Title: Visit Ossining: 2026 Travel Guide for Ossining, New York | Expedia.com

[Hotels in Ossining](https://expedia.com/Ossining-Hotels.d6190653.Travel-Guide-Hotels)[Vacation Rentals in Ossining](https://expedia.com/Ossining-Vacation-Rentals.d6190653.Travel-Guide-VacationRentals)[Flights to Ossining](https://expedia.com/Cheap-Flights-To-Ossining.d6190653.Travel-Guide-Flights)[Car Rentals in Ossining](https://expedia.com/Car-Rentals-In-Ossining.d6190653.Car-Rental-Guide)[Ossining Vacation Packages](https://expedia.com/Ossining.d6190653.Destination-Travel-Guides)

# Ossining, NY

## Travel Guide

![Boardwalk over marshland on the trail at Teatown Lake Reservation in Ossining, New York.
](https://images.trvl-media.com/place/6190653/d6b06ec0-5d8e-4f01-b77d-2dc521a46ea1.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Westchester, NY, USA: A rail bridge spans an inlet on the Hudson River, with St. Augustine’s Roman Catholic Church, Ossining, NY, in the background. ](https://images.trvl-media.com/place/6190653/472c72dd-f23e-418c-a8d2-105b7dd45c20.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![The start of the Bergmann boardwalk at Teatown Reservation in Westchester County, New York](https://images.trvl-media.com/place/6190653/480e4d5f-1754-4fe2-b689-22410edfde5f.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![rows of Victorian building sit t side by side in downtown Ossining, New York](https://images.trvl-media.com/place/6190653/816a8f53-2df2-4e4a-9d35-0719e8170a31.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Sunset at the Ossining waterfront](https://images.trvl-media.com/place/6190653/9ea2ffd5-f98e-40ce-8c31-b0c6a6a646c1.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

## Visit Ossining

Things to do

- Ossining Hotel Deals
- Vacation Rentals in Ossining

![Windrose On Hudson](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/d1beb6ce_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Windrose On Hudson

1 Shady Lane Farm Road Ossining NY

$181 nightly

$202 total

Apr 1 - Apr 2

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 ...

8.4/10 Very Good! (120 reviews)

hotel grounds are great the rooms need an update the staff is great Margorie is a pleasure to be around the grab and go is great the gym great i did not eat there the restaurant was not open. I would go back even though it is a bit far from my office. they do clean the room every day which to me ...

Reviewed on Mar 20, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F1%2F2026&endDate=4%2F2%2F2026&selected=112806652&PinnedHotelID=112806652&HadPinnedHotel=true&regionId=6190653)

![Baymont by Wyndham White Plains - Elmsford](https://images.trvl-media.com/lodging/1000000/10000/500/438/w8985h6000x10y0-9d556f34_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Baymont by Wyndham White Plains - Elmsford

540 Saw Mill River Rd Elmsford NY

$112 nightly

$128 total

Apr 5 - Apr 6

Total with taxes and fees

Book a stay at this business-friendly hotel in Elmsford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...

8.2/10 Very Good! (1,619 reviews)

Nice hotel, big rooms, basic breakfast, wifi didn’t work properly.

Reviewed on Mar 25, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=438&PinnedHotelID=438&HadPinnedHotel=true&regionId=6190653)

![LIV Hotel Bronx - Newly Built](https://images.trvl-media.com/lodging/118000000/117970000/117967600/117967593/ef0e434d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

LIV Hotel Bronx - Newly Built

3530 Webster Ave Bronx NY

$125 nightly

$147 total

Mar 26 - Mar 27

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.

8.2/10 Very Good! (416 reviews)

First of, the parking is very limited so do not expect that you'll be able to park inside. The person at the reception was not very friendly and it was hard to understand what he was saying. The room was barely clean, we found other people's hair all the time. There was no soap dispenser in the shower, ...

Reviewed on Mar 23, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F26%2F2026&endDate=3%2F27%2F2026&selected=117967593&PinnedHotelID=117967593&HadPinnedHotel=true&regionId=6190653)

[See all 1,351 properties in Ossining](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F26%2F2026&endDate=3%2F27%2F2026&regionId=6190653)

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!](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/05588dfc_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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 Nelson Park and Sing Sing Prison Museum are located ...

9.2/10 Wonderful! (7 reviews)

Super fun location! Host was very helpful. The house is very comfortable for large groups

Reviewed on Dec 1, 2025

[](https://expedia.com/Ossining-Hotels-Castle-Retreat-W-Pool.h101852343.Hotel-Information)

![Stamford Suites](https://images.trvl-media.com/lodging/1000000/30000/25900/25900/b7db331c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Stamford Suites

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. ...

