Boardwalk over marshland on the trail at Teatown Lake Reservation in Ossining, New York.

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Our top choices for Ossining hotels

Windrose On Hudson

Windrose On Hudson
3.0 star property
Ossining
8.4 out of 10, Very Good, (164 reviews)
"Ev chargers on site. Lovely grounds and facilities. Will definitely stay here next time i am in the area."
United States
Andrew
The price is ¥32,978
¥36,727 total
includes taxes & fees
Jun 28 - Jun 29
Windrose On Hudson

Ossining Vacation Rental Near River, Trails & Mta!

Ossining Vacation Rental Near River, Trails & Mta!
3.0 star property
Ossining
The price is ¥48,963
¥141,190 total
includes taxes & fees
Jun 14 - Jun 15
Ossining Vacation Rental Near River, Trails & Mta!

Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is ¥176,299
¥274,231 total
includes taxes & fees
Jun 29 - Jun 30
Summer Pool Oasis Custom Bar Arcade Pool Table

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very Good, (54 reviews)
"Clean nice new hotel"
United States
Amjad
The price is ¥17,609
¥21,680 total
includes taxes & fees
Jun 14 - Jun 15
Comfort Suites Central Valley - Woodbury

Heidi's Inn

Heidi's Inn
2.5 star property
Brewster
8.8 out of 10, Excellent, (849 reviews)
"I had a lovely stay - highly recommend!"
United States
Catherine
The price is ¥23,624
¥25,603 total
includes taxes & fees
Jun 15 - Jun 16
Heidi's Inn

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1,025 reviews)
"Gorgeous setting, beautiful and comfortable room and easy access."
United States
Gwen
The price is ¥23,561
¥29,010 total
includes taxes & fees
Jun 15 - Jun 16
Overlook Lodge at Bear Mountain

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, (382 reviews)
"Great place to stay."
United States
Sai
The price is ¥21,472
¥24,693 total
includes taxes & fees
Jul 5 - Jul 6
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,120 reviews)
"Breakfast was ok parking and staff where excellent "
United States
Victor
The price is ¥21,966
¥27,044 total
includes taxes & fees
Jun 21 - Jun 22
Hampton Inn Harriman Woodbury

The Thayer Hotel at West Point

The Thayer Hotel at West Point
3.5 star property
West Point
9.0 out of 10, Wonderful, (735 reviews)
"It is an old hotel but well maintained, helpful staff and gorgeous views."
United States
Andrey
The price is ¥26,790
¥35,812 total
includes taxes & fees
Jul 1 - Jul 2
The Thayer Hotel at West Point

Cambria Hotel & Suites - White Plains Downtown

Cambria Hotel & Suites - White Plains Downtown
3.5 star property
White Plains
9.4 out of 10, Exceptional, (1,011 reviews)
"A great place to stay if you're in the area."
United States
Sean
The price is ¥32,292
¥36,934 total
includes taxes & fees
Jun 28 - Jun 29
Cambria Hotel & Suites - White Plains Downtown

West Point Motel

West Point Motel
2.5 star property
Highland Falls
8.6 out of 10, Excellent, (706 reviews)
"Stayed here numerous times friendly staff and very nice place close to post."
United States
Michael
The price is ¥19,201
¥23,641 total
includes taxes & fees
Jun 30 - Jul 1
West Point Motel

Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury
4.0 star property
Danbury
9.2 out of 10, Wonderful, (1,010 reviews)
"Great place to step in the area the restaurant in the lobby is awesome great food and ambiance"
United States
Laura
The price is ¥26,123
¥30,041 total
includes taxes & fees
Jul 6 - Jul 7
Hotel Zero Degrees Danbury

Hampton Inn Paramus

Hampton Inn Paramus
2.5 star property
Paramus
9.2 out of 10, Wonderful, (1,010 reviews)
"Excellent stay, rooms were clean, staff was helpful and friendly & breakfast was great."
United States
Carlos
The price is ¥23,320
¥26,731 total
includes taxes & fees
Jun 21 - Jun 22
Hampton Inn Paramus

Ethan Allen Hotel

Ethan Allen Hotel
3.5 star property
Danbury
8.0 out of 10, Very Good, (1,251 reviews)
"Hotel and visit were great, definitely recommend."
United States
Kathryn
The price is ¥17,091
¥19,655 total
includes taxes & fees
Jul 8 - Jul 9
Ethan Allen Hotel

Dream Hotel Bronx

Dream Hotel Bronx
2.0 star property
South Side
7.2 out of 10, Good, (96 reviews)
"No phone, no iron, bed was tiny even though it was listed as a King"
United States
Jenna
The price is ¥19,311
¥21,508 total
includes taxes & fees
Jul 2 - Jul 3
Dream Hotel Bronx

Tappan Zee Hotel

Tappan Zee Hotel
2.0 star property
West Nyack
6.4 out of 10, (669 reviews)
"Great stay…."
United States
Mariya
The price is ¥11,756
¥13,681 total
includes taxes & fees
Jun 14 - Jun 15
Tappan Zee Hotel

