Photo by louann ohora

Ossining Hotel Guide - 5 Stars Hotels in Ossining, New York

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Check availability on Ossining 5 Star Hotels

Our top choices for Ossining 5-star hotels

Exterior
The Opus Westchester, Autograph Collection

The Opus Westchester, Autograph Collection

The Opus Westchester, Autograph Collection
5.0 star property
White Plains
9.2 out of 10, Wonderful, (528)
"our room was very clean on beds very comfortable staff friendly, breakfast wonderful"
United States
Susan
The price is Rp5.000.177
Rp6.292.719 total
includes taxes & fees
21 Dec - 22 Dec
The Opus Westchester, Autograph Collection
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Ossining.
Sonesta White Plains Downtown

Sonesta White Plains Downtown

66 Hale Ave White Plains NY
The price is Rp2.642.234 per night from 8 Jan to 9 Jan
Rp2.642.234
Rp3.576.758 total
8 Jan - 9 Jan 2026
includes taxes & fees
8.6/10 Excellent! (1,153 reviews)
Still don't see what you're looking for?
See all properties in Ossining.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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.

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
Main building at Maryknoll
Photo by louann ohora
Open Photo by louann ohora

Top Ossining Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Ossining?
You'll find many different pricing options for a 5-star hotel in Ossining on Expedia. The amount you pay will depend on when you want to travel, trip length and other factors. Compare all of the available properties for your preferred dates and use our pricing and other filters to find the ideal upscale stay.

  • Search for the lowest price per night from Rp2.787.898

What makes a hotel 5 stars in Ossining?
In Ossining, a hotel must offer a specific number of upscale amenities to be rated 5 stars. These can include gourmet restaurants, on-site gyms, saunas and spas, luxury bathroom products, premium bedding and more. What also sets 5-star hotels apart is their guest-focused service. You'll enjoy things like concierge services, nightly turn-down services and in-room massage. Some may also offer thoughtful touches like welcome gifts.
Are there any 5-star all-inclusive resorts in Ossining?
Use Expedia's filters to find a luxurious retreat in Ossining where everything you need is included in the price. Next, narrow down your results for properties that have a 5-star rating and are described as "All inclusive." The most important thing on the agenda at these stays? Relaxation and enjoyment.