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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$2,885
HK$6,222 total
includes taxes & fees
16 Nov - 17 Nov
2. Summer Pool Oasis Custom Bar Arcade Pool Table
Summer Pool Oasis Custom Bar Arcade Pool TableOssining
The price is HK$4,086
HK$8,267 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$1,376
HK$2,649 total
includes taxes & fees
11 Nov - 12 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$983 total
includes taxes & fees
15 Nov - 16 Nov
5. 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$15,680
HK$23,245 total
includes taxes & fees
16 Nov - 17 Nov
6. 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$1,002
HK$2,455 total
includes taxes & fees
16 Nov - 17 Nov
7. Gem by the water+ firepit and all fenced backyard
Gem by the water+ firepit and all fenced backyardWaterside
10.0 out of 10, Exceptional, (21 reviews)
"Property was exactly what we needed for our stay"
Christopher E.
The price is HK$1,758
HK$3,486 total
includes taxes & fees
20 Nov - 21 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$3,882
HK$4,826 total
includes taxes & fees
12 Nov - 13 Nov
9. 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.
The price is HK$30,979
HK$41,125 total
includes taxes & fees
14 Nov - 15 Nov
10. 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$2,360
HK$4,529 total
includes taxes & fees
11 Nov - 12 Nov
11. Perfect 2BR with Free Parking! Walk to West Point!
Perfect 2BR with Free Parking! Walk to West Point!Highland Falls
The price is HK$1,115
HK$2,070 total
includes taxes & fees
11 Nov - 12 Nov
12. 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$1,764
HK$3,138 total
includes taxes & fees
11 Nov - 12 Nov
13. 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.
The price is HK$1,043
HK$3,588 total
includes taxes & fees
11 Nov - 12 Nov
14. 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$2,891
HK$5,233 total
includes taxes & fees
16 Nov - 17 Nov
15. 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$1,556
HK$2,781 total
includes taxes & fees
8 Dec - 9 Dec
16. 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$1,208
HK$2,275 total
includes taxes & fees
11 Nov - 12 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)
"the home was nice clean if in the area I would stay here again"
james w.
The price is HK$1,504
HK$3,384 total
includes taxes & fees
11 Nov - 12 Nov
18. 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.
The price is HK$3,481
HK$6,847 total
includes taxes & fees
15 Nov - 16 Nov
19. Hudson Valley/West Point Retreat w/ parking!
Hudson Valley/West Point Retreat w/ parking!Highland Falls
The price is HK$1,289
HK$2,441 total
includes taxes & fees
11 Nov - 12 Nov
20. 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$1,383
HK$2,612 total
includes taxes & fees
12 Nov - 13 Nov
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
