Photo by regina palmieri

Search Ossining hotels

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
2 Jan - 3 Jan
Tomorrow
3 Jan - 4 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Ossining hotels

House
Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
Ossining
The price is NZ$1,502
includes taxes & fees
5 Jan - 6 Jan
Foliage at Westchester Manor - Near Sleepy Hollow
Terrace/patio
Windrose On Hudson

Windrose On Hudson

Windrose On Hudson
3.0 star property
Ossining
8.2 out of 10, Very good, (106)
"Clean room, staff were very welcoming"
United States
Semaj
The price is NZ$381
includes taxes & fees
4 Jan - 5 Jan
Windrose On Hudson
Free daily self-service breakfast
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG

Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG

Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
2.5 star property
Peekskill
9.2 out of 10, Wonderful, (1005)
"Very comfortable beds,clean and breakfast was great."
United States
Dawn
The price is NZ$252
includes taxes & fees
5 Jan - 6 Jan
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
Exterior
The Abbey Inn & Spa

The Abbey Inn & Spa

The Abbey Inn & Spa
4.0 star property
Peekskill
9.2 out of 10, Wonderful, (233)
"Friendly staff and a great place to get away and recharge!"
United States
Ariana
The price is NZ$635
includes taxes & fees
6 Jan - 7 Jan
The Abbey Inn & Spa
Porch
Cold Spring Hotel

Cold Spring Hotel

Cold Spring Hotel
3.0 star property
Cold Spring
8.6 out of 10, Excellent, (155)
"The owner is so warm and kind. The room was clean. Great place to stay for the weekend! "
United States
Wydayessi
Cold Spring Hotel
Terrace/patio
J House Greenwich

J House Greenwich

J House Greenwich
4.0 star property
Riverside
9.0 out of 10, Wonderful, (1003)
"Nice hotel"
United States
Aleksandr
J House Greenwich
Standard Room, 2 Queen Beds, Accessible (ADA)
West Point Motel

West Point Motel

West Point Motel
2.5 star property
Highland Falls
8.6 out of 10, Excellent, (663)
"Clean room and so close to West Point!! Great experience 👍 "
United States
SHANNON
The price is NZ$196
includes taxes & fees
3 Feb - 4 Feb
West Point Motel
Bar (on property)
The Thayer Hotel at West Point

The Thayer Hotel at West Point

The Thayer Hotel at West Point
3.5 star property
West Point
9.0 out of 10, Wonderful, (675)
"Location was great & staying at a historic hotel was delightful."
United States
Bobby
The price is NZ$366
includes taxes & fees
5 Jan - 6 Jan
The Thayer Hotel at West Point
Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1008)
"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 NZ$203
includes taxes & fees
28 Jan - 29 Jan
Overlook Lodge at Bear Mountain
Front of property
Delamar Greenwich Harbor

Delamar Greenwich Harbor

Delamar Greenwich Harbor
4.0 star property
Greenwich
9.4 out of 10, Exceptional, (959)
"Great stay!!"
United States
Dana
The price is NZ$815
includes taxes & fees
4 Jan - 5 Jan
Delamar Greenwich Harbor
Lobby
Comfort Inn Brewster

Comfort Inn Brewster

Comfort Inn Brewster
2.5 star property
Brewster
9.0 out of 10, Wonderful, (529)
"Clean room. Great staff."
United States
Denise
The price is NZ$238
includes taxes & fees
1 Feb - 2 Feb
Comfort Inn Brewster
Lobby
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1023)
"Easy check in, clean room, very good breakfast."
United States
Robert
The price is NZ$209
includes taxes & fees
11 Jan - 12 Jan
Hampton Inn Harriman Woodbury
Free daily full breakfast
Holiday Inn Express West Point by IHG

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, (220)
"Breakfast was great!"
United States
Todd
The price is NZ$220
includes taxes & fees
11 Jan - 12 Jan
Holiday Inn Express West Point by IHG
Front of property
Heidi's Inn

Heidi's Inn

Heidi's Inn
2.5 star property
Brewster
8.8 out of 10, Excellent, (811)
"The staff was nice and the room was clean."
United States
Mike
The price is NZ$236
includes taxes & fees
4 Jan - 5 Jan
Heidi's Inn
View from property
Inn on the Hudson

