A wooden bridge over a lake with a sign reading "BERGMANN BOARDWALK".

Hotels in Ossining

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A spacious indoor area with large windows, modern furniture, and a view of a landscaped outdoor area.

A hotel lobby with a reception desk, a seating area with a table, and potted plants.

A hotel lobby with a large digital map display, comfortable seating areas, and a reception desk.

A cafe with brick walls, a wooden counter, and a window with natural light.

1. Windrose On Hudson

Ossining

$156

$174 total

includes taxes & fees

Nov 8 - Nov 9

A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

A swimming pool with lounge chairs and a wooden deck, surrounded by trees and a building with a sloped roof.

A traditional Tudor-style house with a spacious front yard, a stone wall, and a well-maintained garden.

A modern living room with a sectional sofa, a coffee table, and large windows offering a view of trees.

2. Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

$462

$988 total

includes taxes & fees

Nov 4 - Nov 5

A modern bar area with a bar counter, multiple stools, and a seating area with a sofa and chairs.

A modern dining area with a wooden table, cushioned seating, pendant lighting, and a large window offering a view of the outdoors.

A modern lounge with leather sofas, a patterned rug, and red pendant lights.

A modern building with a glass facade, a red door, and a staircase leading to the entrance.

3. Hotel Nyack, a JdV by Hyatt Hotel

Nyack

$106

$148 total

includes taxes & fees

Nov 22 - Nov 23

A modern reception area with a wooden reception desk, a blue accent wall, and a large glass door leading to an outdoor seating area.

A hotel room with two beds, a blue sofa, a wooden coffee table, and a painting on the wall.

A Holiday Inn Express & Suites hotel with a modern design, featuring a covered entrance and American flags.

An indoor swimming pool with a tiled floor, a ceiling with a grid pattern, and a view of greenery outside.

4. Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Hawthorne

$138

$158 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with a central island, bar stools, a fireplace, and a contemporary pendant light.

A modern interior with a dark wall, a wooden reception desk, a refrigerator stocked with beverages, shelves with snacks, and a large vase with orange flowers.

A modern cafe with multiple seating options including tables, chairs, and sofas.

A modern hotel lobby with a large digital display on the wall, a reception desk, a comfortable seating area with a sofa and cushions, and a clean, tiled floor.

5. Courtyard by Marriott Tarrytown Westchester County

Tarrytown

$152

$174 total

includes taxes & fees

Nov 1 - Nov 2

A modern hotel lobby with a kitchen area, seating arrangements, and large windows offering a view of the outdoors.

A hotel room with a large bed, a desk, and a chair. There is a window with curtains and a wall with a geometric patterned design.

An indoor swimming pool with a glass ceiling, clear signage indicating depth, and lounge chairs along the sides.

A hotel corridor with a patterned carpet, a railing, and a reception desk with a glass partition.

6. Baymont by Wyndham White Plains - Elmsford

Elmsford

$135

$155 total

includes taxes & fees

Nov 15 - Nov 16

A spacious lobby with a red sofa, green armchairs, a fireplace, and a staircase leading to an upper level.

An outdoor patio area with tables and chairs, red umbrellas, and flower planters.

A spacious restaurant with high tables and stools, a bar area, and a television screen displaying a sports game.

A spacious lobby with a red sofa set, a fireplace, and a staircase leading to an upper level.

7. Hotel MTK Mount Kisco

Mount Kisco

$134

$154 total

includes taxes & fees

Nov 9 - Nov 10

A spacious lobby with a reception desk, sofas, and a coffee table. There are multiple seating areas and a large window providing natural light.

An indoor swimming pool with a 3 feet 10 inches deep sign, surrounded by a white tiled area, benches, and a glass door leading to another room.

A gym with exercise equipment, large windows, and a wooden reception desk.

A Sheraton hotel with a modern facade, multiple floors, and a prominent entrance.

8. Sheraton Tarrytown Hotel

Tarrytown

$135

$155 total

includes taxes & fees

Nov 22 - Nov 23

A checkered floor, a potted plant, and two metal ladders in a room with large windows.

A modern building with a glass facade, surrounded by a landscaped garden with various plants and a classical-style urn.

A modern office space with a large desk, multiple printers, and comfortable seating.

A restaurant with a counter, stools, and a menu board.

9. West Gate Inn Nyack

Nyack

$110

$126 total

includes taxes & fees

Nov 8 - Nov 9

A hotel with a modern facade, a prominent signage for SpringHill Suites Marriott, and a covered entrance area with seating.

