Photo by Linda Zanetti

Holiday Rentals in Ossining

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Holiday Rentals in Ossining

Stamford Suites

3.0 star property
6.8 out of 10, (773)
"It was in walking distance of the event we were going to."
The price is €222
includes taxes & fees
20 Jan - 21 Jan
Stamford Suites

Waterfront Retreat Center for Health & Wellness

9.6 out of 10, Exceptional, (56)
"Very comfortable stay with lots of room to spread out. Interesting older house with many unique features. We were happy to learn that they recently installed a new furnace and a dishwasher. Lots of cookware and dishes. We spread out over two dining rooms for mealtime which worked well for us. "
Waterfront Retreat Center for Health & Wellness

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (106)
"Great place and host!"
The price is €246
includes taxes & fees
15 Jan - 16 Jan
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Global Luxury Suites White Plains

3.5 star property
6.8 out of 10, (27)
"Great location, friendly people, great apartment "
Global Luxury Suites White Plains

The Subterranean Haven

9.0 out of 10, Wonderful, (6)
"Great communication, house was perfect in size and location"
The price is €192
includes taxes & fees
27 Jan - 28 Jan
The Subterranean Haven

Welcome to Villa Seabird, Luxury Escape on Long Island Sound

10.0 out of 10, Exceptional, (9)
"This was amazing Thanksgiving with my family. The house is amazing Jon was amazing host and his recommendation for food made you feel like million dollars. Can not thank you enough to share your beautiful home with us and see you in the summer."
Welcome to Villa Seabird, Luxury Escape on Long Island Sound

Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions

9.6 out of 10, Exceptional, (49)
"We stayed here with our 3 dogs between Christmas and New Years. It is in a gorgeous neighborhood of sprawling estate homes. This property had tons of room to spread out. The yard is HIGE and completely fenced in. The rooms are decorated with the photography work of the owner and other interesting pieces. Plenty to do on site and not too far from the city. Lisa was great and even let our dogs out to potty so we could relax traveling into the city for a show and dinner. We would love to...
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions

Lower Lvl Private 2BR/1BA Family/Pet Friendly

10.0 out of 10, Exceptional, (116)
"We had a great time staying in this property. It offers more amenities than if staying in a hotel, and at a reduced cost. Communication with owner was excellent, would highly recommend, and would definitely stay again."
Lower Lvl Private 2BR/1BA Family/Pet Friendly

Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor

7.8 out of 10, Good, (7)
"Unit was exactly as listed, very cozy! 10/10 would recommend! Unit was lovely, and the host was amazing! Would definitely book again!"
Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor

Stylish 3-bedroom 3rd fl Apt in Mount Vernon, NY

8.8 out of 10, Excellent, (13)
"The apartment was exactly as stated and shown in the photos"
Stylish 3-bedroom 3rd fl Apt in Mount Vernon, NY

Cozy Apartment-Just minutes from New York City

9.4 out of 10, Exceptional, (3)
"My stay was uneventful. Nice property in a gorgeous neighborhood. The apartment is in the basement with quite a few stairs to go up and down but is cute and clean. There is a full kitch but you have to bring your own pans. No tv's in the bedroom which was ok with me because after being gone all day , all i wanted to do was go to sleep. I would recommend and stay again."
Cozy Apartment-Just minutes from New York City

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

10.0 out of 10, Exceptional, (13)
"Beautiful modern home with great views over the pond and woods. Super comfortable and many amenities. I really appreciated how well stocked the kitchen was with pots and pans that you can actually cook with compared to most VRBO's. Only drawback is that the area isn't really walkable. Busy road with minimal shoulder and you can't get down to the pond. We drove to a number of great hikes in the area though. Bonus: the woods behind the house were home to a couple great horned owls calling to...
The price is €859
includes taxes & fees
15 Jan - 16 Jan
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Cozy private room

2.0 star property
7.0 out of 10, Good, (8)
"Property locked upon arrival. No communication of any kind re checking in, no email, no return of multiple phone calls at all. I needed to find another hotel and seek a full refund, which was given by Expedia. Terrible travel experience, beware."
Cozy private room

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (75)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Spacious & Cozy 1st Floor & Basement Apartment 15 min from NYC!

6.4 out of 10, (13)
"The host was SUPER friendly. Very helpful and informative. The ONLY thing i didn’t like about it, was it was a TAD bit smaller than what it looked like in the pics. But other than that, i have zero complaints or remarks whatsoever. The only thing i would have liked to know before my stay was that it’s in the basement of a house. I was under the assumption that it was in an actual apartment building. But i honestly cannot complain at all because the host was just THAT accommodating. Just the...
The price is €184
includes taxes & fees
15 Jan - 16 Jan
Spacious & Cozy 1st Floor & Basement Apartment 15 min from NYC!

The Safe House - High Tech Apt #2 - 3 Beds

9.6 out of 10, Exceptional, (35)
"Enjoyed my second stay at the Safe House. Plenty of space, great proximity to Greenwich downtown."
The price is €204
includes taxes & fees
15 Jan - 16 Jan
The Safe House - High Tech Apt #2 - 3 Beds

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (21)
"Great place all is as described and easy check in check out and host was very responsive."
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Yonkers Apt w/ Balcony: Walk to Train Station!

8.6 out of 10, Excellent, (27)
"Location was great! Clean apt. Spacious. The futon is not comfortable but it’s a futon it did not bother me. Good price!"
Yonkers Apt w/ Balcony: Walk to Train Station!

Cheerful Home in Yonkers NY

7.6 out of 10, Good, (4)
"To summarize without too many details we had to be placed in a hotel. I am sure once this house is given proper detailed updating it will be worth it. Please be clear you will Uber a lot unless you have a car or someone to pick you up from Yonkers."
Cheerful Home in Yonkers NY

Spectacular 2- bedroom Apt in Yonkers, NY

8.2 out of 10, Very good, (11)
"Nice place I would definitely stay again when in town for business. "
Spectacular 2- bedroom Apt in Yonkers, NY
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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Other types of properties in Ossining you may be interested in

Armoni Inn & Suites

3.5 star property
6.2 out of 10, (1791)
"Night reception was friendly"
The price is €58
includes taxes & fees
1 Feb - 2 Feb
Armoni Inn & Suites

Royal Regency Hotel

3.5 star property
8.2 out of 10, Very good, (1912)
"Very nice place. Friendly staff great breakfast."
The price is €116
includes taxes & fees
9 Feb - 10 Feb
Royal Regency Hotel

Hampton Inn White Plains/Tarrytown

3.0 star property
8.0 out of 10, Very good, (1006)
"Very friendly and helpful staff. Breakfast was good, better than most hotels I stay in. "
The price is €184
includes taxes & fees
25 Jan - 26 Jan
Hampton Inn White Plains/Tarrytown
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?

Lower Lvl Private 2BR/1BA Family/Pet Friendly: This holiday home rental outside of Ossining offers a patio, a terrace and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals will I find in Ossining?

With 6 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 Snowden Avenue Park and Nelson Park are a couple of picturesque spots to enjoy the outdoors. Sing Sing Correctional Facility and Teatown Lake Reservation 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.