Photo by regina palmieri

Find hotels in Ossining, NY from ₩126,696

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
Dec 15 - Dec 16
Tomorrow
Dec 16 - Dec 17
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Ossining hotels

Restaurant
Windrose On Hudson

Windrose On Hudson

Windrose On Hudson
3.0 star property
Ossining
8.2 out of 10, Very Good, (100)
Experience relaxation at this riverside retreat with a fitness center and vibrant bar/lounge. Near Van Cortlandt Manor and Croton Point Park, enjoy complimentary WiFi and parking while savoring breakfast at the cozy café.
"Clean room, staff were very welcoming"
United States
Semaj
The price is ₩247,567
₩275,729 total
includes taxes & fees
Dec 16 - Dec 17
Windrose On Hudson
House | 5 bedrooms
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 ₩609,871
₩1,376,687 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Foliage at Westchester Manor - Near Sleepy Hollow
Room, 2 Queen Beds, Accessible (Mobility/Hearing Impaired Accessible) | Premium bedding, desk, blackout drapes, iron/ironing board
La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City
3.0 star property
Waterside
6.6 out of 10, (1023)
Just off the interstate in Stamford, this hotel makes travel easy with free parking and breakfast. Swim year-round in the indoor pool, enjoy meals at City Limits restaurant, and appreciate the clean rooms and attentive service that guests consistently praise.
"The location is great and convenient! The staff is very kind and attentive!"
United States
Cruz
The price is ₩137,332
₩157,932 total
includes taxes & fees
Jan 4 - Jan 5, 2026
La Quinta Inn & Suites by Wyndham Stamford / New York City
Desk, free WiFi, bed sheets
Mamaroneck Motel

Mamaroneck Motel

Mamaroneck Motel
2.0 star property
Mamaroneck
6.6 out of 10, (503)
This Mamaroneck motel offers complimentary WiFi and self parking just minutes from Harbor Island Park and Emelin Theatre. Enjoy 24-hour front desk service while staying within a short drive of New Rochelle Station and Westchester County Airport.
"Convenient room at a good price."
United States
Jennifer
The price is ₩139,540
₩159,593 total
includes taxes & fees
Dec 16 - Dec 17
Mamaroneck Motel
Restaurant
Red Carpet Inn

Red Carpet Inn

Red Carpet Inn
2.0 star property
Cove - East Side - Shippan
6.4 out of 10, (1006)
Located near the train station, this hotel offers easy access to Chelsea Piers and Cove Island Park. Enjoy a meal at the restaurant or unwind with a drink at the bar while taking advantage of the free WiFi and parking.
"Great"
United States
Venie
The price is ₩125,221
₩144,003 total
includes taxes & fees
Dec 16 - Dec 17
Red Carpet Inn
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, (1001)
Historic lodge near Bear Mountain State Park offers deep-tissue massages and body wraps at the onsite spa. Enjoy drinks at the bar, meals at the café, and rooms with refrigerators and microwaves. Free WiFi and parking add convenience for exploring nearby attractions.
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
The price is ₩175,847
₩198,929 total
includes taxes & fees
Dec 16 - Dec 17
Overlook Lodge at Bear Mountain
Lobby
Amsterdam Hotel

Amsterdam Hotel

Amsterdam Hotel
2.0 star property
Downtown Stamford
8.4 out of 10, Very Good, (1726)
In this serene Stamford retreat near the train station, enjoy complimentary continental breakfast, WiFi, and parking. The fitness center energizes while the garden and terrace provide peaceful relaxation. Steps from shopping and restaurants with helpful staff to enhance your stay.
"Front desk staff very friendly and helpful."
United States
Vivian
Amsterdam Hotel
Standard Room, 1 King Bed | Premium bedding, desk, iron/ironing board, free WiFi
Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester
2.0 star property
Ardsley
8.6 out of 10, Excellent, (1007)
Discover nature just steps away with hiking trails accessible from the hotel's parking lot. After outdoor adventures, return to quiet rooms and helpful staff. Near Legoland Discovery Center and offering free breakfast, WiFi and parking.
"The rooms are clean, it's quiet, the staff is always nice "
United States
Angela
Ardsley Acres Hotel Westchester
Restaurant
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, (430)
Located close to the train station, this boutique hotel offers a 24-hour fitness center and restaurant with bar. Clean rooms provide a comfortable base for exploring Museum of Black World War II History and Stamford Center for the Arts.
"Beautiful hotel and lovely staff"
United States
Theodóra
The price is ₩229,015
₩263,367 total
includes taxes & fees
Dec 21 - Dec 22
The Lloyd Stamford, Tapestry Collection by Hilton
2 restaurants, American cuisine
Courtyard by Marriott Stamford Downtown

