Photo by louann ohora

Ossining hotels from HK$667

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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Ossining hotels

Windrose On Hudson

Windrose On Hudson
3.0 star property
Ossining
8.2 out of 10, Very good, (104)
"Clean room, staff were very welcoming"
United States
Semaj
The price is HK$1,443
HK$1,607 total
includes taxes & fees
7 Jan - 8 Jan 2026
Windrose On Hudson

Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
Ossining
The price is HK$2,980
HK$6,981 total
includes taxes & fees
5 Jan - 6 Jan 2026
Foliage at Westchester Manor - Near Sleepy Hollow

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1004)
"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 HK$787
HK$891 total
includes taxes & fees
27 Dec - 28 Dec
Overlook Lodge at Bear Mountain

Inn on the Hudson

Inn on the Hudson
2.0 star property
Peekskill
7.0 out of 10, Good, (1001)
"yes but the beds were not comfortable"
United States
Gene
The price is HK$692
HK$792 total
includes taxes & fees
28 Dec - 29 Dec
Inn on the Hudson

Red Carpet Inn

Red Carpet Inn
2.0 star property
Cove - East Side - Shippan
6.4 out of 10, (1001)
"It seemed a little bit cleaner since the last couple of times ive been there"
United States
Melissa
The price is HK$613
HK$706 total
includes taxes & fees
25 Dec - 26 Dec
Red Carpet Inn

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, (1036)
"The location is great and convenient! The staff is very kind and attentive!"
United States
Cruz
The price is HK$700
HK$805 total
includes taxes & fees
18 Jan - 19 Jan 2026
La Quinta Inn & Suites by Wyndham Stamford / New York City

Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester
2.0 star property
Ardsley
8.6 out of 10, Excellent, (1000)
"Room clean, staff kind, accommodations nice, location fine."
United States
Daniel
Ardsley Acres Hotel Westchester

The Abbey Inn & Spa

The Abbey Inn & Spa
4.0 star property
Peekskill
9.2 out of 10, Wonderful, (231)
"We had a very short stay but what i can say is that rooms were extremely clean, the staff was beyond courteous extremely helpful restaurants was not only beautiful but food services once again amazing.. We look foward to coming back for a longer stay and try the spa out as well.."
United States
Paul
The price is HK$1,956
HK$2,594 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Abbey Inn & Spa

Super 8 by Wyndham Mahwah

Super 8 by Wyndham Mahwah
2.5 star property
Mahwah
7.4 out of 10, Good, (1001)
"Room was very spacious and the staff was extremely helpful!!!!"
United States
Lydia
The price is HK$582
HK$667 total
includes taxes & fees
4 Jan - 5 Jan 2026
Super 8 by Wyndham Mahwah

DoubleTree by Hilton Mahwah

DoubleTree by Hilton Mahwah
4.0 star property
Mahwah
7.8 out of 10, Good, (936)
"Easy check in."
United States
Nancy
The price is HK$886
HK$1,016 total
includes taxes & fees
7 Jan - 8 Jan 2026
DoubleTree by Hilton Mahwah

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, (431)
"Beautiful hotel and lovely staff"
United States
Theodóra
The price is HK$1,249
HK$1,437 total
includes taxes & fees
2 Jan - 3 Jan 2026
The Lloyd Stamford, Tapestry Collection by Hilton

Courtyard by Marriott Mahwah

Courtyard by Marriott Mahwah
3.0 star property
Mahwah
8.2 out of 10, Very good, (1000)
"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 HK$832
HK$954 total
includes taxes & fees
28 Dec - 29 Dec
Courtyard by Marriott Mahwah

Courtyard by Marriott Stamford Downtown

Courtyard by Marriott Stamford Downtown
3.0 star property
Downtown Stamford
9.0 out of 10, Wonderful, (839)
"Super attentive staff and very welcoming! Clean and moderately quiet for its central location!"
United States
TIFFANI
The price is HK$1,672
HK$1,923 total
includes taxes & fees
1 Jan - 2 Jan 2026
Courtyard by Marriott Stamford Downtown

