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

This weekend
Jun 5 - Jun 7
Next weekend
Jun 12 - Jun 14

Where to stay in Ossining?

Restaurant

Windrose On Hudson

Windrose On Hudson
3.0 star property
Ossining
8.4 out of 10, Very Good, (158 reviews)
Unwind at this Hudson River retreat with serene views. The cozy café offers breakfast while the fitness center keeps your routine intact. Near Van Cortlandt Manor and Croton Point Park, this hotel provides free WiFi and parking for easy Westchester exploration.
The price is $206
$230 total
includes taxes & fees
Jun 21 - Jun 22
Windrose On Hudson
House (5 Bedrooms) | Interior

Ossining Vacation Rental Near River, Trails & Mta!

Ossining Vacation Rental Near River, Trails & Mta!
3.0 star property
Ossining
Escape to this waterfront gem in Ossining with its own marina, where patios offer peaceful garden views. The fully-equipped kitchen and DVD player make family stays comfortable, while nearby historical society and parks await exploration.
The price is $306
$882 total
includes taxes & fees
Jun 14 - Jun 15
Ossining Vacation Rental Near River, Trails & Mta!
House, Smoking | 5 bedrooms

Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is $1,084
$1,673 total
includes taxes & fees
Jun 23 - Jun 24
Summer Pool Oasis Custom Bar Arcade Pool Table
Lobby

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.2 out of 10, Very Good, (49 reviews)
The price is $95
$117 total
includes taxes & fees
Jun 9 - Jun 10
Comfort Suites Central Valley - Woodbury
Lobby sitting area

Heidi's Inn

Heidi's Inn
2.5 star property
Brewster
8.8 out of 10, Excellent, (841 reviews)
This charming inn near Brewster Train Station offers free breakfast, WiFi, and parking. Enjoy the seasonal pool after hiking nearby trails. Rooms include refrigerators and microwaves, plus a peaceful garden and terrace to unwind.
The price is $148
$160 total
includes taxes & fees
Jun 2 - Jun 3
Heidi's Inn
Exterior

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG
2.5 star property
Danbury
9.2 out of 10, Wonderful, (374 reviews)
This business-friendly hotel offers an outdoor pool and fitness center just minutes from Jumpz Trampoline and Thrillz Adventure Park. Enjoy clean rooms with free WiFi, plus complimentary breakfast to start your day. The helpful staff ensures a comfortable stay.
The price is $139
$160 total
includes taxes & fees
Jun 7 - Jun 8
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG
Business center

Americas Best Value Inn at Central Valley-Woodbury

Americas Best Value Inn at Central Valley-Woodbury
2.0 star property
Central Valley
7.2 out of 10, Good, (1,003 reviews)
Central Valley motel just 15 minutes from Woodbury Common Premium Outlets and LEGOLAND New York. Guests praise the helpful staff, clean rooms, and overall value. Enjoy complimentary WiFi and parking, plus easy access to Bear Mountain State Park and Old Glory Mall.
The price is $100
$123 total
includes taxes & fees
Jun 2 - Jun 3
Americas Best Value Inn at Central Valley-Woodbury
Restaurant

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1,009 reviews)
This historic hotel offers deep-tissue massages at the spa and refreshments at the bar. Just 15 minutes from Bear Mountain State Park with nearby shopping outlets, rooms include microwaves and fridges for added convenience.
The price is $169
$208 total
includes taxes & fees
Jun 2 - Jun 3
Overlook Lodge at Bear Mountain
Lobby

LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built
3.0 star property
Bronx
8.2 out of 10, Very Good, (599 reviews)
Modern rooms in the heart of the Bronx, with Yankee Stadium and Bronx Zoo within a 10-minute drive. Free WiFi and parking add value, while proximity to Gun Hill Rd. Station and Norwood Station connects you to Manhattan attractions like Columbia University and Central Park.
The price is $125
$147 total
includes taxes & fees
Jun 2 - Jun 3
LIV Hotel Bronx - Newly Built
Reception