Inn on the Hudson

Inn on the Hudson
2.0 star property
Peekskill
7.0 out of 10, Good, (1004)
"The location was very convenient. There is not a lot available in Peekskill and this place was very close to where we were going. The room was well cleaned and cared for the only drawback was that the heating unit was very, very noisy."
United States
Shelley
The price is NZ$177
includes taxes & fees
4 Jan - 5 Jan
Inn on the Hudson
Deluxe Room, 1 King Bed, Non Smoking
LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built
3.0 star property
Bronx
8.4 out of 10, Very good, (239)
"Nice place "
United States
Eric
The price is NZ$220
includes taxes & fees
4 Jan - 5 Jan
LIV Hotel Bronx - Newly Built
Indoor pool, seasonal outdoor pool
Marriott Park Ridge

Marriott Park Ridge

Marriott Park Ridge
3.5 star property
Park Ridge
8.8 out of 10, Excellent, (880)
"Great hotel"
United States
Christopher
The price is NZ$285
includes taxes & fees
4 Jan - 5 Jan
Marriott Park Ridge
Reception
Courtyard by Marriott Montvale

Courtyard by Marriott Montvale

Courtyard by Marriott Montvale
3.0 star property
Montvale
8.6 out of 10, Excellent, (658)
"Clean, comfortable space. Friendly staff. "
United States
AMANDA
The price is NZ$267
includes taxes & fees
15 Jan - 16 Jan
Courtyard by Marriott Montvale
Premium Double Room | In-room dining
FairBridge Inn & Suites at West Point

FairBridge Inn & Suites at West Point

FairBridge Inn & Suites at West Point
2.0 star property
Highland Falls
6.2 out of 10, (797)
"Excellent staff, super neat and clean room, very quiet and pleasant stay."
United States
Katherine
The price is NZ$196
includes taxes & fees
23 Jan - 24 Jan
FairBridge Inn & Suites at West Point
Exterior
The Lloyd Stamford, Tapestry Collection by Hilton

The Lloyd Stamford, Tapestry Collection by Hilton

The Lloyd Stamford, Tapestry Collection by Hilton
3.5 star property
Downtown Stamford
8.8 out of 10, Excellent, (440)
"Everything was just excellent. Perfect for our short stay and the staff was so kind. We are definitely returning here! "
United States
Meaghan
The price is NZ$329
includes taxes & fees
18 Jan - 19 Jan
The Lloyd Stamford, Tapestry Collection by Hilton
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Ossining attractions

Rest stop area beside interstate highway where travelers rest and sight see Tioga Reservoir and Dam in Pennsylvania New York state border

Travelers Rest

After visiting Travelers Rest, make a plan to see the other sights and activities in Ossining. Amble around the area's parks or visit its monuments.
See properties
Lovely spot in Westchester, NY
Photo by louann ohora
Open Photo by louann ohora

Teatown Lake Reservation

Explore the great outdoors at Teatown Lake Reservation, a lovely green space in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.
See properties

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.

See all hotels in Ossining
Main building at Maryknoll
Photo by louann ohora
Open Photo by louann ohora

Top Ossining Hotel Reviews

West Gate Inn Nyack

West Gate Inn Nyack

10/10 Excellent
"Staff and management professional hard work and all amenities included. "
Eric 1-night trip
Posted 22 hours ago
West Gate Inn Nyack

More cheap accommodation in Ossining

Comfort Inn Paramus - Hackensack

Comfort Inn Paramus - Hackensack

50 N Rte 17 Paramus NJ
The price is NZ$205 per night from 25 Jan to 26 Jan
NZ$205
25 Jan - 26 Jan
includes taxes & fees
8.8/10 Excellent! (1,011 reviews)

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 traveller data. This hotel offers free parking and a fitness centre. Other good options for your visit to the area are Ramada by Wyndham Bronx and Royal Regency Hotel. See all available top hotels, or vacation rentals in Ossining.
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 of 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. See all vacation rentals in Ossining.
If I need to cancel my hotel reservation in Ossining, will I receive a refund?
Yes, most hotel bookings are fully refundable if you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If your reservation is non-refundable, you may still be able to cancel and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Ossining.
What are some accommodation options with pools in Ossining?
DoubleTree by Hilton Hotel Nanuet: Features a snack bar/deli, a pool and free self parking. Hotel NoMa, Trademark Collection by Wyndham and Sonesta White Plains Downtown are a couple of other choices with an on-site pool. View all hotels with pools in Ossining.
What's it like 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. In Ossining, there are 22 hotels and other accommodation options to choose from. Find out more about Ossining.
What should I do while I'm visiting 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. Take a look at what more there is to see and do in Expedia's Ossining guide.
What's the best way to get around Ossining?
To venture out into the surrounding area, take a train from 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 temperature of 22°C, while the coldest months are January and February, with an average of 1°C. Average annual precipitation for Ossining is 1302 mm.

Explore a world of travel with Expedia