Ossining Holiday Rentals, New York: Private House Rentals

A wooden boardwalk winding through a forest with autumn foliage.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Ossining

Pet friendly

Apartment

Pool

Spa

Hot tub

Family friendly

Cottage

Waterpark

Condo

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Ossining hotels

A hotel room with a large bed, two bedside lamps, a nightstand, a blue chair, and a view of greenery through the window.

A spacious outdoor dining area with multiple tables and chairs, large blue umbrellas, and a view of greenery and buildings in the background.

A building with a brick facade, a covered entrance, and a well-maintained lawn with a bush.

A conference room with a large screen displaying a building image, a whiteboard, and a table with laptops, papers, and coffee cups.

1. Windrose On Hudson

Ossining

Rachel

4.823.187 ₫

5.371.920 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A hallway with hardwood flooring, a staircase, and a dining area with a chair and table.

A spacious living room with hardwood floors, a black leather sofa, a wooden desk, and a computer chair.

A living room with a sofa, a rug, a lamp, and artwork on the wall.

A patio with stone tiles, a table with chairs, and a grill.

2. Snow Days & City Escapes: Spacious Ossining Home

Ossining

7.510.243 ₫

21.641.714 ₫ total

includes taxes & fees

21 Oct - 22 Oct

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

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

3. Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

14.987.633 ₫

29.674.022 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

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

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.

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

Hawthorne

CHRISTY

3.847.112 ₫

4.400.135 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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

A modern hotel lobby with a seating area, a kitchen, and a bar.

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

5. Baymont by Wyndham White Plains - Elmsford

Elmsford

Ebony

3.513.089 ₫

4.018.096 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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.

6. Hotel Nyack, a JdV by Hyatt Hotel

Nyack

Jessica

3.105.738 ₫

4.256.364 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

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

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

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

7. West Gate Inn Nyack

Nyack

Dale

3.014.232 ₫

3.447.435 ₫ total

includes taxes & fees

15 Oct - 16 Oct

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

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

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

An indoor swimming pool with a wooden ceiling and brick walls.

8. Sleepy Hollow Hotel, a Dolce by Wyndham

Tarrytown

Michelle

3.560.220 ₫

4.072.002 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

A hotel room with a bed, a desk with a chair, a TV, and artwork on the walls.

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.

9. SpringHill Suites by Marriott Tarrytown Westchester County

Tarrytown

Malisa

4.046.956 ₫

4.628.706 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

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

A courtyard with a fire pit, outdoor seating, and modern apartment buildings.

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.

10. Courtyard by Marriott Tarrytown Westchester County

Tarrytown

Justine

4.185.034 ₫

4.786.632 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

11. Westchester Marriott

Tarrytown

Robert

4.838.783 ₫

5.534.357 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

A gym with treadmills, elliptical machines, and weightlifting equipment.

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

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

12. Hampton Inn White Plains/Tarrytown

Elmsford

Susan

3.114.341 ₫

3.562.029 ₫ total

includes taxes & fees

5 Nov - 6 Nov

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

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

A modern office space with two monitors, a white desk, black chairs, and a large abstract painting on the wall.

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

13. Sheraton Tarrytown Hotel

Tarrytown

Andrew

3.722.341 ₫

4.257.428 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

A coffee station with multiple coffee dispensers, a hot water station, and various coffee products on shelves.

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.

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

Peekskill

Edwin

3.873.106 ₫

4.429.867 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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

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.

15. Tarrytown House Estate

Tarrytown

RAMESH

4.392.986 ₫

5.674.230 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

A hotel entrance with a covered walkway, stone pillars, and potted plants.

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

16. Hotel MTK Mount Kisco

Mount Kisco

Patricia

4.028.550 ₫

4.607.653 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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 restaurant interior with a bar area, seating, and a dessert display.

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

A hotel lobby with a reception desk, seating area, and a large window allowing natural light.

17. DoubleTree by Hilton Hotel Nanuet

Nanuet

Linda

3.513.089 ₫

4.088.357 ₫ total

includes taxes & fees

27 Oct - 28 Oct

A hotel room with two beds, a desk, a TV, and a mirror.

