Ossining, NY

Travel Guide

A wooden boardwalk winding through a forest with autumn foliage.
A lake surrounded by autumn-colored trees and houses on a hillside.
A wooden bridge over a lake with a sign reading "BERGMANN BOARDWALK".
A row of historic buildings with distinct architectural styles, including a red brick building with a clock tower and a white building with ornate detailing.
A sunset over a calm lake with several boats anchored.
Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
$164 nightly
The price is $183 total per night from Nov 15 to Nov 16
$183 total
Nov 15 - Nov 16
Total with taxes and fees
Book a stay at this business-friendly hotel in Ossining. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Van Cortlandt Manor and ...
8.6/10 Excellent! (283 reviews)
"An amazing experience for us all-around..........Thank You. We'll see You again."

Reviewed on Nov 4, 2026

Windrose On Hudson
LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

3 out of 5
3530 Webster Ave Bronx NY
$138 nightly
The price is $162 total per night from Dec 1 to Dec 2
$162 total
Dec 1 - Dec 2
Total with taxes and fees
Stay at this hotel in Bronx. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Yankee Stadium and Bronx Zoo are located nearby.
7.2/10 Good! (1,235 reviews)
"The hotel is fairly new and Im sure they are still working out the kinks. There was no iron/ironing board, or microwave available. I did feel a little uneasy due to I couldn't deadbolt lock my door. The deadbolt lock and hole didn't match so I only had the latch to secure. Just a little noisy so ..."

Reviewed on Nov 4, 2026

LIV Hotel Bronx - Newly Built
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd Yonkers NY
$129 nightly
The price is $152 total per night from Nov 8 to Nov 9
$152 total
Nov 8 - Nov 9
Total with taxes and fees
Book a stay at this business-friendly hotel in Yonkers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant ...
Royal Regency Hotel
See all 1,242 properties in Ossining
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.
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Ossining NY
Stay at this vacation home in Ossining. Enjoy free WiFi, private pools, and a garden. Popular attractions Sing Sing Prison Museum and Louis Engel Waterfront ...
8.8/10 Excellent! (10 reviews)
"We had a wonderful stay at this property and really enjoyed our time there. The house was very clean, comfortable, and well taken care of, which made us feel right at home. The host was also fantastic—very responsive, easy to communicate with, and always quick to answer any questions we had. Everything ..."

Reviewed on Aug 20, 2026

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Stamford Suites

Stamford Suites

4 out of 5
720 Bedford St Stamford CT
Book a stay at this business-friendly aparthotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
6.2/10 (207 reviews)
"Do not come to this place if you are looking for something nice. The room was dusty, smelled weird. I had it booked for 2 nights a d just stayed 1. I rather take the loose than stay there another night. The price is what got me to book this suite. Next time I’ll just pay extra for a different place. ..."

Reviewed on Nov 2, 2026

Stamford Suites
Global Luxury Suites White Plains

Global Luxury Suites White Plains

3.5 out of 5
57 Bank St White Plains NY
Book a stay at this business-friendly apartment in White Plains. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Westchester County ...
Global Luxury Suites White Plains
See all properties in Ossining
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.

Stay near popular Ossining attractions

A dam with a reservoir, surrounded by autumn foliage and hills.

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

Frequently asked questions

When is the best time to visit Ossining?
The best time to visit Ossining is from May through September, when the weather is generally pleasant for outdoor activities. For travelers seeking fewer crowds and better value, the quieter months of December through March are a good option, offering a cooler, more serene experience.
How do you get around Ossining?
In Ossining, travelers can primarily get around using the train, with service available at Ossining Station. This offers a practical way to travel to and from the destination. For exploring areas not reached by train or for more flexible travel, rideshare services are also available.
What cuisines can you find in Ossining?
In Ossining, you can find South American cuisine, offering dishes such as empanadas, ceviche, and lomo saltado. Travelers can also enjoy Mexican food like tacos and burritos, classic Italian dishes, and various Chinese options. Additionally, there are Mediterranean, Spanish, and North American culinary choices available.
Can I book a refundable hotel in Ossining?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Ossining by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Ossining with Expedia?
Expedia makes it easier to plan your Ossining trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Ossining?
The best choice depends on your travel style. Hotels in Ossining can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Ossining trip on Expedia?
Once you've booked your Ossining trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Ossining trip?
Expedia offers customer support before, during, and after your Ossining trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Ossining?
If it's your first trip to Ossining, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Ossining hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Ossining hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Ossining

A stone bridge over a stream surrounded by autumn foliage.

Briarcliff Manor

A train station with tracks, a platform, and trees with autumn leaves.

Mount Kisco

A dam with a waterfall, a river, and surrounding hills.

Croton-on-Hudson

A red bridge over a river surrounded by autumn foliage.

Yorktown Heights

Explore a world of travel with Expedia