A bar area with a long counter, multiple chairs, and a television mounted on the wall.

A modern living room with two orange patterned armchairs, a glass coffee table, a flat-screen TV mounted above a fireplace, and a magazine on the table.

A buffet setup with various food items, a coffee station, and seating area.

10. SpringHill Suites by Marriott Tarrytown Westchester County

Tarrytown

$156

$178 total

includes taxes & fees

Nov 1 - Nov 2

A spacious room with a stone fireplace, white sofas, and a large window offering a view of the outdoors.

An outdoor patio with tables and chairs, surrounded by large umbrellas.

A spacious corridor with stone walls, large windows, and a central chandelier.

A modern building with a stone facade and wooden beams, surrounded by a well-maintained lawn and trees.

11. Sleepy Hollow Hotel, a Dolce by Wyndham

Tarrytown

$143

$164 total

includes taxes & fees

Nov 1 - Nov 2

A historic stone building with a turret, arched entrance, and a covered patio area.

A large building with a white facade and columns, surrounded by a lawn with outdoor seating and string lights.

A spacious lobby with a high ceiling, patterned walls, and a central seating area with ottomans and a coffee table.

A spacious lobby with a staircase, seating area, and large windows offering a view of the outdoors.

12. Tarrytown House Estate

Tarrytown

$159

$206 total

includes taxes & fees

Nov 24 - Nov 25

An outdoor seating area with wicker chairs and tables, surrounded by greenery and a modern lamp structure.

A bar area with a long counter, multiple shelves with bottles, and several bar stools.

A modern lobby with a reception desk, seating area, and a kitchen in the background.

A formal dining setup with multiple tables, each set with clear glassware, plates, and cutlery.

13. Westchester Marriott

Tarrytown

$179

$205 total

includes taxes & fees

Nov 22 - Nov 23

A Holiday Inn Express & Suites sign with a bench and flower beds in front.

A coffee station with two coffee machines and a variety of coffee pods and cups.

A hotel room with a patterned sofa, a small ottoman, a desk with two chairs, a microwave, a wine bottle, and a framed picture on the wall.

A hotel room with a sofa, a coffee table, a TV, a desk, and a bed.

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

Peekskill

$131

$150 total

includes taxes & fees

Nov 22 - Nov 23

A restaurant with a bar area, multiple seating options including booths and tables, and a television screen mounted on the wall.

A spacious lobby with a modern design, featuring a seating area with sofas and armchairs, a decorative wall panel, and a large window providing natural light.

A modern building with large glass windows, a brick facade, and a curved section.

15. DoubleTree by Hilton Hotel Nanuet

Nanuet

$127

$147 total

includes taxes & fees

Nov 22 - Nov 23

A modern kitchen with a large island, bar stools, a flat-screen TV, and a stone backsplash.

A lobby with teal patterned chairs, a fireplace, and a flat-screen TV mounted above it.

A hotel room with a bed, a sofa, a nightstand, a lamp, and a framed picture on the wall.

A snack and beverage vending area with a refrigerator and shelves stocked with various snacks and drinks.

16. Hampton Inn White Plains/Tarrytown

Elmsford

$113

$129 total

includes taxes & fees

Nov 22 - Nov 23

A snow-covered outdoor area with a stone wall, a metal fence, and a lamp post.

A hotel room with two beds, a large window with curtains, a door, and a small table with a lamp.

A view from a window overlooking a lake with trees and hills in the distance.

A view from a covered porch overlooking a lake, with a white fence and trees in the foreground.

17. Inn on the Hudson

Peekskill

$104

$119 total

includes taxes & fees

Nov 1 - Nov 2

A spacious hotel lobby with a modern design, featuring a large seating area, a dining table, and large windows providing views of the outdoors.

A large indoor swimming pool with clear glass walls, multiple lounge chairs, and ceiling lights.

An outdoor patio with stone walls, a fire pit, and seating.

A modern kitchen with a central island, bar stools, wooden cabinets, and pendant lighting.

18. Element by Marriott Spring Valley

Spring Valley

$134

$156 total

includes taxes & fees

Nov 22 - Nov 23

A breakfast area with multiple tables and chairs, a kitchen area with appliances, and a sign for Daybreak Breakfast.

A Days Inn lobby with a stone accent wall, a reception desk, and a sign indicating check-in times.