Holiday Inn Express West Point by IHG

Holiday Inn Express West Point by IHG
2.5 star property
Fort Montgomery
9.0 out of 10, Wonderful, (255 reviews)
"very nice place"
United States
Howard
The price is ¥24,322
¥28,732 total
includes taxes & fees
Jul 7 - Jul 8
Holiday Inn Express West Point by IHG

Red Carpet Inn

Red Carpet Inn
2.0 star property
Cove - East Side - Shippan
6.8 out of 10, (1,023 reviews)
"I enjoyed my stay amazing food places around and comfortable"
United States
Alonzo
The price is ¥13,382
¥15,390 total
includes taxes & fees
Jun 15 - Jun 16
Red Carpet Inn

Tarrytown House Estate

Tarrytown House Estate
3.5 star property
Tarrytown
8.2 out of 10, Very Good, (1,114 reviews)
"Great place to stay"
United States
Deanna
The price is ¥20,943
¥29,792 total
includes taxes & fees
Jun 30 - Jul 1
Tarrytown House Estate

Comfort Inn Brewster

Comfort Inn Brewster
2.5 star property
Brewster
8.8 out of 10, Excellent, (570 reviews)
"It was home away from home, very quiet and relaxing. Staff was phenomenal "
United States
Lorether
The price is ¥23,557
¥25,532 total
includes taxes & fees
Jul 5 - Jul 6
Comfort Inn Brewster
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Stay near popular Ossining attractions

Learn more about Ossining

Sing Sing Prison Museum offers a fascinating glimpse into America's most notorious correctional facility, with guided tours by former officers. Hike the scenic Old Croton Aqueduct Trail and then grab lunch at one of the diverse restaurants along the Hudson River waterfront.

Photo by louann ohora
Open Photo by louann ohora

Top Ossining Hotel Reviews

More cheap stays in Ossining

Frequently asked questions

Where is the best place to stay in Ossining?
Windrose On Hudson is one of the top choices for your stay based on our traveler data. This hotel offers free parking and a fitness center. Other good choices for your visit to the area are Baymont by Wyndham White Plains - Elmsford and Tarrytown House Estate. See all available top hotels, or vacation rentals in Ossining.
What are some of the best vacation rentals that Ossining has to offer?
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!: This Ossining vacation home rental is located near skiing and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. See all vacation rentals in Ossining.
If I need to cancel my hotel reservation in Ossining, will I receive a refund?
Yes! You'll find that most hotel room reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If your reservation is non-refundable, it might still be possible to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Ossining.
Where can I learn more about changing or cancelling my trip to Ossining?
For more information about rescheduling or cancelling your trip to Ossining, head over to our customer service page.
Where is the best place to stay with easy access to Ossining Historical Society?
La Quinta Inn & Suites by Wyndham White Plains - Elmsford is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and an indoor pool. You'll find it 6.8 mi (11 km) from Ossining Historical Society. Other good choices in the area include Comfort Inn & Suites and Crabtree's Kittle House Restaurant & Inn.
What about the best place to stay near Hudson Hills Golf Course?
One of the top choices for your stay is Crabtree's Kittle House Restaurant & Inn, located 4.1 mi (6.6 km) from Hudson Hills Golf Course, and this 3.5-star B&B offers free breakfast and a restaurant. Holiday Inn Mt. Kisco, an IHG Hotel, located 5.1 mi (8.2 km) away, is another good choice for your stay.
What are some accommodations with pools in Ossining?
Baymont by Wyndham White Plains - Elmsford: Hotel located near Westchester County Center. Offers daily, an indoor pool, and complimentary wired internet access. Tarrytown House Estate and Hyatt Regency Greenwich are a couple of other choices that feature an onsite pool. View all hotels with pools in Ossining.
What's the best place to stay near Westchester County Airport (HPN)?
Doral Arrowwood is one of the top choices for your stay and is a popular 4-star hotel featuring a golf course and 2 restaurants. It's located 2 mi (3.3 km) from Westchester County Airport. Other good choices near the airport include Crowne Plaza White Plains - Downtown and La Quinta Inn & Suites by Wyndham Armonk Westchester.
How is it to stay in Ossining?
Visitors can enjoy all that Ossining has to offer including the restaurants, parks, and golf courses. Tourists can also enjoy the city's university setting, monuments, and museums. A top sight in the area is Woodbury Common Premium Outlets. In Ossining, there are 35 hotels and other accommodations to choose from. Find out more about Ossining.
What is there to see in Ossining?
Cultural venues include Sing Sing Prison Museum and Ossining Historical Society. Landmarks like Sing Sing Correctional Facility, Thomas J. Watson Research Center, and Ossining Public Library might be worth a visit. Natural beauty is on display at Teatown Lake Reservation, Merchants Square, and Pleasant Square. Check out what more to see and do in Expedia's Ossining guide.
How can I get around Ossining?
To venture out into the surrounding area, hop on a train at Ossining Station. If you want to venture out around the area, you may want a rental car in Ossining for your journey.
What's the weather like in Ossining?
The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 34°F. Average annual precipitation for Ossining is 51 inches.

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