Photo by louann ohora
Hotels in Ossining
Free cancellation options if plans change
Earn rewards on every night you stay
Save more with Member Prices
Check prices for these dates
Where to stay in Ossining?
Westchester Summer Pool Pet Friendly Events Games
Westchester Summer Pool Pet Friendly Events GamesOssining
The price is $489
$1,006 total
includes taxes & fees
Apr 13 - Apr 14
Windrose On Hudson
Windrose On HudsonOssining
8.4 out of 10, Very Good, (125 reviews)
- Take in Hudson riverside scenes at this Ossining hotel with a fitness center.
The price is $172
$191 total
includes taxes & fees
May 3 - May 4
Red Carpet Inn
Red Carpet InnCove - East Side - Shippan
6.6 out of 10, (1,003 reviews)
- Wake to spacious, comfortable rooms near Stamford's transportation hub.
The price is $83
$95 total
includes taxes & fees
Apr 13 - Apr 14
Amsterdam Hotel
Amsterdam HotelDowntown Stamford
8.4 out of 10, Very Good, (1,743 reviews)
- Experience the quietest retreat close to Stamford Town Center and train station.
The price is $103
$119 total
includes taxes & fees
May 7 - May 8
The Stamford Hotel
The Stamford HotelDowntown Stamford
7.8 out of 10, Good, (1,153 reviews)
- Explore downtown Stamford from this centrally located hotel near the train station.
The price is $182
$209 total
includes taxes & fees
May 11 - May 12
Stamford Marriott Hotel & Spa
Stamford Marriott Hotel & SpaDowntown Stamford
8.0 out of 10, Very Good, (1,001 reviews)
- Convenient Stamford hotel close to metro station with relaxing on-site spa.
The price is $195
$224 total
includes taxes & fees
Apr 16 - Apr 17
Residence Inn Stamford Downtown
Residence Inn Stamford DowntownDowntown Stamford
9.4 out of 10, Exceptional, (390 reviews)
- Convenient train station access with indoor pool and free breakfast in Stamford.
The price is $229
$263 total
includes taxes & fees
Apr 19 - Apr 20
Courtyard by Marriott Stamford Downtown
Courtyard by Marriott Stamford DowntownDowntown Stamford
9.0 out of 10, Wonderful, (855 reviews)
The price is $213
$245 total
includes taxes & fees
Apr 19 - Apr 20
The Lloyd Stamford, Tapestry Collection by Hilton
The Lloyd Stamford, Tapestry Collection by HiltonDowntown Stamford
8.8 out of 10, Excellent, (484 reviews)
- Enjoy stylish accommodations steps from Stamford Transportation Center.
The price is $163
$188 total
includes taxes & fees
Apr 26 - Apr 27
Hampton Inn & Suites Stamford
Hampton Inn & Suites StamfordWest Side
8.6 out of 10, Excellent, (1,002 reviews)
- Experience Stamford with easy train access, fitness center, and a welcoming bar.
The price is $156
$180 total
includes taxes & fees
May 10 - May 11
DoubleTree by Hilton Stamford
DoubleTree by Hilton StamfordWaterside
7.4 out of 10, Good, (1,007 reviews)
- Convenient train-station hotel with indoor pool for business or city exploration.
The price is $158
$182 total
includes taxes & fees
Apr 19 - Apr 20
The Armon Stamford Hotel & Conference
The Armon Stamford Hotel & ConferenceRidgeway-Bullshead
7.8 out of 10, Good, (762 reviews)
- Modern pool and fitness hotel in Stamford with conference center access.
The price is $164
$189 total
includes taxes & fees
Apr 13 - Apr 14
Super 8 by Wyndham Stamford/New York City Area
Super 8 by Wyndham Stamford/New York City AreaWest Side
6.4 out of 10, (1,006 reviews)
- Enjoy convenient train access and daily amenities at this relaxed Stamford hotel.
The price is $89
$103 total
includes taxes & fees
Apr 22 - Apr 23
La Quinta Inn & Suites by Wyndham Stamford / New York City
La Quinta Inn & Suites by Wyndham Stamford / New York CityWaterside
6.8 out of 10, (1,240 reviews)
- Interstate access and convenient Stamford location with an indoor pool year-round.
The price is $100
$115 total
includes taxes & fees
May 3 - May 4
Hyatt Regency Greenwich
Hyatt Regency GreenwichOld Greenwich
8.6 out of 10, Excellent, (1,004 reviews)
The price is $208
$239 total
includes taxes & fees
Apr 23 - Apr 24
Ethan Allen Hotel
Ethan Allen HotelDanbury
8.0 out of 10, Very Good, (1,192 reviews)
- Stay near Danbury Fair Mall with comfortable beds and seasonal poolside lounging.
The price is $116
$134 total
includes taxes & fees
Apr 26 - Apr 27
Residence Inn Marriott Danbury
Residence Inn Marriott DanburyDanbury
8.2 out of 10, Very Good, (371 reviews)
- Unwind minutes from Danbury Fair Mall with a fitness center and helpful staff.
The price is $133
$153 total
includes taxes & fees
Apr 19 - Apr 20
J House Greenwich
J House GreenwichRiverside
9.0 out of 10, Wonderful, (1,005 reviews)
- Boutique Art Deco retreat with spa indulgences and Italian cuisine by the station.
The price is $242
$320 total
includes taxes & fees
Apr 13 - Apr 14
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHGDanbury
9.2 out of 10, Wonderful, (345 reviews)
- Experience poolside relaxation near popular Danbury attractions and Jumpz Trampoline.
The price is $131
$151 total
includes taxes & fees
Apr 19 - Apr 20
Springhill Suites By Marriott - Danbury
Springhill Suites By Marriott - DanburyDanbury
8.8 out of 10, Excellent, (873 reviews)
The price is $110
$127 total
includes taxes & fees
Apr 19 - Apr 20
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.
Go beyond your typical stay in Ossining
Top landmarks in Ossining
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.
Photo by louann ohora
Open Photo by louann ohora
Check out reviews of Ossining hotels guests love
Hampton Inn White Plains/Tarrytown
10/10 Excellent