A Days Inn with a brick facade, a covered walkway, and a parking lot.

A hotel room with a bed, a desk, and a chair. There are two framed pictures on the wall.

19. Days Inn by Wyndham Elmsford / White Plains

Elmsford

$119

$136 total

includes taxes & fees

Nov 1 - Nov 2

A spacious lobby with a central reception desk, two large potted plants, and a patterned rug.

A Hilton Garden Inn with a clear sky, a covered entrance, and multiple flags.

A modern hotel lobby with a fireplace, seating area, and a bar cart with bottles.

A bar area with a white countertop, bar stools, a television, and various bottles.

20. Hilton Garden Inn Nanuet

Nanuet

$118

$137 total

includes taxes & fees

Nov 1 - Nov 2

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Go beyond your typical stay in Ossining

Our prices for hotels in Ossining are cheapest in December

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 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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Louis Engel Waterfront Park

Louis Engel Waterfront Park is worth a visit, located 0.8 mi (1.3 km) from central Ossining. Why not take a stroll along the riverfront and watch the sunset while you're here?

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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 Historical Society

Ossining Historical Society is 0.9 mi (1.4 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? If you want to experience more of the culture Ossining has to offer, head to Van Cortlandt Manor, Croton Point Park, and Rockefeller State Park Preserve.

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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.

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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.

See all hotels in Ossining

Check out reviews of Ossining hotels guests love

Windrose On Hudson

Ossining

10/10 Exceptional

Nickie

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Hawthorne

10/10 Exceptional

Lorena

Hotel Nyack, a JdV by Hyatt Hotel

Nyack

10/10 Exceptional

JASON

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

Peekskill

10/10 Exceptional

David Allen

Courtyard by Marriott Tarrytown Westchester County

Tarrytown

10/10 Exceptional

Stephen

SpringHill Suites by Marriott Tarrytown Westchester County

Tarrytown

10/10 Exceptional

James

DoubleTree by Hilton Hotel Nanuet

Nanuet

10/10 Exceptional

Brenda

Westchester Marriott

Tarrytown

10/10 Exceptional

This hotel was nice, the only thing I was not a big fan of was the overcrowded lobby. I felt like it was a hassle to enter and exit the doors because people were permitted to block doorways and the main hallway to get to the elevators. I understand people are eager to congregate, but a kind reminder to move over for guests just trying to get up to their rooms by staff would have made the experience much more welcoming.

KELLY

Hotel MTK Mount Kisco

Mount Kisco

10/10 Exceptional

Overall our stay at MTK was very positive. Generally staff was responsive and friendly but not our experience in the restaurant. Service person barely greeted us, sat looking at his phone, apparently not checking on our food for which we waited a very long time. He made it quite clear that he did not enjoy his job and did not want to be there. However, we definitely would stay at MTK again without hesitation.

Shirley

Tarrytown House Estate

Tarrytown

10/10 Exceptional

James

Baymont by Wyndham White Plains - Elmsford

Elmsford

10/10 Exceptional

Norma Jean

Sheraton Tarrytown Hotel

Tarrytown

10/10 Exceptional

Jason

A stone building with a tower, surrounded by a garden with large rocks and various plants.

A stone fire pit with flames, surrounded by benches and a building with large windows in the background.

A dining area with large windows, wooden tables, and chairs.

A hotel room with two beds, a dining area with a table and chairs, a TV mounted on the wall, and a large window with a view of trees.

The Abbey Inn & Spa

Peekskill

10/10 Exceptional

Ralph

A modern lobby with seating areas, a fireplace, and a flat-screen TV mounted on the wall.

A modern hotel lobby with a large sofa, dining area, and large windows offering city views.

A spacious hotel lobby with a modern design, featuring a central seating area with sofas and armchairs, a coffee table, and a television.

A modern lobby with a reception desk, seating area, and a decorative wall.

Cambria Hotel & Suites - White Plains Downtown

White Plains

10/10 Exceptional

Keeping in mind its 3-star classification, this hotel does not disappoint. Front desk staff is outstanding. Metro-North station is in easy walking distance. Of special note: In partnership with the Chazz Palminteri restaurant next door, guests can order a meal, get it delivered and charged to the room. Very nice option when traveling all day. On a lesser note, the slamming doors made a lot of disruption. Soft close, as in other hotels, would improve the guest experience and be worth the...

William

Element by Marriott Spring Valley

Spring Valley

10/10 Exceptional

Jasmine

An outdoor seating area with modern furniture, a fire pit, and ambient lighting.

