Ossining Holiday Rentals, New York: Private House Rentals

A wooden boardwalk winding through a forest with autumn foliage.

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

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

A stone fireplace with a fire, surrounded by outdoor seating.

1. Windrose On Hudson

Ossining

Rachel

4.823.001 ₫

5.371.713 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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 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.

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

2. Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

17.841.677 ₫

32.852.214 ₫ total

includes taxes & fees

14 Sept - 15 Sept

A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

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

A dining area with a long wooden table, yellow placemats, and orange chairs. There is a ceiling light fixture above the table.

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

3. Nyc-area Escape Near River, Trails & Mta!

Ossining

7.079.436 ₫

21.133.802 ₫ total

includes taxes & fees

15 Sept - 16 Sept

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.

4. Baymont by Wyndham White Plains - Elmsford

Elmsford

Ebony

3.292.013 ₫

3.765.240 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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 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.

5. Hampton Inn White Plains/Tarrytown

Elmsford

Susan

2.941.368 ₫

3.364.187 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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 flat-screen TV on a wooden dresser, a sofa, a bed with a white headboard, and two abstract paintings on the walls.

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.

6. SpringHill Suites by Marriott Tarrytown Westchester County

Tarrytown

Justin

3.595.612 ₫

4.112.480 ₫ total

includes taxes & fees

17 Sept - 18 Sept

A spacious lounge area with comfortable seating, a bar with a well-stocked shelf, and a modern ceiling design.

A spacious lobby with seating areas, a reception desk, and a large plant.

A multi-story hotel with a prominent 'Hyatt House' sign, surrounded by well-maintained lawns and trees.

A spacious dining area with multiple seating options including booths and tables, a kitchen area in the background, and a modern interior design.

7. HYATT house White Plains

West Harrison

Lynn

5.056.740 ₫

5.783.645 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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 modern breakfast bar with a variety of food options, including cereal and hot food. There are signs indicating breakfast and hot food availability.

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

Hawthorne

Wanda

3.613.027 ₫

4.132.399 ₫ total

includes taxes & fees

20 Sept - 21 Sept

A multi-story hotel with a prominent sign reading "Hyatt Place".

A hotel room with a large bed, a desk, a chair, and a window with curtains.

A modern hotel lobby with a fireplace, seating area, and a desk with a computer.

A modern bar area with wooden cabinets, a refrigerated display case, and bar stools.

9. Hyatt Place New York/Yonkers

Southeast Yonkers

Linda

3.742.992 ₫

4.498.350 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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.

10. Westchester Marriott

Tarrytown

Donna

5.047.664 ₫

5.773.265 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A hotel patio with outdoor seating, a fire pit, and a covered area with glass doors.

An indoor swimming pool with a 'NO DIVING' sign, lounge chairs, and a lifeguard chair.

A modern living room with a fireplace, a bookshelf, and comfortable seating.

A modern lobby with a fireplace, bookshelves, and a seating area.

11. Residence Inn Orangeburg

Orangeburg

paul

4.644.421 ₫

5.172.725 ₫ total

includes taxes & fees

24 Sept - 25 Sept

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

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

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

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

12. Tarrytown House Estate

Tarrytown

Ariana

4.123.188 ₫

5.364.294 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A modern restaurant with a bar area, multiple seating options including tables and booths, and a view of greenery outside.

A reception area with a modern design, featuring a counter, a wall with text, and a refrigerator stocked with beverages.

An outdoor patio with a stone wall, a built-in bench, and a fire pit surrounded by chairs.

A modern hotel with a flat roof, a covered entrance, and a landscaped driveway.

13. SpringHill Suites by Marriott Tuckahoe Westchester County

Tuckahoe

Jonathan

3.954.835 ₫

4.523.343 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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.

14. Hotel Nyack, a JdV by Hyatt Hotel

Nyack

Adam

3.261.069 ₫

4.433.997 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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.

15. Sonesta White Plains Downtown

White Plains

Corinthia

4.188.018 ₫

5.650.210 ₫ total

includes taxes & fees

4 Oct - 5 Oct

An indoor swimming pool with clear glass ceilings, stone walls, and multiple lounge chairs around the pool area.

A spacious lobby with a central seating area, a decorative wall, and a reception desk in the background.

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

A hotel room with a large bed, a bedside table with a lamp, a TV, and a bathroom with a mirror and sink.

