Chappaqua Vacation Homes

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Our top choices for Chappaqua holiday homes

An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

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

Ossining

Karen O.

HK$6,097 total

includes taxes & fees

4 Nov - 5 Nov

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

Ossining

HK$8,006 total

includes taxes & fees

4 Nov - 5 Nov

A dock with kayaks and a canoe, surrounded by trees and a calm lake.

3. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich

Christopher J.

HK$2,610 total

includes taxes & fees

4 Nov - 5 Nov

A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

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

Southeast Yonkers

Jordan S.

HK$910 total

includes taxes & fees

5 Nov - 6 Nov

A square fire pit with flames, surrounded by a wooden deck, set against a backdrop of a lake and trees under a clear sky.

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

Greenwich

Nathan R.

HK$18,412 total

includes taxes & fees

4 Nov - 5 Nov

An outdoor patio with a fire pit, green chairs, and a table.

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

New Rochelle

Drew C.

HK$2,373 total

includes taxes & fees

11 Nov - 12 Nov

An outdoor seating area with a round table, a chair, and a hanging light fixture.

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

Waterside

Christopher E.

HK$3,488 total

includes taxes & fees

9 Nov - 10 Nov

A blue house with a white porch, a welcome sign, and a mailbox.

8. 3BR West Point Retreat-3min to Back Gate+ King Bed

Highland Falls

Christine T.

HK$3,690 total

includes taxes & fees

10 Nov - 11 Nov

A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

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

Highland Falls

James U.

A modern outdoor patio with a seating area, a central table, and a large umbrella.

10. Mansion in Greenwich with private lake and river

Greenwich

J.J. O.

HK$39,465 total

includes taxes & fees

14 Nov - 15 Nov

A modern living room with a white sofa, a glass coffee table, and a piano.

11. Spacious 3BR Townhome | Garage + Near Downtown

West Side

Dave J.

HK$4,260 total

includes taxes & fees

4 Nov - 5 Nov

A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

12. Contemporary Cozy Cottage

Lake Peekskill

Heather M.

HK$3,141 total

includes taxes & fees

4 Nov - 5 Nov

A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

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

Lake Peekskill

Angel R.

HK$4,889 total

includes taxes & fees

4 Nov - 5 Nov

A room with a wooden floor, a white door with a number, and a window with blinds.

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

Highland Falls

Briana T.

HK$2,239 total

includes taxes & fees

4 Nov - 5 Nov

A bedroom with a bed, a bedside table, a window with curtains, a wall clock, and a door.

15. Perfect 2BR with Free Parking! Walk to West Point!

Highland Falls

HK$2,176 total

includes taxes & fees

4 Nov - 5 Nov

A living room with a sofa, armchair, ottoman, and coffee table.

16. Stamford Home | Family, Work and Plenty of Parking

Cove - East Side - Shippan

james w.

HK$3,546 total

includes taxes & fees

4 Nov - 5 Nov

A modern kitchen with granite countertops, a dining area with black chairs, a living room with a sofa and a coffee table, and a large window with a view.

17. 5BR Beach House, Water Views, Steps to Beach, Backyard

Cove - East Side - Shippan

Maxx V.

HK$10,886 total

includes taxes & fees

20 Nov - 21 Nov

A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

18. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Carmel Hamlet

Robert T.

HK$2,931 total

includes taxes & fees

9 Nov - 10 Nov

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!

Highland Falls

Beth M.

HK$2,894 total

includes taxes & fees

1 Dec - 2 Dec

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

20. 5BR Beach Home | Walk to Cove Beach + Private Yard

Cove - East Side - Shippan

Maury A.

HK$7,606 total

includes taxes & fees

5 Nov - 6 Nov

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Top Chappaqua Hotel Reviews

Overlook Lodge at Bear Mountain

10/10 Excellent

"Loooove it"

Hyatt Place New York/Yonkers

8/10 Good

"This is like my tenth time visiting this hotel. I often visit here when I need somewhere to unwind. Each time feels better than the first time. My teenage daughter loves to hang out here, with me and her best friend . There are plenty of stores, restaurants and a movie theater. It is safe so they shop and hang out. “Hyatt we say”!!!!"

Clinton Inn Hotel & Event Center

10/10 Excellent

"The manager Soma was really professional and helpful, I had a little bit of a situation and he helped me resolve it, all the staff members were helpful! The hotel is of course outdated however my room was clean, no issues for me, from what I understand they are renovating"

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