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Ossining Vacation Rentals

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Vacation Rentals in Ossining

Exterior
Stamford Suites
2.5 star property
6.8 out of 10, (705)
"The hotel suite was larger than I expected. The staff was professional and friendly. The noise from the residential families was a minor nuisance. The halls, elevator, bathroom and common areas where dirty. No hot water or tea bags at breakfast."
The price is ￥22,523
per night
May 29 - May 30
Stamford Suites
Exterior
Waterfront Retreat Center for Health & Wellness
9.6 out of 10, Exceptional, (49)
"Beautiful location and old, well-maintained house. Really perfect for our family group of 17"
Waterfront Retreat Center for Health & Wellness
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 ￥28,746
per night
May 20 - May 21
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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Beach
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
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
Interior
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
10.0 out of 10, Exceptional, (3)
"Just as advertised! Met all our needs! I hope to be back"
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
Beach
Seascape Beach Home- Seas-the-Day at this cozy home on Shippan Point
The price is ￥54,523
per night
May 21 - May 22
Seascape Beach Home- Seas-the-Day at this cozy home on Shippan Point
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 ￥29,598
per night
May 15 - May 16
The Subterranean Haven
Terrace/patio
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (103)
"Pleasant stay"
Lower Lvl Private 2BR/1BA Family/Pet Friendly
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
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
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
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
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
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
Interior
Cozy Spacious Guest Suite 15 minutes from NYC
5.0 out of 10, (2)
"It was good "
The price is ￥14,020
per night
May 15 - May 16
Cozy Spacious Guest Suite 15 minutes from NYC
Interior
Mini Garden-Apartment near New York City
Mini Garden-Apartment near New York City
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (15)
"We so enjoyed our stay! The house was perfect for our family, conveniently located close to extended family and with the most beautiful view. The house had everything we needed and provided the perfect home base for spring break in our hometown. We even got to experience an earth quake ;) thank you!!"
Serenity Awaits at this Cozy Lakeside Bungalow
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 ￥77,734
per night
May 25 - May 26
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Fridge, microwave, oven, stovetop
Delightful Entire 2 Bedroom Apartment - 30 min train to NYC
10.0 out of 10, Exceptional, (1)
"AAA++ for place and host"
The price is ￥24,769
per night
May 15 - May 16
Delightful Entire 2 Bedroom Apartment - 30 min train to NYC
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.

Other types of properties in Ossining you may be interested in

Restaurant
Armoni Inn & Suites
3.5 star property
6.2 out of 10, (1103)
"Food"
The price is ￥9,509
per night
May 22 - May 23
Armoni Inn & Suites
Interior
Royal Regency Hotel
3.5 star property
8.0 out of 10, Very Good, (1457)
"Great stay! Will be coming back simply because it’s so close to the city and they have parking that is free for guests! "
The price is ￥35,152
per night
May 16 - May 17
Royal Regency Hotel
Desk, laptop workspace, blackout drapes, iron/ironing board
Baymont by Wyndham White Plains - Elmsford
2.5 star property
8.2 out of 10, Very Good, (1015)
"Always clean. Good breakfast, rates are good"
The price is ￥19,966
per night
May 27 - May 28
Baymont by Wyndham White Plains - Elmsford
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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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 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 8 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 Nelson Park and Louis Engel Waterfront Park 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

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

5/5 Excellent
"Always clean. Good breakfast, rates are good"
A verified traveler stayed at Baymont by Wyndham White Plains - Elmsford
Posted 10 hours ago
Baymont by Wyndham White Plains - Elmsford