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Holiday Rentals in Ossining

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Holiday Rentals in Ossining

Exterior
Stamford Suites
2.5 star property
6.8 out of 10, (705)
"Big clean spacious rooms, easily walkable to Stamford downtown with free breakfast. Property is not in great condition but otherwise centrally located with free parking."
The price is €162
includes taxes & fees
29 May - 30 May
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 €252
includes taxes & fees
20 May - 21 May
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 cot
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 €582
includes taxes & fees
16 May - 17 May
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 €194
includes taxes & fees
16 May - 17 May
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
Smart TV, video games, DVD player, books
Bright & Spacious Exec or Relo Home with 5BR & 2FB: Ideal for Extended Stays
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!!!"
Bright & Spacious Exec or Relo Home with 5BR & 2FB: Ideal for Extended Stays
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 €157
includes taxes & fees
16 May - 17 May
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 €869
includes taxes & fees
19 May - 20 May
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 €277
includes taxes & fees
16 May - 17 May
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 €63
includes taxes & fees
22 May - 23 May
Armoni Inn & Suites
Interior
Royal Regency Hotel
3.5 star property
8.0 out of 10, Very good, (1462)
"Very beautiful place "
The price is €203
includes taxes & fees
21 May - 22 May
Royal Regency Hotel
Desk, laptop workspace, blackout curtains, iron/ironing board
Baymont by Wyndham White Plains - Elmsford
2.5 star property
8.2 out of 10, Very good, (1002)
"Always clean. Good breakfast, rates are good"
The price is €132
includes taxes & fees
27 May - 28 May
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.

Frequently asked questions

Can I find a holiday rental in Ossining?

Yes, there are holiday rentals close to the most popular sights in Ossining, or you can select a more secluded 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 are some of the best holiday rentals that Ossining has to offer?

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: This holiday home rental outside of Ossining is located on a lake, and has a fireplace, a patio and a BBQ 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 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Ossining?

With 8 Expedia holiday rentals, you're guaranteed 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 holiday rental in Ossining like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Ossining. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.