An indoor swimming pool with clear water, surrounded by lounge chairs and a seating area.

A modern lobby with a large, tufted sofa, two armchairs, and a wooden coffee table. There are tall, cylindrical columns and a decorative wall with a geometric pattern.

A modern bar area with a long counter, multiple stools, and a bar stocked with bottles.

Sonesta White Plains Downtown

White Plains

10/10 Exceptional

Amy

West Gate Inn Nyack

Nyack

10/10 Exceptional

Maura

A spacious lobby with a fireplace, seating area, and a large wall mural.

A hotel room with a bed, a desk, a wardrobe, and a bathroom.

A modern hotel lobby with a seating area, a reception desk, and a large TV screen.

A large, two-story building with a symmetrical facade, large windows, and a central entrance with a door.

Holiday Inn Express West Point by IHG

Fort Montgomery

10/10 Exceptional

Jennifer

A spacious dining area with multiple tables and chairs, a stone wall with a mounted deer head, and a fireplace.

A large, multi-story stone building with a prominent arched entrance and multiple windows.

A large outdoor swimming pool surrounded by trees and a covered pavilion.

A wooden reception desk with a man standing behind it, a staircase, and a wooden interior.

Overlook Lodge at Bear Mountain

Bear Mountain

10/10 Exceptional

The property is well tucked away in the wilderness of Bear Mountain State Park. It's designed to blend with the surrounding nature. The hotel has very rustic look and feel but in a good way. It definitely gives nostalgic vibes of being in a log and stone cabin in the woods. The rooms and property are very clean and cozy and updated without ruining the rustic feel. The only two complaints I have about the property and it's very minor is that 1) the walls are extremely thin and noise from...

Arie

Frequently Asked Questions

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.

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?

1. Windrose On Hudson

2. Summer Pool Oasis Custom Bar Arcade Pool Table

3. Hotel Nyack, a JdV by Hyatt Hotel

4. Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

5. Courtyard by Marriott Tarrytown Westchester County

6. Baymont by Wyndham White Plains - Elmsford

7. Hotel MTK Mount Kisco

8. Sheraton Tarrytown Hotel

9. West Gate Inn Nyack

10. SpringHill Suites by Marriott Tarrytown Westchester County

11. Sleepy Hollow Hotel, a Dolce by Wyndham

12. Tarrytown House Estate

13. Westchester Marriott

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

15. DoubleTree by Hilton Hotel Nanuet

16. Hampton Inn White Plains/Tarrytown

17. Inn on the Hudson

18. Element by Marriott Spring Valley

19. Days Inn by Wyndham Elmsford / White Plains

20. Hilton Garden Inn Nanuet

Go beyond your typical stay in Ossining

Price trends for hotels in Ossining

October

Top landmarks in Ossining

Travelers Rest

Teatown Lake Reservation

Sing Sing Prison Museum

Kitchawan Preserve

Louis Engel Waterfront Park

Thomas J. Watson Research Center

Ossining Historical Society

Hudson Hills Golf Course

Learn more about Ossining

Check out reviews of Ossining hotels guests love

Windrose On Hudson

10/10 Exceptional

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

10/10 Exceptional

Hotel Nyack, a JdV by Hyatt Hotel

10/10 Exceptional

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

10/10 Exceptional

Courtyard by Marriott Tarrytown Westchester County

10/10 Exceptional

SpringHill Suites by Marriott Tarrytown Westchester County

10/10 Exceptional

DoubleTree by Hilton Hotel Nanuet

10/10 Exceptional

Westchester Marriott

10/10 Exceptional

Hotel MTK Mount Kisco

10/10 Exceptional

Tarrytown House Estate

10/10 Exceptional

Baymont by Wyndham White Plains - Elmsford

10/10 Exceptional

Sheraton Tarrytown Hotel

10/10 Exceptional

The Abbey Inn & Spa

10/10 Exceptional

Cambria Hotel & Suites - White Plains Downtown

10/10 Exceptional

Element by Marriott Spring Valley

10/10 Exceptional

Sonesta White Plains Downtown

10/10 Exceptional

West Gate Inn Nyack

10/10 Exceptional

Holiday Inn Express West Point by IHG

10/10 Exceptional

Overlook Lodge at Bear Mountain

10/10 Exceptional

Frequently Asked Questions

What accommodations do travelers recommend in Ossining?