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Ossining Holiday Rentals

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Our top choices for Ossining holiday rentals

Windrose On Hudson

Windrose On Hudson
3.0 star property
Ossining
8.2 out of 10, Very good, (107 reviews)
"Clean room, staff were very welcoming"
United States
Semaj
The price is AU$336
includes taxes & fees
26 Jan - 27 Jan
Windrose On Hudson

NEW 45 Wolden Rd Ossining NY 10562

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
Ossining
The price is AU$1,330
includes taxes & fees
21 Jan - 22 Jan
NEW 45 Wolden Rd Ossining NY 10562

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
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 AU$1,322
includes taxes & fees
21 Jan - 22 Jan
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Polished 1BR w/ Accessible Room Features + Sauna

Polished 1BR w/ Accessible Room Features + Sauna
2.0 star property
Ossining
The price is AU$585
includes taxes & fees
13 Jan - 14 Jan
Polished 1BR w/ Accessible Room Features + Sauna

1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
2.0 star property
Ossining
The price is AU$585
includes taxes & fees
13 Jan - 14 Jan
1BR Queen near NYC | Trails, Biking & Sauna Bliss

Near NYC! | Stylish Guestroom

Near NYC! | Stylish Guestroom
2.0 star property
Ossining
The price is AU$625
includes taxes & fees
14 Jan - 15 Jan
Near NYC! | Stylish Guestroom

LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built
3.0 star property
Bronx
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 AU$189
includes taxes & fees
13 Jan - 14 Jan
LIV Hotel Bronx - Newly Built

Comfort Inn Brewster

Comfort Inn Brewster
2.5 star property
Brewster
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 AU$205
includes taxes & fees
15 Jan - 16 Jan
Comfort Inn Brewster

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
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 AU$161
includes taxes & fees
1 Feb - 2 Feb
DoubleTree by Hilton Hotel Nanuet

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,035 reviews)
"Easy check in, clean room, very good breakfast."
United States
Robert
The price is AU$180
includes taxes & fees
25 Jan - 26 Jan
Hampton Inn Harriman Woodbury

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
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 AU$167
includes taxes & fees
19 Jan - 20 Jan
Overlook Lodge at Bear Mountain

Ethan Allen Hotel

Ethan Allen Hotel
3.5 star property
Danbury
7.8 out of 10, Good, (1,113 reviews)
"Clean room | Staff | Breakfast | Business-friendly"
United States
Eimy
Ethan Allen Hotel

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

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG
2.5 star property
Danbury
9.2 out of 10, Wonderful, (309 reviews)
"We enjoyed our stay. "
United States
Anne
The price is AU$210
includes taxes & fees
18 Jan - 19 Jan
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Heidi's Inn

Heidi's Inn
2.5 star property
Brewster
8.8 out of 10, Excellent, (815 reviews)
"A fine motel, great staff & very flexible"
United States
Andy
The price is AU$203
includes taxes & fees
14 Jan - 15 Jan
Heidi's Inn

Inn on the Hudson

Inn on the Hudson
2.0 star property
Peekskill
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 AU$152
includes taxes & fees
18 Jan - 19 Jan
Inn on the Hudson

The Thayer Hotel at West Point

The Thayer Hotel at West Point
3.5 star property
West Point
9.0 out of 10, Wonderful, (681 reviews)
"Location was great & staying at a historic hotel was delightful."
United States
Bobby
The price is AU$251
includes taxes & fees
18 Jan - 19 Jan
The Thayer Hotel at West Point

West Point Motel

West Point Motel
2.5 star property
Highland Falls
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 AU$169
includes taxes & fees
25 Jan - 26 Jan
West Point Motel

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
2.5 star property
Elmsford
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 AU$186
includes taxes & fees
15 Jan - 16 Jan
Baymont by Wyndham White Plains - Elmsford

Tarrytown House Estate

Tarrytown House Estate
3.5 star property
Tarrytown
8.2 out of 10, Very good, (1,006 reviews)
"Hotel was beautiful and clean "
United States
April
The price is AU$243
includes taxes & fees
15 Jan - 16 Jan
Tarrytown House Estate

Hampton Inn Nanuet

Hampton Inn Nanuet
2.5 star property
Nanuet
7.8 out of 10, Good, (1,004 reviews)
"Great hotel, nice and clean "
United States
Andrea
The price is AU$135
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

Find out more about Ossining

Everything you need to know about Ossining holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ossining holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Ossining holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ossining holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ossining holiday rentals we have selected for you start as low as AU$224 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Ossining rentals

At Expedia, we put the best Ossining holiday 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 holiday.

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 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.