[](https://expedia.com/Stamford-Hotels-Stamford-Suites.h25900.Hotel-Information)

![Global Luxury Suites White Plains](https://images.trvl-media.com/lodging/75000000/74130000/74125800/74125740/343ab6e5_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Global Luxury Suites White Plains

57 Bank St White Plains NY

Book a stay at this business-friendly apartment in White Plains. Enjoy free WiFi, an outdoor pool, and valet parking (surcharge). Popular attractions Westchester ...

6.8/10 (42 reviews)

Stayed for 5 nights. The air filter was absolutely polluted with dust, it looked like it hasn’t been changed in a year. Our son got an allergic reaction to the dust and had to take him to the ER during our stay. One of the beds did not have a comforter which we reported upon arrival. We were told ...

Reviewed on Mar 17, 2026

[](https://expedia.com/White-Plains-Hotels-Global-Luxury-Suites-White-Plains.h74125740.Hotel-Information)

[See all properties in Ossining](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&regionId=6190653&sort=VACATION_RENTAL)

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.

## Check Ossining hotel availability

[Tonight

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6190653&startDate=2026-03-25&endDate=2026-03-26)[Mar 25 - Mar 26](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6190653&startDate=2026-03-25&endDate=2026-03-26)

[Tomorrow night

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6190653&startDate=2026-03-26&endDate=2026-03-27)[Mar 26 - Mar 27](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6190653&startDate=2026-03-26&endDate=2026-03-27)

[This weekend

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6190653&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026)[Mar 27 - Mar 29](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6190653&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026)

[Next weekend

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6190653&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026)[Apr 3 - Apr 5](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6190653&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026)

### Popular places to visit

![Rest stop area beside interstate highway where travelers rest and sight see Tioga Reservoir and Dam in Pennsylvania New York state border](https://images.trvl-media.com/place/835647549279940608/a2b5cdb4-0d08-4c9d-b8b4-e47aa8caa5da.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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. 

[](https://expedia.com/Travelers-Rest-Ossining.d835647549279940608.Vacation-Attraction)

![Lovely spot in Westchester, NY](https://images.trvl-media.com/place/553248621560458588/f1c654af-0d4d-4605-9da4-0e6de2024125.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Teatown Lake Reservation

Explore the great outdoors at Teatown Lake Reservation, a lovely green space in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants. 

[](https://expedia.com/Teatown-Lake-Reservation-Ossining.d553248621560458588.Vacation-Attraction)

#### Sing Sing Correctional Facility

After visiting Sing Sing Correctional Facility, make a plan to see the other sights and activities in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants. 

[](https://expedia.com/Sing-Sing-Correctional-Facility-Ossining.d553248621558038857.Vacation-Attraction)

#### Thomas J. Watson Research Center

Learn about the local history of Ossining with a stop at Thomas J. Watson Research Center. Stroll along the riverfront in this quaint area, or check out its top-notch restaurants. 

[](https://expedia.com/Thomas-J-Watson-Research-Center-Ossining.d6087173.Vacation-Attraction)

#### Sing Sing Prison Museum

You can spend time browsing the exhibits at Sing Sing Prison Museum during your travels in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants. 

[](https://expedia.com/Sing-Sing-Prison-Museum-Ossining.d553248621561873062.Vacation-Attraction)

#### Depot Square

Explore the great outdoors at Depot Square, a lovely green space in Ossining. Stroll along the riverfront or attend a sporting event in this family-friendly area. 

[](https://expedia.com/Depot-Square-Ossining.d553248621558038859.Vacation-Attraction)

## Cities near Ossining

![Stone bridge in Rockefeller State Park over the Pocantico River in autumn](https://images.trvl-media.com/place/7040/56c49846-1e91-46dc-9c8b-5e16bbfa762f.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Briarcliff Manor

![Mount Kisco Train Station, Westchester, New York, snow, ](https://images.trvl-media.com/place/8984/0ed5affd-7834-4854-bad9-59a4774033d3.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Mount Kisco

![New Croton Dam, Croton-On-Hudson, Croton Gorge Park, NY. USA](https://images.trvl-media.com/place/183658/bacd69ec-8a6e-411e-9107-e3c7591a0652.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Croton-on-Hudson

![Late afternoon aerial autumn image of the area surrounding the Yorktown Heights, NY, USA  10-16-2024](https://images.trvl-media.com/place/6338662/af34e37e-44d4-4788-b8d3-d7dabc7141b3.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Yorktown Heights