16. DoubleTree by Hilton Hotel Nanuet

Nanuet

Linda

3.069.253 ₫

3.571.842 ₫ total

includes taxes & fees

20 Sept - 21 Sept

A spacious hotel dining area with a long table, multiple chairs, and modern pendant lighting.

A hotel room with a large flat-screen TV, a desk with a lamp, a chair, and a sofa. There are artworks on the wall and a window with blinds.

A store interior with shelves stocked with snacks and drinks, a refrigerated section, and a wall sign labeled "TREATS".

A Hampton Inn & Suites building with a brick facade, large windows, and a covered entrance area.

17. Hampton Inn & Suites Yonkers - Westchester

Northeast Yonkers

Cheri

3.175.825 ₫

3.739.533 ₫ total

includes taxes & fees

4 Oct - 5 Oct

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 hotel room with two beds, a desk with a television, and a window with curtains.

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.

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

Peekskill

David

3.915.732 ₫

4.478.619 ₫ total

includes taxes & fees

13 Sept - 14 Sept

An outdoor patio area with stone flooring, seating arrangements, and a fire pit.

A hotel room with a bed, a desk, a chair, a TV, and a window with a view of buildings.

A Courtyard Marriott hotel with multiple floors, a parking lot, and a covered entrance.

A modern lounge area with leather armchairs, a round coffee table, a sofa, and a large abstract painting on the wall.

19. Courtyard by Marriott Yonkers Westchester County

Northwest Yonkers

Toron

3.500.820 ₫

4.122.216 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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 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.

20. West Gate Inn Nyack

Nyack

Marcelo

2.567.009 ₫

2.936.021 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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Stay near popular Ossining attractions

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.

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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.

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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.

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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.

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Nelson Park

Nelson Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Stroll along the riverfront in this quaint area or visit its top-notch restaurants.

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Ossining Public Library

Learn about the local history of Ossining when you take a trip to Ossining Public Library. Amble around the area's parks or visit its monuments.

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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.

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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.

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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 historic stone building with a large circular window and a tower with a green roof.

Top Ossining Hotel Reviews

West Gate Inn Nyack

8/10 Good

"Very welcoming staff - at desk - night and day and breakfast staff! Good food nearby at Nyack Diner Internet and Shower worked well Only negative was that I couldn’t figure out how to work tv"

Sonesta White Plains Downtown

10/10 Excellent

"I walked into a magnificent lobby that was brightly lit and spacious. Room service was great and the mall across the street has a lovely food court. My room was comfy, roomy and spotless! A 10 out of 10 for me!"

Windrose On Hudson

10/10 Excellent

"Quick stop in a spacious, clean hotel with friendly helpful staff. Thank you 💕"

La Quinta Inn & Suites by Wyndham Stamford / New York City

8/10 Good

"La Quinta Stamford offered a covenient location and price for stopping over on our way from New Hampshire to the D.C area. We arrived late at night and left early the next morning, unfortunately missing the convenient continental breakfast [so cannot comment on that]. Staff was friendly and efficient, very pleasant. The facility was a bit shabby, with worn areas of walls and doors, and the pretty pool surrounded by shipping boxes piled from floor to ceiling, but our room was clean and spacious, and bed and pillow very comfortable for a great night’s sleep. The bathroom was exceptionally clean with a sparkling and very enjoyable bathtub."

Ethan Allen Hotel

8/10 Good

"Upon arrival I asked for the pack and play I had called beforehand and requested and the manager to the staff helping me goes, “is there a note? Was it requested beforehand?” It was, but what if it wasn’t? Then I asked the front desk staff if I could have a room away from elevators and stairs and the manager, again from off to the side, goes, “we’re really booked right now with a wedding and a hockey team.” I go, “ok well I have a baby so just away from the hockey team would be great.” She goes on to say they can’t accommodate such things yadda yadda - then the front desk staff looks at me and goes, “I gave you a room in the middle of the floor away from stairs and elevators.” So not sure if the manager was just trying to find an issue or what. The elevator is inconveniently located on the complete opposite side of the hotel as the lobby and our room. The stairs were quick and easily accessible but because I had a stroller, I had to walk around 3 sides of the hotel. Get to our room - dirty stained carpet but otherwise clean. The tub and toilet were both clogged when we got there. I asked for them to be unclogged and left but the maintenance man only unclogged the toilet. When the pack and play arrived, I asked if I could have an extra towel and wash cloth for my baby and was told no by the housekeeper. In the middle of the night 4 ants were crawling on the toilet (I have pictures and video), the heat/ac unit front fell off everytime it kicked on. Hotel was nice, bad room."