Courtyard by Marriott Stamford Downtown

Courtyard by Marriott Stamford Downtown
3.0 star property
Downtown Stamford
9.0 out of 10, Wonderful, (837)
Situated near Stamford Transportation Center, this hotel offers an indoor pool, hot tub, and 2 restaurants for post-exploration dining. Visit nearby Stamford Center for the Arts or enjoy a workout in the 24-hour fitness center.
"Great spot"
United States
Anthony
The price is ₩317,708
₩365,364 total
includes taxes & fees
Dec 21 - Dec 22
Courtyard by Marriott Stamford Downtown
Room, Multiple Beds, Non Smoking | Desk, iron/ironing board, rollaway beds, free WiFi
Super 8 by Wyndham Mahwah

Super 8 by Wyndham Mahwah

Super 8 by Wyndham Mahwah
2.5 star property
Mahwah
7.4 out of 10, Good, (1001)
This quiet Mahwah hotel offers free parking and WiFi, with a train station just a 16-minute walk away. Comfortable rooms provide a peaceful retreat, with helpful staff ready to assist at any hour.
"Room was clean and staff was helpful "
United States
Berldwin
The price is ₩110,532
₩126,696 total
includes taxes & fees
Dec 21 - Dec 22
Super 8 by Wyndham Mahwah
Terrace/patio
Courtyard by Marriott Mahwah

Courtyard by Marriott Mahwah

Courtyard by Marriott Mahwah
3.0 star property
Mahwah
8.2 out of 10, Very Good, (1000)
Surrounded by outdoor adventures like hiking trails and skiing, this quiet hotel offers clean, comfortable rooms and free WiFi. The convenient location places you near Suffern Railroad Museum and cafes with helpful service.
"Awesome rooms, super clean and the front desk staff was the best!! Coming back to the area in a few weeks and I would stay there again."
United States
Alfonso
The price is ₩158,115
₩181,239 total
includes taxes & fees
Dec 21 - Dec 22
Courtyard by Marriott Mahwah
Lobby
The Stamford Hotel

The Stamford Hotel

The Stamford Hotel
3.5 star property
Downtown Stamford
7.8 out of 10, Good, (1113)
Located by the Stamford Transportation Center, this hotel offers American cuisine at 700 Main restaurant, a fitness center, and bar. Walking distance to downtown dining and Stamford Town Center, with clean rooms that travelers consistently praise.
"Older rooms and hotel Great bartender and it was close to our event so it worked "
United States
James
The price is ₩144,817
₩166,539 total
includes taxes & fees
Dec 23 - Dec 24
The Stamford Hotel
Daily cooked-to-order breakfast for a fee
DoubleTree by Hilton Mahwah

DoubleTree by Hilton Mahwah

DoubleTree by Hilton Mahwah
4.0 star property
Mahwah
7.8 out of 10, Good, (934)
Peaceful accommodations at this hotel provide a tranquil base near Mahwah Station. The fitness center helps maintain your routine while the restaurant and bar offer convenient dining options. Free WiFi and parking enhance your stay near Suffern Railroad Museum.
"Easy check in."
United States
Nancy
The price is ₩168,429
₩193,061 total
includes taxes & fees
Dec 21 - Dec 22
DoubleTree by Hilton Mahwah
Bar (on property)
Hampton Inn & Suites Stamford

Hampton Inn & Suites Stamford

Hampton Inn & Suites Stamford
2.5 star property
West Side
8.6 out of 10, Excellent, (1004)
Enjoy convenient access to the Stamford Transportation Center, just a 13-minute walk away. This hotel features fitness facilities, restaurant dining, and a relaxing bar. Museum of Black World War II History and local arts venues await nearby exploration.
"Good one night stay "
United States
Aaron
The price is ₩228,158
₩262,381 total
includes taxes & fees
Dec 26 - Dec 27
Hampton Inn & Suites Stamford
View from property
Residence Inn Stamford Downtown

