Hotels in Ossining
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Sep 5 - Sep 6Tomorrow
Sep 6 - Sep 7Next weekend
Sep 11 - Sep 13In two weeks
Sep 18 - Sep 20Where to stay in Ossining?
Windrose On Hudson
Windrose On HudsonOssining
$213
$237 total
includes taxes & fees
Sep 6 - Sep 7
Summer Pool Oasis Custom Bar Arcade Pool Table
Summer Pool Oasis Custom Bar Arcade Pool TableOssining
$659
$1,233 total
includes taxes & fees
Sep 8 - Sep 9
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Holiday Inn Express & Suites Hawthorne Elmsford North by IHGHawthorne
$139
$159 total
includes taxes & fees
Sep 20 - Sep 21
Baymont by Wyndham White Plains - Elmsford
Baymont by Wyndham White Plains - ElmsfordElmsford
$127
$145 total
includes taxes & fees
Sep 13 - Sep 14
West Gate Inn Nyack
West Gate Inn NyackNyack
$99
$113 total
includes taxes & fees
Sep 6 - Sep 7
SpringHill Suites by Marriott Tarrytown Westchester County
SpringHill Suites by Marriott Tarrytown Westchester CountyTarrytown
$130
$148 total
includes taxes & fees
Sep 13 - Sep 14
Hampton Inn White Plains/Tarrytown
Hampton Inn White Plains/TarrytownElmsford
$113
$129 total
includes taxes & fees
Sep 13 - Sep 14
Courtyard by Marriott Tarrytown Westchester County
Courtyard by Marriott Tarrytown Westchester CountyTarrytown
$161
$184 total
includes taxes & fees
Sep 13 - Sep 14
DoubleTree by Hilton Hotel Nanuet
DoubleTree by Hilton Hotel NanuetNanuet
$118
$137 total
includes taxes & fees
Sep 20 - Sep 21
Hotel Nyack, a JdV by Hyatt Hotel
Hotel Nyack, a JdV by Hyatt HotelNyack
$127
$172 total
includes taxes & fees
Sep 13 - Sep 14
Sheraton Tarrytown Hotel
Sheraton Tarrytown HotelTarrytown
$161
$184 total
includes taxes & fees
Sep 6 - Sep 7
Tarrytown House Estate
Tarrytown House EstateTarrytown
$179
$230 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHGPeekskill
$136
$156 total
includes taxes & fees
Sep 8 - Sep 9
Hotel MTK Mount Kisco
Hotel MTK Mount KiscoMount Kisco
$163
$187 total
includes taxes & fees
Sep 13 - Sep 14
Sleepy Hollow Hotel, a Dolce by Wyndham
Sleepy Hollow Hotel, a Dolce by WyndhamTarrytown
$137
$157 total
includes taxes & fees
Oct 5 - Oct 6
Westchester Marriott
Westchester MarriottTarrytown
$186
$213 total
includes taxes & fees
Sep 6 - Sep 7
Tappan Zee Hotel
Tappan Zee HotelWest Nyack
$95
$110 total
includes taxes & fees
Sep 6 - Sep 7
Hampton Inn Nanuet
Hampton Inn NanuetNanuet
$106
$123 total
includes taxes & fees
Sep 13 - Sep 14
Hilton Garden Inn Nanuet
Hilton Garden Inn NanuetNanuet
$104
$121 total
includes taxes & fees
Sep 14 - Sep 15
Inn on the Hudson
Inn on the HudsonPeekskill
$93
$106 total
includes taxes & fees
Sep 13 - Sep 14
Go beyond your typical stay in Ossining
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Apartment
Family friendly
Our prices for hotels in Ossining are cheapest in December
Our prices for hotels in Ossining are cheapest in December
Price trends for hotels in Ossining
Pricing is based on two traveler single night rates
Top landmarks in Ossining
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 Croton Landing Park, both nearby.
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.
Hudson Hills Golf Course
You might want to play some rounds at Hudson Hills Golf Course, located 3.3 mi (5.3 km) from central Ossining. Why not take a stroll along the riverfront and watch the sunset while you're here? If Hudson Hills Golf Course doesn't quite scratch your golfing itch, Mohansic Golf Course and Rockland Lake State Park Championship Golf Course are all just a short drive away.
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.
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?
Nelson Park
Nelson Park 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?
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.
Merchants Square
9.0/10 (2 reviews)
If you like spending time outside, why not spend the afternoon at Merchants Square, a park in the heart of 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 Pleasant Square and Depot Square, both a short walk away.
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.
See all hotels in Ossining
Photo by louann ohora
Check out reviews of Ossining hotels guests love
LIV Hotel Bronx - Newly Built
10/10 Excellent
"it was a nice stay wasn’t too far from anything and the train station was close"
Hampton Inn White Plains/Tarrytown
8/10 Good
"Great stay"
Royal Regency Hotel
8/10 Good
"Stayed here back in 1998, wedding night. Fast forward to 2026, and I have stayed twice in 2 months. Breakfast is sweet and the rooms are pleasant. The restaurant is great also. Great bang for your buck!!!"
Crowne Plaza Suffern - Mahwah by IHG
10/10 Excellent
"Muy lindo hotel, limpio y con gran desayuno. El hall es impresionante y los jardines muy lindos. El gym chico pero sirve. Le falta a la zona un poco mas de opciones de comida. Pero vale la pena."
Hotel Nyack, a JdV by Hyatt Hotel
10/10 Excellent
"Beds so comfy and love the bathroom layout"