Dream Hotel Bronx

Dream Hotel Bronx
2.0 star property
South Side
7.2 out of 10, Good, (94 reviews)
The price is $134
$149 total
includes taxes & fees
Jun 2 - Jun 3
Dream Hotel Bronx
Lobby

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,116 reviews)
Wake up to a complimentary breakfast at this convenient hotel near shopping destinations. The indoor pool offers year-round relaxation after exploring nearby attractions. Rooms include refrigerators and microwaves, with free WiFi and parking completing your comfortable stay.
The price is $122
$150 total
includes taxes & fees
Jun 8 - Jun 9
Hampton Inn Harriman Woodbury
Lobby sitting area

The Thayer Hotel at West Point

The Thayer Hotel at West Point
3.5 star property
West Point
9.0 out of 10, Wonderful, (728 reviews)
Perched along the Hudson River, this stately hotel combines military tradition with modern comfort. Explore Bear Mountain State Park and West Point Museum nearby. The attentive staff delivers exceptional service in this well-maintained riverside retreat.
The price is $194
$256 total
includes taxes & fees
Jun 30 - Jul 1
The Thayer Hotel at West Point
Lobby

Best Western The Inn at Ramsey-Mahwah

Best Western The Inn at Ramsey-Mahwah
3.0 star property
Ramsey
7.2 out of 10, Good, (1,005 reviews)
Escape to this welcoming retreat just 9 minutes from Ramsey Route 17 Station. Enjoy complimentary breakfast, WiFi and parking while exploring nearby Campgaw Mountain Ski Area. Guests consistently praise the helpful staff and morning meal.
The price is $120
$138 total
includes taxes & fees
Jun 2 - Jun 3
Best Western The Inn at Ramsey-Mahwah
Lobby

Comfort Inn Brewster

Comfort Inn Brewster
2.5 star property
Brewster
8.8 out of 10, Excellent, (569 reviews)
Unwind at this convenient Brewster hotel offering complimentary daily buffet breakfast and self parking. Just minutes from Old Salem Farm, the fitness center keeps your routine on track while friendly staff ensure a pleasant stay in clean, well-appointed rooms.
The price is $144
$156 total
includes taxes & fees
Jun 28 - Jun 29
Comfort Inn Brewster
Dinner served

Ethan Allen Hotel

Ethan Allen Hotel
3.5 star property
Danbury
8.0 out of 10, Very Good, (1,227 reviews)
Convenient to a train station, this hotel offers free WiFi and parking. Splash around in the seasonal outdoor pool, grab a drink at the bar, or exercise in the fitness center. Clean rooms with comfy beds await after exploring nearby Xtreme Play Adventure Park.
The price is $116
$134 total
includes taxes & fees
Jun 7 - Jun 8
Ethan Allen Hotel
Exterior

Holiday Inn Express Ramsey-Mahwah by IHG

Holiday Inn Express Ramsey-Mahwah by IHG
2.5 star property
Ramsey
9.2 out of 10, Wonderful, (1,001 reviews)
Surprisingly peaceful stay awaits at this business-friendly hotel in Ramsey. Enjoy the 24-hour fitness center, free daily buffet breakfast, and complimentary WiFi and parking. The helpful staff ensures comfort while you explore nearby Tice's Corner attractions.
The price is $135
$155 total
includes taxes & fees
Jun 8 - Jun 9
Holiday Inn Express Ramsey-Mahwah by IHG
Interior entrance

Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
3.0 star property
Mount Kisco
8.6 out of 10, Excellent, (1,002 reviews)
Splash into the seasonal outdoor pool after a day of exploring attractions like Grand Prix New York. This quiet retreat offers dinner at The Hub restaurant, bar service, and helpful staff ready to enhance your stay near Westchester County.
The price is $155
$177 total
includes taxes & fees
Jun 29 - Jun 30
Hotel MTK Mount Kisco
Terrace/patio

Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury
4.0 star property
Danbury
9.2 out of 10, Wonderful, (1,003 reviews)
Set in Danbury, this hotel offers Italian cuisine at Terra restaurant and a stylish bar/lounge. Near Thrillz High Flying Adventure Park, it provides free WiFi, parking, and room service. Travelers appreciate the attentive staff and convenient access to local attractions.
The price is $171
$196 total
includes taxes & fees
Jun 30 - Jul 1
Hotel Zero Degrees Danbury
Towels

Garner Hotel Mahwah by IHG

Garner Hotel Mahwah by IHG
2.5 star property
Mahwah
9.0 out of 10, Wonderful, (460 reviews)
This business-friendly hotel offers clean rooms and exceptional staff service. Located within walking distance of Mahwah Station and a short drive from Suffern Railroad Museum. Continental breakfast is served daily, with free WiFi and parking included.
The price is $115
$132 total
includes taxes & fees
Jun 7 - Jun 8
Garner Hotel Mahwah by IHG
Aerial view

West Point Motel

West Point Motel
2.5 star property
Highland Falls
8.6 out of 10, Excellent, (701 reviews)
Enjoy a convenient stay near Bear Mountain State Park at this Highland Falls motel. Clean rooms feature rainfall showerheads and satellite TV. West Point Museum is nearby, and LaGuardia Airport is 75 minutes away by car.
The price is $120
$148 total
includes taxes & fees
Jun 14 - Jun 15
West Point Motel
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.
View all properties

When is the best time to visit Ossining?

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
View properties in June
Currently viewing crowd sizes and weather for June.
Typical weather for Ossining
June
High 26°C / low 16°C. Sunny most days.
View properties in June
26°
weather_sun
June, no crowd data, average high temperature 26 degrees Celsius, average low temperature 16 degrees Celsius. Sunny most days.
16°
29°
weather_sun
July, no crowd data, average high temperature 29 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
20°
28°
weather_sun
August, no crowd data, average high temperature 28 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
19°
24°
weather_sun
September, no crowd data, average high temperature 24 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
18°
weather_sun
October, no crowd data, average high temperature 18 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
10°
11°
weather_sun
November, no crowd data, average high temperature 11 degrees Celsius, average low temperature 3 degrees Celsius. Sunny most days.
3°
5°
weather_partly_sunny
December, no crowd data, average high temperature 5 degrees Celsius, average low temperature 0 degrees Celsius. Partly sunny.
0°
2°
ac_unit
January, no crowd data, average high temperature 2 degrees Celsius, average low temperature -4 degrees Celsius. Snow likely.
-4°
4°
ac_unit
February, no crowd data, average high temperature 4 degrees Celsius, average low temperature -4 degrees Celsius. Snow likely.
-4°
8°
weather_partly_sunny
March, no crowd data, average high temperature 8 degrees Celsius, average low temperature 0 degrees Celsius. Partly sunny.
0°
15°
weather_sun
April, no crowd data, average high temperature 15 degrees Celsius, average low temperature 6 degrees Celsius. Sunny most days.
6°
21°
weather_sun
May, no crowd data, average high temperature 21 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
11°
Monthly weather averages (˚C)

Top landmarks in Ossining

Rest stop area beside interstate highway where travelers rest and sight see Tioga Reservoir and Dam in Pennsylvania New York state border

Travelers Rest

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

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
Open Photo by louann ohora

Check out reviews of Ossining hotels guests love

Amsterdam Hotel

Amsterdam Hotel

6/10 Okay
"Breakfast was Terrible"
Jason 2-night trip
Posted 2 hours ago
Amsterdam Hotel

Frequently asked questions

What accommodations do travelers recommend in Ossining?
Guests like Windrose On Hudson, Armoni Inn & Suites and Baymont by Wyndham White Plains - Elmsford.
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.