A spacious lobby with a seating area, a coffee station, and a staircase leading to an upper floor.

A sign for Nyack Motor Lodge with blooming trees in the foreground.

18. Tappan Zee Hotel

West Nyack

Salim

2.913.922 ₫

3.391.303 ₫ total

includes taxes & fees

7 Oct - 8 Oct

A hotel entrance with a sign reading "SONESTA Simply Suites".

A covered outdoor area with a wooden deck, metal chairs, a round table, and hanging flower baskets.

A hotel room with a bed, a desk, a chair, a TV, and a lamp.

A compact kitchen with a dining area, a flat-screen TV, a microwave, a coffee maker, and a refrigerator.

19. Sonesta Simply Suites Nanuet

Nanuet

Susan

3.065.212 ₫

3.567.142 ₫ total

includes taxes & fees

14 Oct - 15 Oct

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

A gym with treadmills, exercise balls, and a yoga mat.

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

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

20. Days Inn by Wyndham Elmsford / White Plains

Elmsford

Cherish

2.770.960 ₫

3.260.263 ₫ total

includes taxes & fees

1 Nov - 2 Nov

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Ossining attractions

A dam with a reservoir, surrounded by autumn foliage and hills.

Travelers Rest

This historic former stagecoach stop serves exceptional American and German cuisine in elegant, fireplace-lit dining rooms. Stroll through the landscaped gardens with waterfalls before your memorable meal.

See properties

A misty lake surrounded by trees with sunlight filtering through the leaves.

Teatown Lake Reservation

This 1,000-acre nature preserve features diverse ecosystems along scenic trails. Explore the floating boardwalk across the lake for wildlife viewing and see the island's native wildflower collection.

See properties

Ossining Historical Society

This intimate museum preserves Ossining's heritage through artefacts connected to Sing Sing Prison and local history. Schedule a personalised appointment for the most enriching exploration of this community treasure.

See properties

Kitchawan Preserve

Explore the great outdoors at Kitchawan Preserve, a lovely green space in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

See properties

Sing Sing Prison Museum

Step inside America's most infamous prison at the Sing Sing Prison Museum, opening in 2025 for its 200th anniversary. Explore artefacts and stories illuminating incarceration and rehabilitation in America.

See properties

Louis Engel Waterfront Park

Louis Engel Waterfront Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

See properties

Merchants Square

9.0/10 (2 reviews)

Explore the great outdoors at Merchants Square, a lovely green space in Ossining. Stroll along the riverfront or attend a sporting event in this quaint area.

See properties

Hudson Hills Golf Course

Nestled in Ossining's rolling terrain, this Mark Mungeam-designed course challenges players with strategic bunkers and undulating fairways. Enjoy Hudson River Valley views while navigating the thoughtful 18 holes.

See properties

Learn more about Ossining

Sing Sing Prison Museum offers a fascinating glimpse into America's most notorious correctional facility, with guided tours by former officers. Hike the scenic Old Croton Aqueduct Trail and then grab lunch at one of the diverse restaurants along the Hudson River waterfront.

See all hotels in Ossining

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

Top Ossining Hotel Reviews

West Gate Inn Nyack

10/10 Excellent

"Over all vey good experience"

Baymont by Wyndham White Plains - Elmsford

10/10 Excellent

"Just really a nice layout!"

Clinton Inn Hotel & Event Center

10/10 Excellent

"The hotel is convenient and safe. You can walk to the charming town center of Tenafly. The staff was very helpful. It is a quaint hotel, clean. A little outdated in decor, but I slept very well."

Amsterdam Hotel

10/10 Excellent

"My room was perfect, and the staff were very helpful and kind."

LIV Hotel Bronx - Newly Built

8/10 Good

"Property has been refurbished and like new."

Royal Hotel Bronx

8/10 Good

"Deben de tener estacionamiento propio para huéspedes"

Sleepy Hollow Hotel, a Dolce by Wyndham

8/10 Good

"Great stay overall. Could use small repairs here and there but I’m a developer by trade so I notice small things. Overall happy with our stay but a little further from town than we would have liked"

J House Greenwich

8/10 Good

"Great stay loved the room and the tv in the bathroom mirror was amazing. We ate at Tony’s restaurant while there which was fantastic. My only complaint and area of improvement was the breakfast provided in the AM was awful. Just a few baked pastries,granola bars and yogurt provided. Basically something to grab and go but not sure can really be counted as “breakfast included” other than that though we loved the room and property."

