Vacation rentals in Ossining

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Top-rated vacation rentals in Ossining

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Apartment in Mount Kisco

4.93 out of 5 average rating, 147 reviews

Cozy 1 Bdrm Apt; Privt Entry; 5 min walk to train

This cozy apartment is on the lower level of a house, just a 5 minute walk to town and the Harlem Line, Metro North Train stop. A separate entrance to the apt offers complete privacy. This gorgeous space has a fully equipped kitchen, bathroom, comfy twin beds . Located in the adorable town of Mount Kisco, allowing you to take strolls to access restaurants, boutique shops, library, park and bars. It has the feel of a country retreat, a quaint town, and it's an easy commute to White Plains or NYC.

Nov. 13 – 20

$192 CAD per night
Superhost

Home in Ossining

4.84 out of 5 average rating, 124 reviews

Lower Hudson Valley Idyllic Retreat

Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.

Jan. 7 – 14

$600 CAD per night
Guest favourite

Cottage in Cortlandt

4.99 out of 5 average rating, 158 reviews

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

Sep. 11 – 18

$194 CAD per night

Popular amenities for Ossining vacation rentals

Stay near Ossining's top sights

3 Westerly Bar and Grill15 locals recommend
DD's Diner8 locals recommend
Stop & Shop7 locals recommend
The Boathouse23 locals recommend
Los Abuelos Restaurant5 locals recommend
Landmark Diner3 locals recommend

Other great vacation rentals in Ossining

Guest favourite

Guesthouse in Mahopac

4.96 out of 5 average rating, 104 reviews

Sunny Lakeview Guesthouse

Jun. 9 – 16

$196 CAD per night
Guest favourite

Barn in Mount Kisco

4.91 out of 5 average rating, 538 reviews

NY Rustic Cottage Getaway

Jun. 9 – 16

$229 CAD per night
Guest favourite

Guest suite in Stamford

4.93 out of 5 average rating, 110 reviews

Tranquil Retreat in North Stamford

Oct. 6 – 13

$147 CAD per night
Guest favourite

Guesthouse in Suffern

4.91 out of 5 average rating, 110 reviews

Private Studio w/Full Kitchen & Bath

Apr. 6 – 13

$120 CAD per night
Guest favourite

Home in Dobbs Ferry

4.92 out of 5 average rating, 302 reviews

Small cozy room in historic 1828 Dobbs Ferry home.

Dec. 3 – 10

$84 CAD per night
Guest favourite

Cottage in Valhalla

4.97 out of 5 average rating, 218 reviews

Charming private 1BR apt. Easy access to NYC

Jun. 6 – 13

$276 CAD per night
Guest favourite

Bungalow in Hastings-on-Hudson

4.92 out of 5 average rating, 704 reviews

★Tiny House Cottage 35 min to NYC on Hudson River★

Sep. 14 – 21

$230 CAD per night
Guest favourite

Cottage in Cortlandt

5.0 out of 5 average rating, 103 reviews

Cottage at Peekskill Hollow

Jul. 7 – 14

$372 CAD per night
Guest favourite

Cottage in Mohegan Lake

4.93 out of 5 average rating, 167 reviews

The Pearl of Westchester

Sep. 4 – 11

$288 CAD per night
Guest favourite

Guesthouse in Suffern

4.96 out of 5 average rating, 119 reviews

Hiking trails steps from your door!

Sep. 6 – 13

$239 CAD per night
Guest favourite

Guest suite in Tarrytown

4.94 out of 5 average rating, 208 reviews

Brand new private Studio in the heart of Tarrytown

Jun. 14 – 21

$468 CAD per night
Guest favourite

Apartment in Brookfield

4.94 out of 5 average rating, 179 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Nov. 29 – Dec. 6

$198 CAD per night

Quick stats about vacation rentals in Ossining

Total rentals

30 properties

Wifi availability

30 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Rentals with a pool

10 properties have a pool

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

1.5K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Westchester County
  5. Ossining