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Ossining Vacation Rentals

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Tonight
Nov 18 - Nov 19
Tomorrow
Nov 19 - Nov 20
This weekend
Nov 21 - Nov 23
Next weekend
Nov 28 - Nov 30

Vacation Rentals in Ossining

Interior
1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss

2.0 star property
Ossining
The price is ￥43,320
￥57,712 total
includes taxes & fees
Nov 24 - Nov 25
1BR Queen near NYC | Trails, Biking & Sauna Bliss
Interior
Near NYC! | Stylish Guestroom

Near NYC! | Stylish Guestroom

2.0 star property
Ossining
The price is ￥47,047
￥60,054 total
includes taxes & fees
Nov 24 - Nov 25
Near NYC! | Stylish Guestroom
Interior
Polished 1BR w/ Accessible Room Features + Sauna

Polished 1BR w/ Accessible Room Features + Sauna

2.0 star property
Ossining
The price is ￥43,320
￥57,530 total
includes taxes & fees
Nov 25 - Nov 26
Polished 1BR w/ Accessible Room Features + Sauna
Lobby
Stamford Suites

Stamford Suites

4.0 star property
Downtown Stamford
6.2 out of 10, (73)
"It was great"
United States
Natalie
The price is ￥18,871
￥21,702 total
includes taxes & fees
Nov 20 - Nov 21
Stamford Suites
Terrace/patio
3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room

2.0 star property
Southeast Yonkers
8.0 out of 10, Very Good, (1)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
United States
Anonymous traveler
The price is ￥90,217
￥116,303 total
includes taxes & fees
Nov 20 - Nov 21
3BR Prime Luxury near NYC w Arcade Room
Lounge
Luxury Apartments by Hyatus at The Asher

Luxury Apartments by Hyatus at The Asher

4.5 star property
Downtown Stamford
10.0 out of 10, Exceptional, (19)
"Clean and had everything you need for longer stay Comfortable "
United States
christine
Luxury Apartments by Hyatus at The Asher
Reception
Global Luxury Suites White Plains

Global Luxury Suites White Plains

3.5 star property
White Plains
6.8 out of 10, (33)
"Being in an apartment building for an actual stay instead of a house was a first for myself and the family but overall a good stay."
United States
Ramon
Global Luxury Suites White Plains
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Greenwich
9.6 out of 10, Exceptional, (21)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
The price is ￥15,511
￥36,005 total
includes taxes & fees
Nov 24 - Nov 25
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Smart TV
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

Bronx
10.0 out of 10, Exceptional, (12)
"Everything was very clean and cozy.We have enjoyed our stay there. "
United States
LORAINE L.
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC
2 bedrooms, in-room safe, WiFi
Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC

Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC

Bronx
9.0 out of 10, Wonderful, (8)
"We really enjoyed our stay at this apartment. It was very spacious and nice. The only small thing they needed to add was a bath mat for the tub, it was very slippery, and maybe a small step stool for shorter people to reach some items in the cupboard. I'm only 5'4". Other than that, we had an excellent stay. We did get to meet the owner, because we initially had trouble getting into the apartment and he was a very friendly person. The neighborhood was very nice and clean, would definitely...
United States
Eddie S.
Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC
Fridge, microwave, oven, stovetop
Marvelous 5-bedroom house with AC in Yonkers

Marvelous 5-bedroom house with AC in Yonkers

2.0 star property
Bryn Mawr
2.0 out of 10, (1)
"Cancelled my stay at check out time while I was at the NY airport— said there was a “power outage”. “Upgraded” me to a luxury property that turned out to be a dirty 3rd floor walk up. When I asked for a refund, they lied to VRBO and said I never showed up. I had to prove to VRBO with texts and phone records that they cancelled me. I suspected a bait and switch. Also, VRBO had to start an investigation because the phone number from the owner was an unknown number—my information had been...
United States
Amy L.
Marvelous 5-bedroom house with AC in Yonkers
House | Living area
Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking

3.0 star property
Southeast Yonkers
7.2 out of 10, Good, (5)
"This was an excellent House My birthday weekend was amazing I totally would book again"
United States
Keisheena
Modern Luxury Home w GameRoom & Parking
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery
9.8 out of 10, Exceptional, (127)
"It has an incredible mountain and water view. "
United States
MIHYUN
The price is ￥29,191
￥47,601 total
includes taxes & fees
Nov 23 - Nov 24
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
5 bedrooms, in-room safe, desk, iron/ironing board
NJ New Construction Luxury Home - Minutes to NYC - Vacation or Staycation

NJ New Construction Luxury Home - Minutes to NYC - Vacation or Staycation

2.0 star property
River Edge
7.6 out of 10, Good, (5)
"The stay was great. The host Kris is very communicative and easily accessible by text. The house was kept very clean and the amenities were great for our party. Would definitely visit again. "
United States
Abhi M.
The price is ￥232,905
￥291,937 total
includes taxes & fees
Nov 20 - Nov 21
NJ New Construction Luxury Home - Minutes to NYC - Vacation or Staycation
Living area
Luxury NY Home close to NYC

Luxury NY Home close to NYC

2.0 star property
Southeast Yonkers
Luxury NY Home close to NYC
Smart TV
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

Scarsdale
9.0 out of 10, Wonderful, (4)
"Space was clean, nice, and hosts were very helpful and communicative."
United States
Steven C.
The price is ￥26,396
￥50,613 total
includes taxes & fees
Nov 23 - Nov 24
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic
1 bedroom, iron/ironing board, free WiFi, bed sheets
Elegant Hideaway • Free Parking

Elegant Hideaway • Free Parking

White Plains
10.0 out of 10, Exceptional, (1)
"This location was tranquil and close to everything I expected for meals and entertainment. Easy to get to and felt warm and inviting. Fayeem was responsive and helpful towards my requests. I look forward to staying here again. Thank you!"
United States
Moses A.
Elegant Hideaway • Free Parking
In-room dining
Luxury Living in the Heart of NY

Luxury Living in the Heart of NY

4.0 star property
Southeast Yonkers
2.0 out of 10, (1)
"The photos of the unit were beautiful however the wear and tear on the actual property did not compare. The bathroom sink constantly leaked and because the floors were not even they stayed wet. The nightstands were broken the refrigerator would not open all the way. I also was not notified until the day of check in that the unit was on the 3rd floor and there was 2 flights of stairs just to get to the entrance to the unit."
United States
Ebony
Luxury Living in the Heart of NY
Luxury House | Private kitchen | Full-size fridge, microwave, oven, stovetop
Luxury NY Home with Free Parking

Luxury NY Home with Free Parking

4.0 star property
White Plains
8.0 out of 10, Very Good, (1)
"Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine. "
United States
Safiya
Luxury NY Home with Free Parking
Outdoor dining
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

Croton-on-Hudson
9.6 out of 10, Exceptional, (15)
"We enjoyed our overnight stay at this quaint nicely appointed carriage house."
United States
Cathleen C.
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ossining Hotel Reviews

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

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

10/10 Excellent
"Yes"
Oxana 2-night trip
Posted 10 hours ago
La Quinta Inn & Suites by Wyndham Stamford / New York City

Find out more about Ossining

Search for holiday rentals in Ossining on Expedia! You can easily find your home rentals, villas, holiday apartments in Ossining using one of the methods below:

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Look no further and take a look at our great range of rental properties in Ossining!

Frequently asked questions

Can I find a vacation rental in Ossining?

Yes, there are vacation rentals close to well known attractions in Ossining, or you can go with a more remote option if you're looking for a relaxing stay. Ossining is known for its restaurants and parks. Make sure you have time to check out the golf courses and university setting during your trip.

What's the top vacation rental that Ossining has to offer?

3BR Prime Luxury near NYC w Arcade Room: You might want to consider this vacation home rental near Ossining, which is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals will I find in Ossining?

With 7 Expedia vacation rentals, you're sure to find just the right place for your Ossining stay.

What’s there to see and do in Ossining?

Cultural attractions include Ossining Historical Society and Sing Sing Prison Museum, whereas Teatown Lake Reservation and Kitchawan Preserve are a couple of picturesque spots to enjoy the outdoors. Sing Sing Correctional Facility and Thomas J. Watson Research Center are other places to visit while you're in town.

What’s a vacation rental in Ossining like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Ossining. Vacation rentals feature extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for families.