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- [Sing Sing Prison Museum ](https://www.expedia.com/Sing-Sing-Prison-Museum-Ossining.d553248621561873062.Vacation-Attraction)
- [Snowden Avenue Park ](https://www.expedia.com/Snowden-Avenue-Park-Ossining.d553248621558038861.Vacation-Attraction)
- [Depot Square ](https://www.expedia.com/Depot-Square-Ossining.d553248621558038859.Vacation-Attraction)
- [Sing Sing Correctional Facility ](https://www.expedia.com/Sing-Sing-Correctional-Facility-Ossining.d553248621558038857.Vacation-Attraction)
- [Nelson Park ](https://www.expedia.com/Nelson-Park-Ossining.d553248621557931331.Vacation-Attraction)
- [Louis Engel Waterfront Park ](https://www.expedia.com/Louis-Engel-Waterfront-Park-Ossining.d553248621587293691.Vacation-Attraction)
- [Visit Maryknoll ](https://www.expedia.com/Maryknoll.dx3000449058)
- [Visit Briarcliff Manor ](https://www.expedia.com/Briarcliff-Manor.dx7040)
- [Croton Point Park ](https://www.expedia.com/Croton-Point-Park-Croton-on-Hudson.d6093731.Vacation-Attraction)
- [Van Cortlandt Manor ](https://www.expedia.com/Van-Cortlandt-Manor-Croton-on-Hudson.d6207691.Vacation-Attraction)
- [Corning Tower ](https://www.expedia.com/Corning-Tower-Croton-on-Hudson.d553248621532664094.Vacation-Attraction)
- [Visit Croton-on-Hudson ](https://www.expedia.com/Croton-On-Hudson.dx183658)
- [Hardscrabble Wilderness Area ](https://www.expedia.com/Hardscrabble-Wilderness-Area-Briarcliff-Manor.d553248621587293678.Vacation-Attraction)
- [Rockland Lake State Park Championship Golf Course ](https://www.expedia.com/Rockland-Lake-State-Park-Championship-Golf-Course-Congers.d6253469.Vacation-Attraction)
- [Visit Millwood ](https://www.expedia.com/Millwood.dx3000449093)
- [Croton Landing Park ](https://www.expedia.com/Croton-Landing-Park-Croton-on-Hudson.d553248621587293679.Vacation-Attraction)
- [Where to stay in Croton-on-Hudson ](https://www.expedia.com/Croton-On-Hudson.dx183658.Where-To-Stay)

- [Car rentals near Ossining Historical Society ](https://www.expedia.com/Car-Rentals-In-Ossining-Historical-Society.d6207717.Car-Rental-Guide)
- [Car rentals near Crotonville ](https://www.expedia.com/Car-Rentals-In-Crotonville.d553248635975868892.Car-Rental-Guide)
- [Car rentals near Briarcliff Manor ](https://www.expedia.com/Car-Rentals-In-Briarcliff-Manor.d7040.Car-Rental-Guide)
- [Avis Rental Cars in Briarcliff Manor ](https://www.expedia.com/Avis-Car-Rentals-In-Briarcliff-Manor.d7040-c41.Car-Rental-Guide-Suppliers)
- [Mini Car Rentals in Briarcliff Manor ](https://www.expedia.com/Mini-Car-Rentals-In-Briarcliff-Manor.d7040-tMini.Car-Rental-Guide-Class)
- [Car rentals near Van Cortlandt Manor ](https://www.expedia.com/Car-Rentals-In-Van-Cortlandt-Manor.d6207691.Car-Rental-Guide)
- [Car rentals near Croton Point Park ](https://www.expedia.com/Car-Rentals-In-Croton-Point-Park.d6093731.Car-Rental-Guide)
- [Car rentals near Hudson Hills Golf Course ](https://www.expedia.com/Car-Rentals-In-Hudson-Hills-Golf-Course.d553248621532664565.Car-Rental-Guide)
- [Car rentals near Croton-on-Hudson ](https://www.expedia.com/Car-Rentals-In-Croton-On-Hudson.d183658.Car-Rental-Guide)
- [Enterprise Rental Cars in Croton-on-Hudson ](https://www.expedia.com/Enterprise-Car-Rentals-In-Croton-On-Hudson.d183658-c15.Car-Rental-Guide-Suppliers)
- [Hertz Rental Cars in Croton-on-Hudson ](https://www.expedia.com/Hertz-Car-Rentals-In-Croton-On-Hudson.d183658-c40.Car-Rental-Guide-Suppliers)
- [Dollar Rent A Car Rental Cars in Croton-on-Hudson ](https://www.expedia.com/Dollar-Rent-A-Car-Car-Rentals-In-Croton-On-Hudson.d183658-c43.Car-Rental-Guide-Suppliers)
- [Alamo Rent A Car Rental Cars in Croton-on-Hudson ](https://www.expedia.com/Alamo-Rent-A-Car-Car-Rentals-In-Croton-On-Hudson.d183658-c6.Car-Rental-Guide-Suppliers)
- [Van Car Rentals in Croton-on-Hudson ](https://www.expedia.com/Van-Car-Rentals-In-Croton-On-Hudson.d183658-tVan.Car-Rental-Guide-Class)

- [Croton-On-Hudson Vacation Rentals ](https://www.expedia.com/Croton-On-Hudson-Vacation-Rentals.d183658.Travel-Guide-VacationRentals)