Royal Regency Hotel

Royal Regency Hotel
3.5 star property
Northwest Yonkers
8.4 out of 10, Very good, (2433)
"Clean room, great breakfast and great service. "
United States
Karen
The price is HK$693
HK$856 total
includes taxes & fees
4 Jan - 5 Jan 2026
Royal Regency Hotel

HYATT house White Plains

HYATT house White Plains
3.0 star property
West Harrison
8.6 out of 10, Excellent, (1012)
"Great hotel"
United States
Tom
The price is HK$1,362
HK$1,557 total
includes taxes & fees
25 Dec - 26 Dec
HYATT house White Plains

Hampton Inn & Suites Stamford

Hampton Inn & Suites Stamford
2.5 star property
West Side
8.6 out of 10, Excellent, (1001)
"Good one night stay "
United States
Aaron
The price is HK$1,295
HK$1,490 total
includes taxes & fees
18 Jan - 19 Jan 2026
Hampton Inn & Suites Stamford

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, (1001)
"I highly recommend this hotel. "
United States
Leigh
The price is HK$949
HK$1,085 total
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG

DoubleTree by Hilton Stamford

DoubleTree by Hilton Stamford
3.5 star property
Waterside
7.4 out of 10, Good, (1004)
"Overall it was a good place to stay"
United States
Jacqueline
The price is HK$1,051
HK$1,209 total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Stamford

Super 8 by Wyndham Stamford/New York City Area

Super 8 by Wyndham Stamford/New York City Area
2.5 star property
West Side
6.4 out of 10, (1002)
"The hotel was affordable and suited our needs for our quick one night stopover. Staff was helpful, breakfast was good - we were happy with the experience."
United States
Peter
The price is HK$760
HK$874 total
includes taxes & fees
19 Jan - 20 Jan 2026
Super 8 by Wyndham Stamford/New York City Area

Amsterdam Hotel

Amsterdam Hotel
2.0 star property
Downtown Stamford
8.4 out of 10, Very good, (1728)
"Excellent stay! Nice and comfortable…quiet…it had everything that we needed! "
Canada
MARTHA PATRICIA
Amsterdam Hotel
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.
Save an average of 15% on thousands of hotels when you're signed in

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.

Main building at Maryknoll
Photo by louann ohora
Open Photo by louann ohora

Top Ossining Hotel Reviews

More cheap stays in Ossining

Hotels in Ossining with star-rating

Find out more about Ossining

Top reasons to visit Ossining

  • Outdoor Adventures: Ossining boasts a variety of urban parks and nature reserves, perfect for exploring the area's natural beauty.
  • Family-Friendly Activities: The town offers numerous engaging activities suitable for families, ensuring memorable experiences for all ages.
  • Cultural Experiences: Visitors can enjoy local theatrical performances and immerse themselves in the rich heritage of the region.
  • Charming Neighbourhoods: Stroll through welcoming neighbourhoods filled with friendly locals, creating a warm atmosphere for tourists.
  • Diverse Accommodation Options: From quaint bed and breakfasts to modern hotels, Ossining provides a range of stays to suit all preferences.

Find great hotels near Ossining

Ossining offers a delightful array of accommodation options, ranging from charming bed and breakfasts to modern hotels. Whether you're seeking pet-friendly facilities or a welcoming atmosphere for LGBTQIA travellers, you'll find suitable choices. Notable options include Abba Hotels, Abbey Inn, and AC Hotels, catering to both leisure and business needs. Explore accommodation rates to ensure a stay that meets your requirements while enjoying the picturesque surroundings of this quaint New York town.

