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Ossining Vacation Rentals

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Vacation Rentals in Ossining

Stamford Suites
Exterior
Stamford Suites
2.5 star property
6.8 out of 10, (719)
"super nice people there "
The price is CA $207
CA $239 total
includes taxes & fees
Jun 19 - Jun 20
Stamford Suites
Waterfront Retreat Center for Health & Wellness
Exterior
Waterfront Retreat Center for Health & Wellness
9.6 out of 10, Exceptional, (50)
"We stayed at the New Dawn for a Memorial Service. The setting on the water was so peaceful and private, yet easy access for those of us traveling by public transportation from Manhattan and La Guardia airport. We had chairs lined up facing the water for a Celebration of Life Ceremony. The whole downstairs layout was just wonderful with indoor and outdoor areas for people to gather, sharing memories and grief. Food platters from Costco were easily arranged and the weather was perfect. It was so...
Waterfront Retreat Center for Health & Wellness
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is CA $277
CA $390 total
includes taxes & fees
Jun 5 - Jun 6
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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Spacious 3BR Private Home * Direct Water View
Exterior
Spacious 3BR Private Home * Direct Water View
10.0 out of 10, Exceptional, (12)
"This is a very nice accommodation. Situated by the beautiful park and water. You can find shopping facilities within walking distance. The landlord was very reliable in making sure that our stay was very nice."
Spacious 3BR Private Home * Direct Water View
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
1 bedroom, desk, iron/ironing board, travel crib
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
Interior
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
10.0 out of 10, Exceptional, (3)
"7 bedrooms, most with water views, were perfect for my siblings and me, our spouses and children, and our mother to spend a glorious weekend together! We hosted an unforgettable 80th bday party for our Mom with all our extended family and friends. Wow! The house is gorgeous! It is perfect for a event. The grand hall, the ability to open up the rooms to the backyard, and the VIEW, truly set the stage for a beautiful evening. The home is truly remarkable! My mom was overwhelmed and so thankful...
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Terrace/patio
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (104)
"Neighborhood great for walking dogs. Would have loved a sink besides bathroom. Overall great value."
Lower Lvl Private 2BR/1BA Family/Pet Friendly
The Subterranean Haven
Exterior
The Subterranean Haven
10.0 out of 10, Exceptional, (1)
"The neighborhood is really nice and clean with a good variety of stores nearby. We found the subterranean haven to be a great location for unwinding and having small events. The George's are incredibly understanding, patient and flexible. We'd definitely recommend this host to anyone."
The price is CA $245
CA $279 total
includes taxes & fees
Jun 11 - Jun 12
The Subterranean Haven
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions
Outdoor dining
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions
9.6 out of 10, Exceptional, (44)
"We had a great time celebrating Thanksgiving with our adult children in the Carriage house. The location was great - beautiful neighborhood in small town with easy access to all the things we did in NYC. Lisa helped us when we didn’t have all the right kitchen tools for our meal and worked with us on our schedule for her dog business. It was a real pleasure spending our special family time in this home - comfortable and so many things to do (we played ping pong and pool). Thank you Lisa for a...
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Serenity@46, Spacious Home with Beautiful Gathering Spaces & Split Bedroom Wings
Fridge, microwave, oven, stovetop
Serenity@46, Spacious Home with Beautiful Gathering Spaces & Split Bedroom Wings
10.0 out of 10, Exceptional, (6)
"The house is as beautiful as all the pictures, if not better. It was spotless and absolutely beautiful! And Leen was an amazing host. She walked you through everything and even though she has a 6 hour time difference from the home she is readily available to help with any questions and also has people close by if there is a need (which of course there wasn’t!). My family and I had an amazing time while there! Definitely stay here! You won’t be disappointed!!!"
Serenity@46, Spacious Home with Beautiful Gathering Spaces & Split Bedroom Wings
Global Luxury Suites White Plains
Reception
Global Luxury Suites White Plains
3.5 star property
7.6 out of 10, Good, (17)
"If this option is available in the city you are traveling to, take it! You get a home-y, modern APARTMENT with space, rather than a tiny, old hotel room. I always search Global Luxury Suites before searching anything else."
Global Luxury Suites White Plains
Cozy Spacious Guest Suite 15 minutes from NYC
Interior
Cozy Spacious Guest Suite 15 minutes from NYC
6.8 out of 10, (3)
"Quiet neighborhood ample room to relax."
The price is CA $123
CA $225 total
includes taxes & fees
Jun 6 - Jun 7
Cozy Spacious Guest Suite 15 minutes from NYC
Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor
Fridge, microwave, oven, stovetop
Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor
10.0 out of 10, Exceptional, (1)
"The owner is a verry nice person!!"
Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor
Stylish 3-bedroom 3rd fl Apt in Mount Vernon, NY
Smart TV
Stylish 3-bedroom 3rd fl Apt in Mount Vernon, NY
9.4 out of 10, Exceptional, (9)
"The apartment was exactly as stated and shown in the photos"
Stylish 3-bedroom 3rd fl Apt in Mount Vernon, NY
Mini Garden-Apartment near New York City
Interior
Mini Garden-Apartment near New York City
Mini Garden-Apartment near New York City
Serenity Awaits at this Cozy Lakeside Bungalow
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (18)
"My husband, dog and I had a great Memorial Day weekend at this lakeside property. The house is a short drive away from NYC and is situated perfectly between the quaint towns of Ridgefield and Katonah. We had a good time enjoying the lake and nearby hikes."
Serenity Awaits at this Cozy Lakeside Bungalow
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Bathroom
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (62)
"Stayed for West Point graduation. Beautiful home, scenic views, and everything we needed."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
3 bedrooms, iron/ironing board, WiFi, bed sheets
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, (1)
"We went to the area to celebrate my husbands 30th birthday with some friends and absolutely loved the home. It was brand new and decorated immaculately. It comfortably fit our group and we thoroughly enjoyed our time there. The hosts were super accommodating and quick to respond. Would absolutely reccomend and go again!"
The price is CA $680
CA $1,248 total
includes taxes & fees
Jun 10 - Jun 11
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Basement Apartment Close to Bus & Metro-North
Interior
Basement Apartment Close to Bus & Metro-North
The price is CA $143
CA $204 total
includes taxes & fees
Jun 6 - Jun 7
Basement Apartment Close to Bus & Metro-North
Don't see what you're looking for?
See all available properties in Ossining
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.

