Ossining Vacation Homes

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Ossining holiday homes

NYC-Area Escape Near River, Trails & MTA!

Ossining

Joe W.

HK$6,935 total

includes taxes & fees

14 Jun - 15 Jun

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

Ossining

natalie l.

HK$11,562 total

includes taxes & fees

23 Jun - 24 Jun

Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

HK$13,111 total

includes taxes & fees

23 Jun - 24 Jun

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

Greenwich

Crystal

HK$2,512 total

includes taxes & fees

10 Jun - 11 Jun

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

Carmel Hamlet

Robert T.

HK$3,330 total

includes taxes & fees

3 Jun - 4 Jun

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

Highland Falls

Scott G.

HK$3,048 total

includes taxes & fees

9 Jun - 10 Jun

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Waterside

Sara C.

HK$3,070 total

includes taxes & fees

17 Jun - 18 Jun

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

Southeast Yonkers

Jordan S.

HK$1,057 total

includes taxes & fees

8 Jun - 9 Jun

View all properties

Find holiday rentals that suit your style

Aparthotels

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Ossining Hotel Reviews

La Quinta Inn & Suites by Wyndham Stamford / New York City

4/10 Poor

"La quinta is a great place. However there were too many dogs and the cleanliness was not great. We found feminine hygiene pad near the staircase. Customer service was good."

Royal Hotel Bronx

2/10 Terrible

"I appreciated the convenience of this hotel, but it is not the type of accommodation I would choose to stay at again. The room was very small and uncomfortable, and there was a noticeable urine-like odor. It was clear that the room had not been cleaned thoroughly, as the smell was quite strong. I believe the shower curtains may be the source of the odor and should be replaced. I also had to request that my room be cleaned, which gave me the impression that housekeeping may only service rooms after guests check out. On a positive note, the front desk staff were accommodating and had no issue moving me to a different room when I requested one. The air conditioning, heating, and hot water all worked well. Since I am familiar with the area, parking was not a problem for me; however, guests who are unfamiliar with the neighborhood may find parking frustrating and difficult to navigate."

Hampton Inn & Suites Yonkers

8/10 Good

"The towels were scratchy, and we saw some small ants between our beds on the end tables (rm 430). Other than that it was a nice place to stay. I think the food could be better arranged because I had to ask people to move that were waiting for the waffles so that I could get to the oatmeal. There were a lot of people at breakfast around 7am and no one cleaned the tables before the next group sat down."

Find out more about Ossining