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Ossining Holiday Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Ossining holiday rentals

Restaurant
Windrose On Hudson

Windrose On Hudson

Windrose On Hudson
3.0 star property
8.2 out of 10, Very good, (107 reviews)
"Clean room, staff were very welcoming"
United States
Semaj
The price is HK$1,572
HK$1,751 total
includes taxes & fees
25 Jan - 26 Jan
Windrose On Hudson
5 bedrooms
NEW 45 Wolden Rd Ossining NY 10562

Holiday Home in Ossining

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
The price is HK$2,522
HK$6,666 total
includes taxes & fees
13 Jan - 14 Jan
NEW 45 Wolden Rd Ossining NY 10562
Outdoor banquet area
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Holiday Home in Ossining

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
9.2 out of 10, Wonderful, (7 reviews)
"Communication was excellent. The house itself is older and fine for its age, but "
United States
Jonathan O.
The price is HK$3,289
HK$6,941 total
includes taxes & fees
21 Jan - 22 Jan
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Interior
Polished 1BR w/ Accessible Room Features + Sauna

Aparthotel in Ossining

Polished 1BR w/ Accessible Room Features + Sauna
2.0 star property
The price is HK$2,426
HK$3,075 total
includes taxes & fees
14 Jan - 15 Jan
Polished 1BR w/ Accessible Room Features + Sauna
Interior
1BR Queen near NYC | Trails, Biking & Sauna Bliss

Aparthotel in Ossining

1BR Queen near NYC | Trails, Biking & Sauna Bliss
2.0 star property
The price is HK$2,426
HK$3,118 total
includes taxes & fees
14 Jan - 15 Jan
1BR Queen near NYC | Trails, Biking & Sauna Bliss
Interior
Near NYC! | Stylish Guestroom

Aparthotel in Ossining

Near NYC! | Stylish Guestroom
2.0 star property
The price is HK$2,621
HK$3,289 total
includes taxes & fees
14 Jan - 15 Jan
Near NYC! | Stylish Guestroom
Lobby
LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built
3.0 star property
8.4 out of 10, Very good, (259 reviews)
"Our stay was awesome, clean, cozy and we slept well."
United States
Hidelisa
The price is HK$835
HK$985 total
includes taxes & fees
13 Jan - 14 Jan
LIV Hotel Bronx - Newly Built
Lobby
Comfort Inn Brewster

Comfort Inn Brewster

Comfort Inn Brewster
2.5 star property
9.0 out of 10, Wonderful, (533 reviews)
"Always great service and clean, comfy rooms. Breakfast is also decent every time, which isn’t always the case at hotels "
United States
Jared
The price is HK$987
HK$1,070 total
includes taxes & fees
15 Jan - 16 Jan
Comfort Inn Brewster
Indoor pool, open 8:30 AM to 9:30 PM, pool loungers
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
9.0 out of 10, Wonderful, (1,026 reviews)
"Good food hot tub great bed was wonderful area beautiful staff so nice"
United States
vontisha
The price is HK$722
HK$841 total
includes taxes & fees
1 Feb - 2 Feb
DoubleTree by Hilton Hotel Nanuet
Lobby
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
9.2 out of 10, Wonderful, (1,035 reviews)
"Easy check in, clean room, very good breakfast."
United States
Robert
The price is HK$761
HK$936 total
includes taxes & fees
25 Jan - 26 Jan
Hampton Inn Harriman Woodbury
Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
8.4 out of 10, Very good, (1,004 reviews)
"The stone lodges are cute and cozy and the staff were quick and helpful if you needed anything. Great for a short stay at a reasonable price."
United States
Judith
The price is HK$770
HK$872 total
includes taxes & fees
13 Jan - 14 Jan
Overlook Lodge at Bear Mountain
Dinner served
Ethan Allen Hotel

Ethan Allen Hotel

Ethan Allen Hotel
3.5 star property
7.8 out of 10, Good, (1,113 reviews)
"Clean room | Staff | Breakfast | Business-friendly"
United States
Eimy
Ethan Allen Hotel
Exterior
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG
2.5 star property
9.2 out of 10, Wonderful, (309 reviews)
"We enjoyed our stay. "
United States
Anne
The price is HK$951
HK$1,094 total
includes taxes & fees
18 Jan - 19 Jan
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG
Lobby sitting area
Heidi's Inn

Heidi's Inn

Heidi's Inn
2.5 star property
8.8 out of 10, Excellent, (815 reviews)
"A fine motel, great staff & very flexible"
United States
Andy
The price is HK$977
HK$1,059 total
includes taxes & fees
14 Jan - 15 Jan
Heidi's Inn
View from property
Inn on the Hudson

Inn on the Hudson

Inn on the Hudson
2.0 star property
7.0 out of 10, Good, (1,000 reviews)
"They were wonderful. As much as the lay out may seem weird and inconveniencing I found it to be quite quaint. "
United States
NATASHA
The price is HK$694
HK$793 total
includes taxes & fees
18 Jan - 19 Jan
Inn on the Hudson
Lobby sitting area
The Thayer Hotel at West Point

The Thayer Hotel at West Point

The Thayer Hotel at West Point
3.5 star property
9.0 out of 10, Wonderful, (681 reviews)
"Location was great & staying at a historic hotel was delightful."
United States
Bobby
The price is HK$968
HK$1,298 total
includes taxes & fees
18 Jan - 19 Jan
The Thayer Hotel at West Point
Aerial view
West Point Motel

Motel in Highland Falls

West Point Motel
2.5 star property
8.6 out of 10, Excellent, (665 reviews)
"The convenience of a key box for late arrivals was very helpful. Room was clean and location to restaurants was very good. Enjoyed stay at this hotel very much. Will definitely be back!"
United States
June
The price is HK$779
HK$882 total
includes taxes & fees
25 Jan - 26 Jan
West Point Motel
Free daily self-service breakfast
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
2.5 star property
8.2 out of 10, Very good, (1,488 reviews)
"Enjoyed the free breakfast and the workout room had options; great location for access into city"
United States
Kathleen Elizabeth
The price is HK$848
HK$970 total
includes taxes & fees
15 Jan - 16 Jan
Baymont by Wyndham White Plains - Elmsford
Exterior
Tarrytown House Estate

Tarrytown House Estate

Tarrytown House Estate
3.5 star property
8.2 out of 10, Very good, (1,006 reviews)
"Hotel was beautiful and clean "
United States
April
The price is HK$938
HK$1,268 total
includes taxes & fees
15 Jan - 16 Jan
Tarrytown House Estate
Premium bedding, pillow-top beds, in-room safe, desk
Hampton Inn Nanuet

Hampton Inn Nanuet

Hampton Inn Nanuet
2.5 star property
7.8 out of 10, Good, (1,004 reviews)
"Great hotel, nice and clean "
United States
Andrea
The price is HK$633
HK$705 total
includes taxes & fees
18 Jan - 19 Jan
Hampton Inn Nanuet
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

Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

10/10 Excellent
"The room was large, clean and very comfortable. The staff we always pleasant and welcoming. The breakfasts had good variety. I really enjoyed my stay."
Sue 5-night trip
Posted 1 day ago
Hampton Inn & Suites Yonkers

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:

  • View our selection of featured holiday rentals in Ossining
  • Use the map to find apartments and other holiday homes in the Ossining neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Ossining while they last

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

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?

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

How many holiday rentals will I find in Ossining?

With 7 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 Teatown Lake Reservation and Merchants Square 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.