Hotels in Ossining

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Top 5 hotels in Ossining at a glance

Windrose On Hudson — 3-star hotel in Ossining. Guest rating: 8.6/10 — Excellent.
Summer Pool Oasis Custom Bar Arcade Pool Table — 2-star hotel in Ossining.
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG — 2.5-star hotel in Hawthorne. Guest rating: 9.0/10 — Wonderful.
Baymont by Wyndham White Plains - Elmsford — 2.5-star hotel in Elmsford. Guest rating: 8.4/10 — Very Good.
SpringHill Suites by Marriott Tarrytown Westchester County — 3-star hotel in Tarrytown. Guest rating: 8.8/10 — Excellent.

Where to stay in Ossining?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Ossining on Hotels.com. These Ossining hotels consistently deliver on comfort, location and traveler experience. Last updated on August 14, 2026.

Room, 1 Queen Bed, Mobility Accessible | Desk, laptop workspace, iron/ironing board, cribs (free)

Windrose On Hudson

Ossining

CNY1,043

CNY1,161 total

includes taxes & fees

Aug 16 - Aug 17

Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

CNY5,641

CNY9,480 total

includes taxes & fees

Sep 13 - Sep 14

In-room safe, soundproofing, iron/ironing board, WiFi (free)

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Hawthorne

CNY796

CNY910 total

includes taxes & fees

Aug 30 - Aug 31

Desk, laptop workspace, blackout drapes, iron/ironing board

Baymont by Wyndham White Plains - Elmsford

Elmsford

CNY889

CNY1,016 total

includes taxes & fees

Aug 31 - Sep 1

Hypo-allergenic bedding available, desk, iron/ironing board

SpringHill Suites by Marriott Tarrytown Westchester County

Tarrytown

CNY1,087

CNY1,243 total

includes taxes & fees

Aug 30 - Aug 31

Courtyard by Marriott Tarrytown Westchester County

Tarrytown

CNY969

CNY1,108 total

includes taxes & fees

Aug 30 - Aug 31

Westchester Marriott

Tarrytown

CNY1,198

CNY1,370 total

includes taxes & fees

Aug 16 - Aug 17

Standard Room, 2 Double Beds, Non Smoking | Desk, iron/ironing board, WiFi (free), alarm clocks

FairBridge Inn Express Nyack

Nyack

CNY668

CNY797 total

includes taxes & fees

Aug 16 - Aug 17

Tarrytown House Estate

Tarrytown

CNY1,073

CNY1,395 total

includes taxes & fees

Aug 23 - Aug 24

Residence Inn Orangeburg

Orangeburg

CNY1,087

CNY1,210 total

includes taxes & fees

Aug 20 - Aug 21

Indoor pool, open 8:30 AM to 9:30 PM, sun loungers

DoubleTree by Hilton Hotel Nanuet

Nanuet

CNY785

CNY914 total

includes taxes & fees

Sep 13 - Sep 14

Hampton Inn White Plains/Tarrytown

Elmsford

CNY763

CNY873 total

includes taxes & fees

Aug 23 - Aug 24

Cambria Hotel & Suites - White Plains Downtown

White Plains

CNY1,236

CNY1,413 total

includes taxes & fees

Sep 3 - Sep 4

In-room safe, desk, iron/ironing board, cribs (free)

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

Peekskill

CNY877

CNY1,003 total

includes taxes & fees

Sep 13 - Sep 14

Seasonal outdoor pool, open 11:00 AM to 8:00 PM, sun loungers

Hotel MTK Mount Kisco

Mount Kisco

CNY990

CNY1,132 total

includes taxes & fees

Aug 23 - Aug 24

Hilton Garden Inn Westchester Dobbs Ferry, NY

Dobbs Ferry

CNY879

CNY1,006 total

includes taxes & fees

Aug 30 - Aug 31

Premium bedding, pillowtop beds, in-room safe, desk

Hotel Nyack, a JdV by Hyatt Hotel

Nyack

CNY846

CNY1,151 total

includes taxes & fees

Aug 20 - Aug 21

Element by Marriott Spring Valley

Spring Valley

CNY938

CNY1,091 total

includes taxes & fees

Aug 23 - Aug 24

Days Inn by Wyndham Elmsford / White Plains

Elmsford

CNY719

CNY846 total

includes taxes & fees

Aug 23 - Aug 24

Sleepy Hollow Hotel, a Dolce by Wyndham

Tarrytown

CNY1,014

CNY1,160 total

includes taxes & fees

Aug 24 - Aug 25

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Go beyond your typical stay in Ossining

Apartment

Family friendly

Spa

Hot tub

Pool

Pet friendly

Top landmarks in Ossining

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

Travelers Rest

If you're looking for things to do when staying in Ossining, go to Travelers Rest.

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A misty lake surrounded by trees with sunlight filtering through the leaves.

Teatown Lake Reservation

If you'd like to get a taste of Ossining student life, check out Teatown Lake Reservation, located 3.8 mi (6.1 km) from central Ossining. Why not take a stroll along the riverfront and watch the sunset while you're here? Want to stretch your legs some more? Head to Croton Point Park and Kitchawan Preserve, both nearby.

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Sing Sing Correctional Facility

Sing Sing Correctional Facility is worth a visit, located 0.7 mi (1.2 km) from central Ossining. Why not take a stroll along the riverfront and watch the sunset while you're here? It's also full of great shops and restaurants, so you can spend the afternoon having a wander.

