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Search results; Over 1,000 homes in Chappaqua

Guest favourite
Tiny home in Chappaqua
Cozy tiny log cabin on 13 acres
1 bedroom, 1 bed, 1 bathroom
21–26 Sept
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4.89 out of 5 average rating, 70 reviews
Top guest favourite
Home in Mount Kisco
Serene Retreat in the Hills w/Jacuzzi
4 bedrooms, 4 beds, 2 bathrooms
13–18 Oct
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Guest suite in Pleasantville
Serene Escape | Private Suite | Ideal for 2
1 bedroom, 1 queen bed, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Mount Kisco
Incredible barn in country setting
2 bedrooms, 2 beds, 1 bathroom
15–20 Sept
4.94 out of 5 average rating, 160 reviews
Home in Sleepy Hollow
Charming River Town Stay by the Hudson
4 bedrooms, 6 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Townhouse in White Plains
Charming 3BR Home - Quiet Stay, Close to NYC
3 bedrooms, 4 beds, 1 bathroom
11–16 Oct
4.95 out of 5 average rating, 142 reviews
Top guest favourite
Home in Valhalla
Valhalla Home
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Bedford
Comfortable Mid-Century on Quiet Country Road
4 bedrooms, 5 beds, 2 bathrooms
27 Oct – 1 Nov
5.0 out of 5 average rating, 79 reviews
Top guest favourite
Guest suite in Briarcliff Manor
Enjoy Summer Living "Stone Haven" Hudson Valley
1 bedroom, 2 beds, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 54 reviews
Guest favourite
Rooms in Bedford Hills
The Creative Escapade
3 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.85 out of 5 average rating, 34 reviews
Top guest favourite
Home in Pleasantville
Charming 3BR Walk to Town & Train
3 bedrooms, 4 beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Katonah
Elegant Hideaway: Cozy Cottage in Katonah, NY
1 bedroom, 1 queen bed, 1 bathroom
1–7 Oct
5.0 out of 5 average rating, 12 reviews
Home in Pleasantville
Cheerful home downtown Pleasantville
3 bedrooms, 3 beds, 2.5 bathrooms
21–26 Nov
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Katonah
Peace and Stunning Views in Katonah
3 bedrooms, 3 queen beds, 2 bathrooms
26–31 Oct
4.93 out of 5 average rating, 111 reviews
Top guest favourite
Home in Redding
Retreat with Heated Pool, 1 Mile to NYC Train
4 bedrooms, 5 beds, 2.5 bathrooms
4–9 Oct
4.99 out of 5 average rating, 107 reviews
Home in Yonkers
Beautiful 2BR jacuzzi & Private Patio
2 bedrooms, 4 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest suite in Croton-on-Hudson
Forest Suite | Croton Dam Trails | 45 Min NYC
1 bedroom, 2 beds, 2 bathrooms
27 Sept – 2 Oct
4.91 out of 5 average rating, 65 reviews
Guest favourite
Home in Bedford
Chancton House | 4 Bedrooms | Pool | Bedford
4 bedrooms, 5 beds, 4.5 bathrooms
28 Sept – 3 Oct
4.92 out of 5 average rating, 26 reviews
Guest favourite
Home in Bedford
Bedford Paradise Getaway | Hot Tub | Town Center
3 bedrooms, 4 beds, 2.5 bathrooms
12–17 Oct
4.92 out of 5 average rating, 119 reviews