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Ossining Vacation Rentals

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Our top choices for Ossining vacation rentals

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
$224 nightly
The price is $250
Jan 14 - Jan 15
Total with taxes and fees
Windrose On Hudson

Vacation Home in Ossining

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
$773 nightly
The price is $861
Jan 21 - Jan 22
Total with taxes and fees
NEW 45 Wolden Rd Ossining NY 10562
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.
$869 nightly
The price is $893
Jan 21 - Jan 22
Total with taxes and fees
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
2.0 star property
$357 nightly
The price is $398
Jan 14 - Jan 15
Total with taxes and fees
Polished 1BR w/ Accessible Room Features + Sauna
2.0 star property
$361 nightly
The price is $402
Jan 14 - Jan 15
Total with taxes and fees
1BR Queen near NYC | Trails, Biking & Sauna Bliss

Aparthotel in Ossining

Near NYC! | Stylish Guestroom
2.0 star property
$381 nightly
The price is $424
Jan 14 - Jan 15
Total with taxes and fees
Near NYC! | Stylish Guestroom

LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built
3.0 star property
8.4 out of 10, Very Good, (260 reviews)
"Our stay was awesome, clean, cozy and we slept well."
United States
Hidelisa
$107 nightly
The price is $126
Jan 14 - Jan 15
Total with taxes and fees
LIV Hotel Bronx - Newly Built

Comfort Inn Brewster

Comfort Inn Brewster
2.5 star property
9.0 out of 10, Wonderful, (535 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
$127 nightly
The price is $137
Jan 18 - Jan 19
Total with taxes and fees
Comfort Inn Brewster

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
9.0 out of 10, Wonderful, (1,027 reviews)
"Good food hot tub great bed was wonderful area beautiful staff so nice"
United States
vontisha
$94 nightly
The price is $110
Feb 1 - Feb 2
Total with taxes and fees
DoubleTree by Hilton Hotel Nanuet

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
$98 nightly
The price is $120
Jan 25 - Jan 26
Total with taxes and fees
Hampton Inn Harriman Woodbury

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
$99 nightly
The price is $113
Feb 12 - Feb 13
Total with taxes and fees
Overlook Lodge at Bear Mountain

Ethan Allen Hotel

Ethan Allen Hotel
3.5 star property
7.8 out of 10, Good, (1,114 reviews)
"Clean room | Staff | Breakfast | Business-friendly"
United States
Eimy
$102 nightly
The price is $118
Feb 5 - Feb 6
Total with taxes and fees
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
9.2 out of 10, Wonderful, (309 reviews)
"We enjoyed our stay. "
United States
Anne
$122 nightly
The price is $140
Jan 25 - Jan 26
Total with taxes and fees
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

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
$125 nightly
The price is $136
Jan 14 - Jan 15
Total with taxes and fees
Heidi's Inn

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
$89 nightly
The price is $102
Jan 18 - Jan 19
Total with taxes and fees
Inn on the Hudson

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
$151 nightly
The price is $171
Jan 19 - Jan 20
Total with taxes and fees
The Thayer Hotel at West Point

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
$100 nightly
The price is $113
Jan 26 - Jan 27
Total with taxes and fees
West Point Motel

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
2.5 star property
8.2 out of 10, Very Good, (1,489 reviews)
"Enjoyed the free breakfast and the workout room had options; great location for access into city"
United States
Kathleen Elizabeth
$116 nightly
The price is $132
Feb 1 - Feb 2
Total with taxes and fees
Baymont by Wyndham White Plains - Elmsford

Tarrytown House Estate

Tarrytown House Estate
3.5 star property
8.2 out of 10, Very Good, (1,007 reviews)
"Hotel was beautiful and clean "
United States
April
$142 nightly
The price is $163
Jan 15 - Jan 16
Total with taxes and fees
Tarrytown House Estate

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
$81 nightly
The price is $90
Jan 18 - Jan 19
Total with taxes and fees
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 vacation rentals

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

Ossining vacation 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 low season months. For more hustle and bustle, you may prefer to visit Ossining in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ossining rentals

At Expedia, we put the best Ossining vacation 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 vacation.

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 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?

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

How many vacation rentals will I find in Ossining?

With 7 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 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 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.