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Our top choices for Chappaqua holiday homes
1. 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)
"It's an elegant older house with lots of room for company. Family friendly. The pool was great. My family enjoyed it."
Karen O.
The price is HK$2,667
HK$5,982 total
includes taxes & fees
17 Nov - 18 Nov
2. Summer Pool Oasis Custom Bar Arcade Pool Table
Summer Pool Oasis Custom Bar Arcade Pool TableOssining
The price is HK$3,848
HK$8,004 total
includes taxes & fees
16 Nov - 17 Nov
3. 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, (46 reviews)
"Nice stay"
Christopher J.
The price is HK$1,377
HK$2,564 total
includes taxes & fees
15 Nov - 16 Nov
4. Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Nice Cozy Room By Empire City Casino And Cross County Shopping CenterSoutheast Yonkers
8.0 out of 10, Very good, (20 reviews)
"Great location"
Jordan S.
The price is HK$741
HK$984 total
includes taxes & fees
15 Nov - 16 Nov
5. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
Charming suite with patio, heating, WiFi, free parking in welcoming New RochelleNew Rochelle
10.0 out of 10, Exceptional, (14 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
Drew C.
The price is HK$1,003
HK$2,268 total
includes taxes & fees
16 Nov - 17 Nov
6. Gem by the water+ firepit and all fenced backyard
Gem by the water+ firepit and all fenced backyardWaterside
10.0 out of 10, Exceptional, (22 reviews)
"Property was exactly what we needed for our stay"
Christopher E.
The price is HK$1,759
HK$3,488 total
includes taxes & fees
16 Nov - 17 Nov
7. Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic ViewsGreenwich
10.0 out of 10, Exceptional, (2 reviews)
"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."
Nathan R.
The price is HK$10,967
HK$17,429 total
includes taxes & fees
18 Nov - 19 Nov
8. Spacious 4-bedroom house in northern Westchester with sweeping views
Spacious 4-bedroom house in northern Westchester with sweeping viewsMontrose
The price is HK$3,883
HK$4,827 total
includes taxes & fees
14 Nov - 15 Nov
9. 3BR West Point Retreat-3min to Back Gate+ King Bed
3BR West Point Retreat-3min to Back Gate+ King BedHighland Falls
8.4 out of 10, Very good, (7 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
Christine T.
10. Private Single Fam, walk 2 train/ Theater- Dogs OK
Private Single Fam, walk 2 train/ Theater- Dogs OKGreenwich
The price is HK$1,830
HK$6,043 total
includes taxes & fees
6 Dec - 7 Dec
11. Contemporary Cozy Cottage
Contemporary Cozy CottageLake Peekskill
9.8 out of 10, Exceptional, (43 reviews)
"We’ve actually stayed here twice so that should tell you we enjoy the space and the host is lovely."
Heather M.
The price is HK$1,765
HK$3,033 total
includes taxes & fees
16 Nov - 17 Nov
12. Mansion in Greenwich with private lake and river
Mansion in Greenwich with private lake and riverGreenwich
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful home. Exquisite decor and our kids enjoyed fishing right out back. Thoroughly enjoyed. "
J.J. O.
13. Spacious 3BR Townhome | Garage + Near Downtown
Spacious 3BR Townhome | Garage + Near DowntownWest 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."
Dave J.
The price is HK$2,134
HK$4,113 total
includes taxes & fees
15 Nov - 16 Nov
14. 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. "
Briana T.
The price is HK$1,557
HK$2,782 total
includes taxes & fees
8 Dec - 9 Dec
15. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedroomsLake Peekskill
8.0 out of 10, Very good, (3 reviews)
"This home was just as advertised and perfect for a girls weekend getaway. It was clean, cozy and a picture-perfect fall view. Would highly recommend."
Karen W.
The price is HK$2,601
HK$4,862 total
includes taxes & fees
16 Nov - 17 Nov
16. Perfect 2BR with Free Parking! Walk to West Point!
Perfect 2BR with Free Parking! Walk to West Point!Highland Falls
The price is HK$1,573
HK$2,528 total
includes taxes & fees
16 Nov - 17 Nov
17. Stamford Home | Family, Work and Plenty of Parking
Stamford Home | Family, Work and Plenty of ParkingCove - East Side - Shippan
8.6 out of 10, Excellent, (9 reviews)
"Great location - very spacious and strong AC! host was very communicative and easy to deal with."
Cari B.
The price is HK$1,749
HK$3,691 total
includes taxes & fees
18 Nov - 19 Nov
18. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house. Great location and awesome hosts!"
Robert T.
The price is HK$1,476
HK$2,823 total
includes taxes & fees
15 Nov - 16 Nov
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."
Beth M.
The price is HK$1,656
HK$2,827 total
includes taxes & fees
8 Dec - 9 Dec
20. 5BR Beach House | Water Views + Sauna + Game Room
5BR Beach House | Water Views + Sauna + Game RoomCove - East Side - Shippan
9.4 out of 10, Exceptional, (32 reviews)
"The property was amazing. The house was clean, beautiful, and well equipped. Plenty of space yet still cozy. Host was very communicative and gracious, had a pleasant experience and will definitely be back!"
Maxx V.
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.
Top reviews in Chappaqua
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHGPeekskill
10/10 Excellent
a quiet place to relax in the weekend,not far from west point.On the way to US military academy,you can see tremendous view from the cliff of the mountain.
Zha
