Ossining Vacation Homes

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Our top choices for Ossining holiday homes

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

Ossining

natalie l.

HK$11,559 total

includes taxes & fees

28 May - 29 May

Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

HK$11,242 total

includes taxes & fees

28 May - 29 May

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

Highland Falls

Scott G.

HK$2,471 total

includes taxes & fees

25 May - 26 May

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

Greenwich

Crystal

HK$2,528 total

includes taxes & fees

25 May - 26 May

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

Southeast Yonkers

Jordan S.

HK$1,057 total

includes taxes & fees

26 May - 27 May

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

Waterside

Sara C.

HK$2,723 total

includes taxes & fees

1 Jun - 2 Jun

Cheerful Home in Yonkers NY

Lincoln Park

Tanya J.

HK$4,622 total

includes taxes & fees

25 May - 26 May

Stamford : The Comfy Cove Hideout

Cove - East Side - Shippan

HK$2,208 total

includes taxes & fees

28 May - 29 May

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Top Ossining Hotel Reviews

LIV Hotel Bronx - Newly Built

10/10 Excellent

"Did Good, everything you ask for my room was amazing wouldnt even lie"

HYATT house White Plains

10/10 Excellent

"The women at the front desk at night were amazing!!! We were so tired from traveling from Florida. My parents are 83 and have trouble getting around. We came for my son’s college graduation, and the woman immediately upgraded our room. She also gave us vouchers for the restaurant, which we ended up using. The bartender was nice too. I asked if they had a steamer for my son’s cap and gown and suit, which had gotten wrinkled in travel. They had one! The room was amazing— the only thing was the stove did not work. Everything else was great, though. The beds were so comfy!!! The pool is nice too. We just loved our stay. I had never stayed at a Hyatt House before. Always stayed at a Residence Inn or Homewood Suites, but I am a convert now. It was also close to the holy grail of grocery stores, Wegmans! We got plenty of meals and snacks that only required a microwave. It’s in a safe area too. Everything for my son’s graduation was just perfect thanks to your lovely, kind and helpful front desk staff. Those ladies rock!!! Thank you so very much!!"

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