Chappaqua Vacation Homes

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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

Ossining

Justeen P.

HK$6,197 total

includes taxes & fees

21 Oct - 22 Oct

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$8,201 total

includes taxes & fees

3 Nov - 4 Nov

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!

Ossining

natalie l.

HK$7,602 total

includes taxes & fees

9 Nov - 10 Nov

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.

Greenwich

Christopher J.

HK$2,908 total

includes taxes & fees

15 Nov - 16 Nov

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

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

Southeast Yonkers

Jordan S.

HK$1,058 total

includes taxes & fees

19 Oct - 20 Oct

A room with two beds, white curtains, a ceiling light, and a window with a view.

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

White Plains

"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!"

Ethan G.

HK$6,526 total

includes taxes & fees

19 Oct - 20 Oct

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.

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

White Plains

"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...

James D.

HK$10,772 total

includes taxes & fees

19 Oct - 20 Oct

A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

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

Highland Falls

Leann M.

HK$3,173 total

includes taxes & fees

20 Oct - 21 Oct

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

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

Greenwich

Nathan R.

HK$19,102 total

includes taxes & fees

20 Oct - 21 Oct

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

New Rochelle

Drew C.

HK$2,756 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.

11. Fabulous 3bdrm Home w/parking!

Highland Falls

Beth M.

HK$3,182 total

includes taxes & fees

17 Nov - 18 Nov

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

12. Contemporary Cozy Cottage

Lake Peekskill

Aj L.

HK$3,312 total

includes taxes & fees

19 Oct - 20 Oct

A bedroom with a bed, bedside tables, a mirror, a wardrobe, and a painting on the wall.

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

Waterside

Leslie S.

HK$3,662 total

includes taxes & fees

20 Oct - 21 Oct

A room with a wooden door, a small table with a vase, and a chair.

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

White Plains

Nancy K.

HK$6,950 total

includes taxes & fees

22 Oct - 23 Oct

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

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

West Side

Dave J.

HK$5,598 total

includes taxes & fees

27 Oct - 28 Oct

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

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

Highland Falls

James U.

HK$3,769 total

includes taxes & fees

2 Nov - 3 Nov

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

17. Mansion in Greenwich with private lake and river

Greenwich

J.J. O.

HK$41,915 total

includes taxes & fees

14 Nov - 15 Nov

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

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

Highland Falls

Briana T.

HK$3,105 total

includes taxes & fees

17 Nov - 18 Nov

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

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

Lake Peekskill

Angel R.

HK$5,168 total

includes taxes & fees

21 Oct - 22 Oct

A living room with a sofa set, a coffee table, and a television on a stand.

20. Spacious Stamford Home | Family, Work, Parking

Cove - East Side - Shippan

james w.

HK$4,300 total

includes taxes & fees

26 Oct - 27 Oct

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Top Chappaqua Hotel Reviews

Westchester Marriott

8/10 Good

"C"

Ardsley Acres Hotel Westchester

10/10 Excellent

"Don't judge a book by it's cover. The hotel is undergoing renovations and beautification. When we pulled up we weren't sure about it, because it looks very dated. The hotel manager apologized for their appearance and told us about the renovations. We stayed in room 15 and it was a lovely modern remodel. The room was spotlessly clean, the bed was new with a variety of pillows. Bathroom was also spotless. Room darkening shades made it perfect for our afternoon nap. There's a large fridge, iron and ironing board, new TV with streaming access. The view of the trees while turning were beautiful. It was quiet and we had a good sleep. The shower was hot with good water pressure. Whoever installed the dimming light switch deserves a raise cause it was great in the morning. The outside signage may throw you off but this is a hidden gem. Will definitely stay again."

Overlook Lodge at Bear Mountain

10/10 Excellent

"Bear Mountain Inn is a unique and beautiful retreat in the heart of the Hudson Valley. We go for the scenery, hiking, and watching the marine and rail traffic along the Hudson River. Staff is always helpful. We booked 2 nights but could only. stay 1 due to a family emergency and the staff worked with Expedia to refund the 2nd night. Will definitely return as we love the atmosphere. Stayed in 1 of the stone cottages in the woods above the lake. Basic room with a shared common area and outdoor porch/deck. Room had a small refrigerator and TV with local channels. Clean and quiet and what you'd expect in a state or national park setting. Great 1.5 mile paved walking trail below the cottage that circles the picturesque lake on the property grounds. Nice way to start the day."

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