Hyatt Regency Greenwich

10/10 Excellent

"We were very happy to see the Hyatt back up and running in full service form. We've stayed pre-, during, and post-COVID and this was just great. I have to give kudos to PAMELA at the front desk who actually recognized me!! She is an incredible and valuable employee. It was so, so nice to see her again--that great smile, professionalism and nice personality."

More cheap stays in Ossining

Red Carpet Inn

1209 E Main St Stamford CT

2.276.201 ₫

2.617.670 ₫ total

7 Oct - 8 Oct

includes taxes & fees

Overlook Lodge at Bear Mountain

55 Hessian Drive Bear Mountain NY

2.263.427 ₫

2.786.844 ₫ total

3 Nov - 4 Nov

includes taxes & fees

Hilltop Inn & Suites

125 Tuckahoe Rd Yonkers NY

2.475.148 ₫

2.914.487 ₫ total

1 Nov - 2 Nov

includes taxes & fees

Amsterdam Hotel

19 Clarks Hill Ave Stamford CT

2.737.688 ₫

3.172.308 ₫ total

5 Nov - 6 Nov

includes taxes & fees

8.4/10 Very good! (1,802 reviews)

Hampton Inn & Suites Yonkers - Westchester

559 Tuckahoe Rd Yonkers NY

2.966.175 ₫

3.492.672 ₫ total

1 Nov - 2 Nov

includes taxes & fees

9/10 Wonderful! (1,216 reviews)

Baymont by Wyndham White Plains - Elmsford

540 Saw Mill River Rd Elmsford NY

3.513.089 ₫

4.018.096 ₫ total

2 Nov - 3 Nov

includes taxes & fees

8.4/10 Very good! (1,877 reviews)

Hotels in Ossining with star rating

Frequently asked questions

What's the weather like in Ossining?

The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 1°C. Average annual precipitation for Ossining is 1302 mm.

Find hotels in Ossining, NY from 2.617.670 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Ossining

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Ossining hotels

1. Windrose On Hudson

2. Snow Days & City Escapes: Spacious Ossining Home

3. Summer Pool Oasis Custom Bar Arcade Pool Table

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

5. Baymont by Wyndham White Plains - Elmsford

6. Hotel Nyack, a JdV by Hyatt Hotel

7. West Gate Inn Nyack

8. Sleepy Hollow Hotel, a Dolce by Wyndham

9. SpringHill Suites by Marriott Tarrytown Westchester County

10. Courtyard by Marriott Tarrytown Westchester County

11. Westchester Marriott

12. Hampton Inn White Plains/Tarrytown

13. Sheraton Tarrytown Hotel

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

15. Tarrytown House Estate

16. Hotel MTK Mount Kisco

17. DoubleTree by Hilton Hotel Nanuet

18. Tappan Zee Hotel

19. Sonesta Simply Suites Nanuet

20. Days Inn by Wyndham Elmsford / White Plains

Stay near popular Ossining attractions

Travelers Rest

Teatown Lake Reservation

Ossining Historical Society

Kitchawan Preserve

Sing Sing Prison Museum

Louis Engel Waterfront Park

Merchants Square

Hudson Hills Golf Course

Learn more about Ossining

Top Ossining Hotel Reviews

West Gate Inn Nyack

Baymont by Wyndham White Plains - Elmsford

Clinton Inn Hotel & Event Center

Amsterdam Hotel

LIV Hotel Bronx - Newly Built

Royal Hotel Bronx

Sleepy Hollow Hotel, a Dolce by Wyndham

J House Greenwich

Hyatt Regency Greenwich

More cheap stays in Ossining

Red Carpet Inn

Overlook Lodge at Bear Mountain

Hilltop Inn & Suites

Amsterdam Hotel

Hampton Inn & Suites Yonkers - Westchester

Baymont by Wyndham White Plains - Elmsford

Hotels in Ossining with star rating

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app