Ossining Vacation Rental Travel Info

Number of vacation rentals
3
Popular accommodation
Ossining private vacation homes
Known landmarks
Franklin D. Roosevelt State Park, Paramount Hudson Valley Theater and Rockefeller Archive Center
International airports
New York, NY (JFK-John F. Kennedy Intl.) and New York, NY (LGA-LaGuardia)

Other types of properties in Ossining you may be interested in

Armoni Inn & Suites
Restaurant
Armoni Inn & Suites
3.5 star property
6.2 out of 10, (1194)
"There was a very load noise coming from the bathroom pipes almost like jack hammering "
The price is CA $103
CA $115 total
includes taxes & fees
Jun 23 - Jun 24
Armoni Inn & Suites
Royal Regency Hotel
Interior
Royal Regency Hotel
3.5 star property
8.0 out of 10, Very good, (1508)
"We were very impressed with this property as we needed a place to stay for one night. Our room was beautiful and very clean. Our one sticking point is that there is a restaurant under the hotel. The restaurant has live music on the weekends and the music was so loud it came up through our room on the first floor until 1am. Calling the hotel desk did nothing to mitigate the situation as the restaurant is not owned by the same folks. The hotel has a sign in its elevator stating that "Quiet time is...
The price is CA $232
CA $292 total
includes taxes & fees
Jun 13 - Jun 14
Royal Regency Hotel
Amsterdam Hotel
Front of property
Amsterdam Hotel
2.0 star property
8.4 out of 10, Very good, (1516)
"THIS IS MY GO TO HOTEL WHEN I WORK IN THE AREA WHICH IS ABOUT 7 0R 8 TIMES A YEAR. I HAVE BEEN USING THIS HOTEL ABOUT 10 YEARS AND LIKE IT VERY MUCH. IT IS CLEAN, QUIET& COMFORTABLE. THE DESK STAFF KNOWS ME SOMEWHAT SO IT'S NICE WHEN I ARRIVE TO BE ADDRESSED BY NAME. THE ENTIRE STAFF IS VERY FRIENDLY AND HELPFUL. ALL THIS IS WHAT KEEPS ME COMING BACK. "
The price is CA $136
CA $158 total
includes taxes & fees
Jun 6 - Jun 7
Amsterdam Hotel
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.

Everything you need to know about Ossining vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ossining vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ossining vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Ossining vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ossining. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ossining vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ossining vacation rentals we have selected for you start as low as CA $123 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Ossining rentals

At Expedia, we put the best Ossining vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Ossining rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ossining vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ossining. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: You might want to consider this vacation home rental near Ossining, which is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. It offers a garden, a selection of games, and a spa tub so you can immerse yourself in your vacation.

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 Sing Sing Prison Museum and Ossining Historical Society, whereas Louis Engel Waterfront Park and Teatown Lake Reservation 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.

Recent reviews of Ossining properties
Expedia verified reviews

Tarrytown House Estate on the Hudson

Tarrytown House Estate on the Hudson

5/5 Excellent
"Lovely"
A verified traveller stayed at Tarrytown House Estate on the Hudson
Posted 17 hours ago
Tarrytown House Estate on the Hudson