A wooden boardwalk winding through a forest with autumn foliage.

Find 5 Star Hotels in Ossining, NY from $171

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Ossining 5 Star Hotels

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

Our top choices for Ossining 5-star hotels

Exterior

1. The Opus Westchester, Autograph Collection

The Opus Westchester, Autograph Collection
5.0 star property
White Plains
9.2 out of 10, Wonderful, (573 reviews)
"Amazing stay. Will be visiting again. "
United States
Vann
$349 nightly
The price is $399
Aug 6 - Aug 7
Total with taxes and fees
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
$195 nightly
The price is $223 total per night from Aug 30 to Aug 31
$223 total
Aug 30 - Aug 31
Total with taxes and fees
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
A historic stone building with a large circular window and a tower with a green roof.
Photo by louann ohora
Open Photo by louann ohora

Top Ossining Hotel Reviews

Find out more about Ossining

Why not request the best of accommodations during your excursion to Ossining? After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Ossining so popular in the last year. There's no reason to delay a getaway to Ossining any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Book one of Expedia's luxurious 5-star hotels in Ossining and get ready to enjoy the getaway of a lifetime. What are you waiting for?

Get a Great Deal on 5-Star Hotels in Ossining

You'll have a wonderful time at one of these 5-star hotels. Exceptional customer care, luxurious bedding, and deeply relaxing spa offerings are waiting for you. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready for a wonderful adventure. What creature comforts do you want in your lodging? 24-hour room service, so you can order that filet mignon in the wee hours of the morning? A body scrub that will leave you feeling like a million bucks? Butler services? Whatever it is your heart desires, you're bound to find it here.

But you aren't going to spend your entire vacation in your room, of course. Don't worry. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. Whatever you plan to do, the 5-star hotels in Ossining are waiting for you to relax after a busy day. Ready to learn more? Then check out our listings and pick the perfect accommodation for your needs.

Make Your Escape

The results are in, and Ossining 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. It's time to plan your next great escape. Choose one of Expedia's Ossining 5-star hotels today and relax in luxe surroundings tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Ossining?
The amount you pay for a 5-star hotel in Ossining can vary based on when you prefer to travel and how long you plan to be away, among a number of factors. Take advantage of our price per night filter and other search tools to find the best rate on a high-end stay.

  • Search for the lowest price per night from $171

What makes a hotel 5 stars in Ossining?
Exceptional guest service is integral to every 5-star hotel in Ossining. From the second you arrive, staff ensure your every need is met, whether arranging valet parking or providing a turn-down service. Plus, hotels must offer top-rate amenities to be entitled to a 5-star rating. These can include luxury toiletries, an on-site spa, pools, gastronomic kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Ossining?
Use Expedia's filter tool to find a high-end retreat in Ossining where everything you need is included. After your initial search, refine your results for properties that have 5 stars and are categorized as "All inclusive." The first thing on the to-do list at these stays? Pure relaxation and indulgence.

Explore a world of travel with Expedia