  • Ramada by Wyndham Rochelle Park Near Paramus: Situated a convenient 33.8km from Ossining, the Ramada by Wyndham Rochelle Park Near Paramus offers a blend of comfort and versatility for all types of travellers. The hotel features on-site dining options, including a restaurant that serves daily meals and a welcoming bar and lounge area. Guests can indulge in a complimentary buffet breakfast to start their day, while fitness enthusiasts will appreciate the available fitness facilities. Entertainment is plentiful with televisions featuring premium channels and cable TV. The hotel’s proximity to local metro stations and shopping districts makes it an excellent choice for those keen on exploring the area.
  • Amsterdam Hotel: Located 30.6km away from Ossining, the Amsterdam Hotel caters specifically to business travellers seeking a productive and comfortable stay. This hotel is equipped with essential amenities that facilitate a seamless business experience, making it an ideal choice for those visiting the area for work-related purposes. The focus on providing a professional environment ensures guests can unwind after a long day while being close to key business hubs.
  • Baymont by Wyndham White Plains - Elmsford: Positioned a mere 11.3km from Ossining, the Baymont by Wyndham White Plains - Elmsford is the perfect destination for families and business travellers alike. This hotel is particularly family-friendly, offering amenities tailored for children, such as complimentary cribs and a first aid kit for peace of mind. Guests can enjoy a comfortable stay with a variety of services designed to cater to both leisure and professional needs, making it a versatile choice for all visitors.

Where to stay near Ossining

Ossining, New York, offers a delightful blend of outdoor adventures and family-friendly activities, making it an ideal getaway for various travellers. Explore charming neighbourhoods and immerse yourself in the welcoming atmosphere created by friendly locals. Nearby, you can discover romantic spots and relaxing retreats, perfect for unwinding after a day of exploration. With its unique vibes, Ossining is a wonderful destination for those seeking both city excitement and serene escapes.

  • Millwood: Located a mere 6.4km from Ossining, Millwood offers a delightful blend of outdoor adventures and cultural experiences. This charming city attracts visitors year-round, with peak travel occurring in January to February and September. Families flock to Millwood for its educational venues, music concerts, and recreational areas. History enthusiasts will appreciate proximity to a historic college university and a sports facility stadium. Whether you're hiking in the great outdoors or enjoying a local concert, Millwood has something for everyone.
  • Congers: Also situated 6.4km from Ossining, Congers is a vibrant city that attracts a moderate flow of visitors throughout the year, peaking in April and June to July. This locale is perfect for families seeking an outdoor escape and a touch of city life. With shopping areas and a nearby golf course, there’s plenty to keep visitors entertained. The modern square and tourist precinct add to the city’s appeal, making Congers a fantastic spot for those looking to combine leisure and local culture.
  • Sleepy Hollow: Just 8.0km from Ossining, the quaint village of Sleepy Hollow is famed for its seasonal charm, drawing visitors particularly from August to October. Known for its romantic atmosphere, Sleepy Hollow offers outdoor activities, shopping areas, and local theatres. Nature lovers will enjoy the serene lakes and historic landmarks that dot the landscape. This village is steeped in legend and lore, making it a captivating destination for families and couples alike. Experience the enchanting spirit of Sleepy Hollow during your visit.

Things to do in and around Ossining

Ossining offers a delightful blend of outdoor and family-friendly activities, making it an ideal destination for city-themed vacations. Visitors can explore local shopping areas, enjoy theatrical performances, and even partake in skiing during the winter months. With a variety of family outings and engaging activities, Ossining is a charming spot for those looking to create lasting memories.

Shopping

Ossining offers delightful shopping experiences with local boutiques and markets. For a broader selection, if you're up for a drive, visit The Westchester Mall, located 17.7km away, or Woodbury Common Premium Outlets, 27.4km away, both featuring a mix of entertainment and family-friendly vibes.

Recreation

The Tarrytown Music Hall, a charming venue 9.7km from Ossining, offers vibrant concerts that uplift the spirit. Close by, the Hudson Hills Golf Course provides a refreshing outdoor experience for golf enthusiasts. Meanwhile, the serene Brinton Brook Sanctuary, 8.0km away, invites relaxation amidst nature's tranquillity.

Adventure

Palisades Climb Adventure, located 11.3km from Ossining, offers an exhilarating zipline and ropes course experience amidst stunning outdoor scenery. For hiking enthusiasts, the Orange Trailhead, also 11.3km away, provides scenic trails perfect for exploration. Finally, Grand Prix New York, 12.9km from Ossining, promises thrilling karting adventures.