Residence Inn Stamford Downtown

Residence Inn Stamford Downtown
3.0 star property
Downtown Stamford
9.4 out of 10, Exceptional, (374)
Convenient to the train station, this hotel offers a free breakfast and beach shuttle. Guests can enjoy the indoor pool or visit the on-site bar after a workout in the 24-hour fitness center. Nearby attractions include Stamford Center for the Arts.
"Room was great. Clean comfortable bed. Complimentary breakfast was weak. Need omelet station, cut fruit and decent yogurt. "
United States
Michael
The price is ₩370,905
₩426,540 total
includes taxes & fees
Dec 21 - Dec 22
Residence Inn Stamford Downtown
Reception
DoubleTree by Hilton Stamford

DoubleTree by Hilton Stamford

DoubleTree by Hilton Stamford
3.5 star property
Waterside
7.4 out of 10, Good, (1006)
Just steps from Stamford Transportation Center, this contemporary hotel offers a relaxing indoor pool and dining at Tavola Restaurant. A 24-hour health club and bar enhance your stay near Stamford Center for the Arts.
"We’ve stayed here a few times Overall it’s good!"
United States
Lisa
The price is ₩189,147
₩217,519 total
includes taxes & fees
Jan 4 - Jan 5, 2026
DoubleTree by Hilton Stamford
Lobby
The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference
2.5 star property
Ridgeway-Bullshead
7.8 out of 10, Good, (700)
Centrally positioned near Hand & Stone Massage and E. Gaynor Brennan Golf Course, this hotel offers a rejuvenating indoor pool, relaxing hot tub, and sauna. Enjoy free breakfast at Ricotta restaurant and maintain routines in the 24-hour fitness center, all with attentive service.
"I stayed here 2 days for work and it waa perfect. Quiet, clean, well sraffed. "
United States
Keith
The price is ₩218,110
₩250,826 total
includes taxes & fees
Dec 18 - Dec 19
The Armon Stamford Hotel & Conference
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)
This charming riverside hotel offers complimentary Wi-Fi, parking, and on-the-go breakfast. Located near the train station and just a 15-minute walk to Peekskill, with kayaking and mountain biking nearby. Rooms include refrigerators and microwaves.
"Always a pleasant place "
United States
Abner
The price is ₩131,516
₩150,416 total
includes taxes & fees
Dec 21 - Dec 22
Inn on the Hudson
Front of property - evening/night
Stamford Marriott Hotel & Spa

Stamford Marriott Hotel & Spa

Stamford Marriott Hotel & Spa
3.5 star property
Downtown Stamford
8.0 out of 10, Very Good, (1006)
Located near Stamford Town Center and metro station, this hotel offers a full-service spa with massages and aromatherapy. Enjoy American cuisine at Sam's Bistro, workout at the fitness center, or relax at the bar. Guests consistently praise the attentive service.
"Always a good time at the Stamford Marriott"
United States
OUIDA
The price is ₩287,636
₩330,782 total
includes taxes & fees
Dec 20 - Dec 21
Stamford Marriott Hotel & Spa
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

This historic former stagecoach stop serves exceptional American and German cuisine in elegant, fireplace-lit dining rooms. Stroll through the landscaped gardens with waterfalls before your memorable meal.
See properties
Lovely spot in Westchester, NY
Photo by louann ohora
Open Photo by louann ohora

Teatown Lake Reservation

This 1,000-acre nature preserve features diverse ecosystems along scenic trails. Explore the floating boardwalk across the lake for wildlife viewing and see the island's native wildflower collection.
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

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

10/10 Excellent
"Clean and comfortable room. Had a room on a non smoking floor which was good. Several people out front entrance smoking different stuff so had to walk through a cloud upon entering.. Needed something to avoid snowy travel and it fit the bill!"
Beatrice 1-night trip
Posted 17 hours ago
Hampton Inn White Plains/Tarrytown

More cheap stays in Ossining

Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

160 Corporate Blvd Yonkers NY
The price is ₩143,042 per night from Jan 4 to Jan 5
₩143,042
₩168,414 total
Jan 4 - Jan 5, 2026
includes taxes & fees
8.2/10 Very Good! (1,660 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 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 Sonesta White Plains Downtown. See all available top hotels, or vacation rentals in Ossining.
What are some of the best vacation rentals that Ossining has to offer?
3BR Prime Luxury near NYC w Arcade Room: You might want to consider this vacation 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. 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: Offers daily, an indoor pool, and complimentary wired internet access. Sonesta White Plains Downtown and DoubleTree by Hilton Hotel Nanuet 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. In Ossining, there are 13 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.

Explore a world of travel with Expedia