HK$2,456
HK$4,771 total
includes taxes & fees
27 Oct - 28 Oct
Spacious Stamford Home | Family, Work, Parking
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

19. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
The price is HK$2,076
HK$3,532 total
includes taxes & fees
2 Nov - 3 Nov
Fabulous 3bdrm Home w/parking!
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

Hyatt Regency Greenwich

Hyatt Regency Greenwich

8/10 Good
"The property is very pretty. Unfortunately the greenhouse style ceiling in the lobby was leaking due to heavy rain. The rooms were clean but the bathroom needs some work. Not quite clean enough for my standards. It needs some freshening up. The staff is friendly. Breakfast was ok but the staff seems to need more training to meet the standards of this type of hotel."
Robert 2-night trip
Posted 21 hours ago
Hyatt Regency Greenwich

Find out more about Chappaqua

Chappaqua Vacation Homes information

Number of reviews
247
Accommodation
236 Vacation Homes
Lowest Price
HK$1,058
Highest Price
HK$18,406

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