- [Things to do in Maryknoll ](https://www.expedia.com/Things-To-Do-In-Maryknoll.d3000449058.Travel-Guide-Activities)
- [Things to do in Briarcliff Manor ](https://www.expedia.com/Things-To-Do-In-Briarcliff-Manor.d7040.Travel-Guide-Activities)

- Cities near Ossining
- Places of interest

[Briarcliff Manor](https://expedia.com/Briarcliff-Manor.dx7040)[Mount Kisco](https://expedia.com/Mount-Kisco.dx8984)[Chappaqua](https://expedia.com/Chappaqua.dx88470)[Croton-on-Hudson](https://expedia.com/Croton-On-Hudson.dx183658)[Yorktown Heights](https://expedia.com/Yorktown-Heights.dx6338662)[Maryknoll](https://expedia.com/Maryknoll.dx3000449058)[Millwood](https://expedia.com/Millwood.dx3000449093)

- [Sing Sing Correctional Facility ](https://expedia.com/Sing-Sing-Correctional-Facility-Ossining.d553248621558038857.Vacation-Attraction)
- [Thomas J. Watson Research Center ](https://expedia.com/Thomas-J-Watson-Research-Center-Ossining.d6087173.Vacation-Attraction)
- [Teatown Lake Reservation ](https://expedia.com/Teatown-Lake-Reservation-Ossining.d553248621560458588.Vacation-Attraction)
- [Nelson Park ](https://expedia.com/Nelson-Park-Ossining.d553248621557931331.Vacation-Attraction)
- [Sing Sing Prison Museum ](https://expedia.com/Sing-Sing-Prison-Museum-Ossining.d553248621561873062.Vacation-Attraction)
- [Depot Square ](https://expedia.com/Depot-Square-Ossining.d553248621558038859.Vacation-Attraction)
- [Louis Engel Waterfront Park ](https://expedia.com/Louis-Engel-Waterfront-Park-Ossining.d553248621587293691.Vacation-Attraction)
- [Ossining Historical Society ](https://expedia.com/Ossining-Historical-Society-Ossining.d6207717.Vacation-Attraction)
- [Kitchawan Preserve ](https://expedia.com/Kitchawan-Preserve-Ossining.d553248621560458590.Vacation-Attraction)
- [Snowden Avenue Park ](https://expedia.com/Snowden-Avenue-Park-Ossining.d553248621558038861.Vacation-Attraction)
- [Hudson Hills Golf Course ](https://expedia.com/Hudson-Hills-Golf-Course-Ossining.d553248621532664565.Vacation-Attraction)
- [Woodbury Common Premium Outlets ](https://expedia.com/Woodbury-Common-Premium-Outlets-Central-Valley.d6127054.Vacation-Attraction)
- [Westchester County Center ](https://expedia.com/Westchester-County-Center-White-Plains.d6066133.Vacation-Attraction)
- [NewYork-Presbyterian - Westchester Hospital ](https://expedia.com/NewYork-Presbyterian-Westchester-Hospital-Bronxville.d553248621591002858.Vacation-Attraction)
- [United States Military Academy ](https://expedia.com/United-States-Military-Academy-New-York.d6093733.Vacation-Attraction)
- [Bear Mountain State Park ](https://expedia.com/Bear-Mountain-State-Park-New-York.d6127050.Vacation-Attraction)
- [Empire City Casino ](https://expedia.com/Empire-City-Casino-Southeast-Yonkers.d6172190.Vacation-Attraction)
- [New Roc City ](https://expedia.com/New-Roc-City-Downtown-Rochelle.d6179751.Vacation-Attraction)
- [Sarah Lawrence College ](https://expedia.com/Sarah-Lawrence-College-Bronxville.d6087163.Vacation-Attraction)
- [Westchester's Ridge Hill ](https://expedia.com/Westchesters-Ridge-Hill-Northeast-Yonkers.d553248621558114293.Vacation-Attraction)
- [Tarrytown Music Hall ](https://expedia.com/Tarrytown-Music-Hall-Downtown-Tarrytown.d6211022.Vacation-Attraction)
- [Capitol Theatre ](https://expedia.com/Capitol-Theatre-Rye-Brook.d553248621532664534.Vacation-Attraction)
- [Greenwich Avenue ](https://expedia.com/Greenwich-Avenue-Downtown-Greenwich.d6207662.Vacation-Attraction)
- [Hudson River ](https://expedia.com/Hudson-River-New-York.d681942362185793536.Vacation-Attraction)
- [Lyndhurst Mansion ](https://expedia.com/Lyndhurst-Mansion-Tarrytown.d6093725.Vacation-Attraction)
- [Paramus Park Mall ](https://expedia.com/Paramus-Park-Mall-Paramus.d6079833.Vacation-Attraction)

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