Ramada by Wyndham Bronx

8/10 Good

"The hotel is great. Always clean, always smells nice and is well kept. And most of the staff is really good. But the lady from the kitchen who makes the waffles has a DISGUSTING attitude. I noticed the last couple times I stayed at the hotel, she particularly treats the certain guests better than she treats the other guests. The certain guests get waited on hand and foot and are treated like Kings and Queens, while the other guests (such as myself) do not get greeted and are not welcomed with the same warmth. The staff at the Front Desk is always warm and welcoming, which is one of the reasons I continue to come back. In my opinion, the lady from the kitchen should be removed from Food duties at this facility. It is a shame that in 2026 other guests are made to feel inferior, unwanted, unwelcome and disrespected. I do hope upper management looks into this particular staff member and overseas her treatment of the guests as they frequent the kitchen. I normally would not leave bad reviews, but this is the third time I have witnessed everything I’m describing by this particular staff member. I do hope something is done about this behavior immediately."

Westchester Marriott

10/10 Excellent

"LIKED EVERYTHING."

Amsterdam Hotel

10/10 Excellent

"Thank you!"

More cheap stays in Ossining

Amsterdam Hotel

19 Clarks Hill Ave Stamford CT

2.307.948 ₫

2.677.998 ₫ total

28 Sept - 29 Sept

includes taxes & fees

8.4/10 Very good! (1,773 reviews)

Hilltop Inn & Suites

125 Tuckahoe Rd Yonkers NY

2.361.887 ₫

2.781.121 ₫ total

11 Oct - 12 Oct

includes taxes & fees

7.6/10 Good! (1,081 reviews)

Red Carpet Inn

1209 E Main St Stamford CT

2.458.094 ₫

2.826.847 ₫ total

13 Sept - 14 Sept

includes taxes & fees

Overlook Lodge at Bear Mountain

55 Hessian Drive Bear Mountain NY

2.958.192 ₫

3.642.275 ₫ total

13 Sept - 14 Sept

includes taxes & fees

8.4/10 Very good! (1,000 reviews)

Hampton Inn & Suites Yonkers - Westchester

559 Tuckahoe Rd Yonkers NY

3.175.825 ₫

3.739.533 ₫ total

4 Oct - 5 Oct

includes taxes & fees

9/10 Wonderful! (1,178 reviews)

Baymont by Wyndham White Plains - Elmsford

540 Saw Mill River Rd Elmsford NY

3.292.013 ₫

3.765.240 ₫ total

20 Sept - 21 Sept

includes taxes & fees

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 2.677.998 ₫

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. Summer Pool Oasis Custom Bar Arcade Pool Table

3. Nyc-area Escape Near River, Trails & Mta!

4. Baymont by Wyndham White Plains - Elmsford

5. Hampton Inn White Plains/Tarrytown

6. SpringHill Suites by Marriott Tarrytown Westchester County

7. HYATT house White Plains

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

9. Hyatt Place New York/Yonkers

10. Westchester Marriott

11. Residence Inn Orangeburg

12. Tarrytown House Estate

13. SpringHill Suites by Marriott Tuckahoe Westchester County

14. Hotel Nyack, a JdV by Hyatt Hotel

15. Sonesta White Plains Downtown

16. DoubleTree by Hilton Hotel Nanuet

17. Hampton Inn & Suites Yonkers - Westchester

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

19. Courtyard by Marriott Yonkers Westchester County

20. West Gate Inn Nyack

Stay near popular Ossining attractions

Teatown Lake Reservation

Travelers Rest

Hudson Hills Golf Course

Sing Sing Prison Museum

Nelson Park

Ossining Public Library

Ossining Historical Society

Merchants Square

Learn more about Ossining

Top Ossining Hotel Reviews

West Gate Inn Nyack

Sonesta White Plains Downtown

Windrose On Hudson

La Quinta Inn & Suites by Wyndham Stamford / New York City

Ethan Allen Hotel

Ramada by Wyndham Bronx

Westchester Marriott

Amsterdam Hotel

More cheap stays in Ossining

Amsterdam Hotel

Hilltop Inn & Suites

Red Carpet Inn

Overlook Lodge at Bear Mountain

Hampton Inn & Suites Yonkers - Westchester

Baymont by Wyndham White Plains - Elmsford

Hotels in Ossining with star rating

Frequently asked questions

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