Nightlife

Ossining's nightlife offers a delightful blend of culture and adventure. Enjoy a romantic evening at the Paramount Hudson Valley Theater, or delve into fun at Legoland Discovery Center Westchester. For more entertainment, the Capitol Theatre promises an engaging atmosphere, perfect for a memorable night out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Ossining

To save money on your trip to Ossining, consider visiting between January and March for lower accommodation rates. Booking your hotel around a month in advance can secure better deals, with Sundays being the cheapest night to stay. Utilise Expedia’s search tool to filter by budget and sort prices from lowest to highest, and look for package deals that combine hotel, flights, and activities for additional savings. For public transport, take advantage of the local bus system, which is cost-effective for getting around. Explore free activities, such as local parks and scenic walks, to further enhance your experience without breaking the bank.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Ossining are January to March, where the prices are slightly lower. This is in comparison to September to October and December, where prices are slightly higher.
  • The best time to book a hotel: Book your hotel in Ossining about 1 month out to secure some of the cheapest prices. If you're the spontaneous type, Expedia's last minute deals and discounts are indicated via the green label below the price.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Ossining is Sunday. The most expensive day to stay in Ossining is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia's search tool to refine your preferences, such as your budget, preferred location, and the type of hotel you desire. To discover the most affordable prices and offers, sort the price filter from lowest to highest.
  • Consider bundling your trip: You can enjoy savings by combining your Ossining hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions near Ossining

Ossining offers a delightful blend of outdoor adventures and cultural experiences, making it perfect for families and city-themed holidays. Visitors can explore urban parks, modern colleges and universities, as well as nature reserves. The diverse points of interest cater to travellers seeking a family-friendly atmosphere while enjoying the area's natural beauty and rich heritage.

  • Van Cortlandt Manor: This historic house offers a glimpse into 18th-century life, surrounded by beautifully landscaped gardens. Visitors can explore its fascinating architecture and enjoy various cultural events throughout the year.
  • Kykuit: The former estate of the Rockefellers, Kykuit is renowned for its stunning gardens and impressive art collection. Guided tours reveal the grandeur of this historic building and its rich history.
  • Old Dutch Church of Sleepy Hollow: A charming church steeped in history, this site features beautiful stained glass and an enchanting graveyard. It’s a perfect spot to appreciate the local culture and heritage.

Best time to go to Ossining

The best time to visit Ossining is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January30.0°F (-1.1°C)Light RainMostly SunnySlightly LowSlightly Low
February31.6°F (-0.2°C)Light RainMostly SunnySlightly LowSlightly Low
March38.8°F (3.8°C)Light RainMostly SunnyAverageSlightly Low
April49.8°F (9.9°C)Light RainMostly SunnySlightly HighAverage
May60.1°F (15.6°C)Light RainMostly SunnyAverageAverage
June68.9°F (20.5°C)Light RainMostly SunnyAverageAverage
July75.6°F (24.2°C)Light RainMostly SunnySlightly HighAverage
August73.9°F (23.3°C)Light RainMostly SunnyAverageAverage
September66.9°F (19.4°C)Light RainMostly SunnySlightly HighSlightly High
October56.1°F (13.4°C)Light RainMostly SunnyAverageSlightly High
November44.2°F (6.8°C)Light RainMostly SunnyAverageAverage
December36.3°F (2.4°C)Light RainMostly SunnySlightly LowSlightly High

The nearest major airports for your trip to Ossining

Ossining, New York, is conveniently accessible from three major airports. John F. Kennedy International Airport (JFK) is situated 57.9km away, with luxurious hotel options like the 5-star Arlo Williamsburg and The William Vale, both 17.7km from the airport. Newark Liberty International Airport (EWR) lies 59.5km from Ossining, featuring nearby hotels such as the 5-star Dominick and The Beekman, A Thompson Hotel, both 14.5km away. LaGuardia Airport (LGA) is the closest at 43.5km, offering elegant accommodations like Virgin Hotels New York City and The Plaza, both within 9.7km. Each airport has accessible transport options from these hotels.

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 Baymont by Wyndham White Plains - Elmsford and Ramada by Wyndham Bronx. 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?
Baymont by Wyndham White Plains - Elmsford: Offers daily, an indoor pool and complimentary high-speed (wired) Internet access. Sonesta White Plains Downtown and DoubleTree by Hilton Hotel Nanuet 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 12 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