Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
Experiences
Experiences
Services
Services
Start your search
Location
Homes in Ossining
Check in / Check out
Any week
Guests
Add guests
Become a host
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Price filter
Type of place
Type of place filter
Show map
Search results; Over 1,000 homes in Ossining
Over 1,000 homes in Ossining
Photo 1 of 24
Top guest favourite
Guest favourite
Flat in Ossining
Hudson River Peaceful Getaway, Explore from here
2 bedrooms
,
·
2 beds
,
·
1 private bathroom
15–20 Nov
15–20 Nov
$1,924 SGD
Show price breakdown
for 5 nights
$1,924 SGD for 5 nights
,
·
4.96 out of 5 average rating, 559 reviews
4.96 (559)
Photo 1 of 6
Top guest favourite
Guest favourite
Room in Ossining
The hidden gem
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
11–16 Oct
11–16 Oct
$1,209 SGD
$1,062 SGD
Show price breakdown
for 5 nights
Free cancellation
4.99 out of 5 average rating, 79 reviews
4.99 (79)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Ossining
Hudson Valley Fall Escape · 50min to NYC · 3 Acre
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
15–22 Nov
15–22 Nov
$4,552 SGD
Show price breakdown
for 7 nights
$4,552 SGD for 7 nights
Free cancellation
5.0 out of 5 average rating, 20 reviews
5.0 (20)
Photo 1 of 29
Top guest favourite
Guest favourite
Guest suite in Briarcliff Manor
Enjoy Summer Living "Stone Haven" Hudson Valley
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
18–23 Oct
18–23 Oct
$2,502 SGD
$2,196 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 54 reviews
5.0 (54)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Yonkers
Beautiful 2BR jacuzzi & Private Patio
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
8–13 Nov
8–13 Nov
$1,762 SGD
Show price breakdown
for 5 nights
$1,762 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Photo 1 of 20
Guest favourite
Guest favourite
Home in Nyack
Updated Victorian in the heart of Nyack
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
1–6 Apr
1–6 Apr
$2,523 SGD
Show price breakdown
for 5 nights
$2,523 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Photo 1 of 26
Top guest favourite
Guest favourite
Guest suite in Pleasantville
Serene Escape | Private Suite | Ideal for 2
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
8–13 Oct
8–13 Oct
$1,977 SGD
Show price breakdown
for 5 nights
$1,977 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Photo 1 of 29
Home in Croton-on-Hudson
Croton Country House
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
26–31 Oct
26–31 Oct
$4,250 SGD
$3,614 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 29
Top guest favourite
Guest favourite
Villa in Stony Point
Spacious 10BR Escape w/Pool, Hot Tub & Game Room
10 bedrooms
10 bedrooms
,
·
15 beds
15 beds
,
·
4.5 bathrooms
4.5 bathrooms
1–6 Oct
1–6 Oct
$11,334 SGD
$10,019 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Photo 1 of 26
Guest favourite
Guest favourite
Flat in Yonkers
Spacious 3BR Terracotta Retreat with Free Parking!
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
1–6 Nov
1–6 Nov
$1,165 SGD
Show price breakdown
for 5 nights
$1,165 SGD for 5 nights
4.92 out of 5 average rating, 97 reviews
4.92 (97)
Photo 1 of 29
Home in Stony Point
Massive 10BR Estate w/Pool, Hot Tub & Pizza Oven
10 bedrooms
10 bedrooms
,
·
25 beds
25 beds
,
·
9 bathrooms
9 bathrooms
1–6 Oct
1–6 Oct
$12,836 SGD
Show price breakdown
for 5 nights
$12,836 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Photo 1 of 27
Guest favourite
Guest favourite
Townhouse in White Plains
Charming 3BR Home - Quiet Stay, Close to NYC
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
11–16 Oct
11–16 Oct
$2,713 SGD
$2,234 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 143 reviews
4.95 (143)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Highland Falls
Spacious, bright 5 bedroom house near West Point
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
18–23 Oct
18–23 Oct
$3,446 SGD
$3,038 SGD
Show price breakdown
for 5 nights
4.99 out of 5 average rating, 214 reviews
4.99 (214)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Philipstown
Gloves Off Retreat • A Quiet Hudson Valley Escape
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
17–22 Oct
17–22 Oct
$2,506 SGD
$2,279 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Highland Falls
Billy Joel/JP Morgan Hudson Valley Home 1h to NYC
7 bedrooms
7 bedrooms
,
·
21 beds
21 beds
,
·
5 bathrooms
5 bathrooms
1–6 Oct
1–6 Oct
$10,514 SGD
$6,498 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 95 reviews
5.0 (95)
Photo 1 of 20
Guest favourite
Guest favourite
Home in Orangeburg
Matt’s Cozy Quarters Near NYC w/Outdoor Living
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
22–27 Dec
22–27 Dec
$3,593 SGD
Show price breakdown
for 5 nights
$3,593 SGD for 5 nights
Free cancellation
4.8 out of 5 average rating, 15 reviews
4.8 (15)
Photo 1 of 29
Home in Briarcliff Manor
Hudson River Views: Briarcliff Manor Home w/ Deck
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
6 bathrooms
6 bathrooms
28 Nov – 3 Dec
28 Nov – 3 Dec
$8,722 SGD
Show price breakdown
for 5 nights
$8,722 SGD for 5 nights
Free cancellation
Photo 1 of 29
Top guest favourite
Guest favourite
Flat in Croton-on-Hudson
Luxury 2bd⭐Comfort+Style⭐
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
3–8 Nov
3–8 Nov
$1,558 SGD
Show price breakdown
for 5 nights
$1,558 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 386 reviews
4.98 (386)
Photo 1 of 11
Top guest favourite
Guest favourite
Home in Valhalla
Valhalla Home
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$3,523 SGD
Show price breakdown
for 5 nights
$3,523 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 34 reviews
5.0 (34)
1
2
3
4
…
15