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Thomas J. Watson Research Center

If seeing the sights is on your list of things to do, head to Thomas J. Watson Research Center— just one of the landmarks located 4.4 mi (7.1 km) from central Ossining. Why not take a stroll along the riverfront and watch the sunset while you're here?

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Ossining Public Library

If you're planning a bit of sightseeing during your trip, head to Ossining Public Library— just one of the monuments in central Ossining.

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Sing Sing Prison Museum

If visiting museums in Ossining are on your list, you might want to check out the upcoming exhibitions at Sing Sing Prison Museum, located in the heart of town. Why not take a stroll along the riverfront and watch the sunset while you're here? If you want to see more of the museums in Ossining, Ossining Historical Society isn't far either.

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Kitchawan Preserve

Kitchawan Preserve is 5.5 mi (8.9 km) from central Ossining, why not stop by during your stay. Why not take a stroll along the riverfront and watch the sunset while you're here? Want to stretch your legs some more? Head to Teatown Lake Reservation and Ossining Dog Park, both nearby.

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Depot Square

Depot Square is 0.5 mi (0.8 km) from central Ossining, why not stop by during your stay. Why not take a stroll along the riverfront and watch the sunset while you're here? Want to stretch your legs some more? Head to Louis Engel Waterfront Park and Pleasant Square, both a short walk away.

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Learn more about Ossining

Infamous Sing Sing Prison Museum offers a fascinating glimpse into America's most notorious correctional facility, where history feels eerily present. Louis Engel Waterfront Park provides a refreshing contrast with Hudson River views that make you forget what's just up the hill. The Ossining Historical Society reveals small-town America with unexpected depth and quirky artifacts. Teatown Lake Reservation offers trails where city stress evaporates among pristine forests surprisingly close to New York City. Depot Square buzzes with locals who've perfected small-town conversation while maintaining their metropolitan edge. The Thomas J. Watson Research Center stands as a modernist monument to big thinking in a village balancing prison history with cultural richness.

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A historic stone building with a large circular window and a tower with a green roof.

Check out reviews of Ossining hotels guests love

Hotel Nyack, a JdV by Hyatt Hotel

8/10 Good

"Great experience. Couples weekend. Great Breakfast and better Happy Hour. Fully stocked Mini Bar.."

LIV Hotel Bronx - Newly Built

8/10 Good

"Close to Little Italy and the Botanical Garden. No free parking available. Had to park at a valet parking garage 1/4 mile away. First room door would not lock. Got a new room. No safe to store my laptop.Had to double park to load my luggage."

Tarrytown House Estate

10/10 Excellent

"The grounds are absolutely beautiful with lots to do. Unfortunately we were only in for a quick overnight so we couldn’t enjoy anything but I would go back again!"

Sleepy Hollow Hotel, a Dolce by Wyndham

8/10 Good

"Great experience"

Hilltop Inn & Suites

10/10 Excellent

"nice place"

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

8/10 Good

"The room was clean, getting checked in by the snippy staff wasn’t quite the experience I thought it would be. While waiting quite a long time to get checked in because no one was at the front desk, and no way to contact any one, we looked up google reviews and saw some rather bad ones. Thinking there’s no way that what they wrote about could be true- like rude counter staff or cleaning crews that completely ignore the do not disturb sign.. both occurred in the ONE night we stayed. The whole hotel seemed to be undergoing maintenance and renovation as well, there were projects started all over with no real organization to any of it. It was a very odd experience overall. But for a cheap quick option, it was satisfactory. Surprisingly quiet for literally being next to the highway too."

Frequently asked questions

How much does a hotel room cost in Ossining?

You can choose a great hotel in Ossining from CNY764 with properties to suit all budgets and needs. If you're looking for an affordable hotel in Ossining that meets all of your requirements, just sort hotels by "Price: low to high" after applying your filters when searching on Hotels.com.

How can I find deals and earn rewards at Ossining hotels?

Discover great deals on Ossining hotel stays with Hotels.com. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If it's a spontaneous trip, check out our last-minute deals on Ossining hotels.

Can I book Ossining hotels with free cancellation?

In order to book a refundable Ossining hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". Many hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are some of the best Ossining hotels with free parking?

If you're arriving by car, choosing a great Ossining hotel with free parking is a plus. Our travelers' favorites include:

Windrose On Hudson: A hotel with an average guest rating of 8.6 out of 10

What are some popular hotels in central Ossining?

For hotels in central Ossining, check out Hotel Nyack, a JdV by Hyatt Hotel and Windrose On Hudson. Travelers love Hotel Nyack, a JdV by Hyatt Hotel for its location, as well as the seasonal outdoor pool, hot tub and restaurant this hotel offers. Windrose On Hudson is another popular central hotel with a bar/lounge, a coffee shop/cafe and karaoke. Downtown Tarrytown is a central neighborhood for your Ossining vacation.

What accommodations do travelers recommend in Ossining?

Guests like Windrose On Hudson, Tarrytown House Estate and Armoni Inn & Suites.

Can I book refundable accommodations in Ossining?

If you need the flexibility to change your plans to Ossining, most properties provide refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Ossining if I want a vacation rental instead of a hotel?

Browse 8 vacation homes on our site.

What will the weather in Ossining be like during my trip?

The warmest months in Ossining are usually July and August with an average temp of 71°F. January and February are the chilliest months when the average temp is 34°F. The rainiest months are July and October.

Why should I book my Ossining accommodation with Hotels.com?

There are lots of reasons to book your Ossining trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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