A wooden boardwalk winding through a forest with autumn foliage.

Search Resort Hotels in Ossining from CA $119

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months
No exact matches found, but these alternatives could be just right

Recommended hotels in Ossining

1. Windrose On Hudson

Windrose On Hudson
3.0 star property
Ossining
8.6 out of 10, Excellent, (283 reviews)
"Would 100% stay again"
United States
Michael
The price is CA $211
CA $235 total
includes taxes & fees
Nov 15 - Nov 16
Windrose On Hudson

2. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is CA $354
CA $413 total
includes taxes & fees
Nov 22 - Nov 23
1BR Queen near NYC | Trails, Biking & Sauna Bliss

3. Near NYC! | Stylish Guestroom

Near NYC! | Stylish Guestroom
Ossining
The price is CA $385
CA $462 total
includes taxes & fees
Nov 22 - Nov 23
Near NYC! | Stylish Guestroom

4. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is CA $685
CA $1,426 total
includes taxes & fees
Nov 9 - Nov 10
Summer Pool Oasis Custom Bar Arcade Pool Table

5. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (10 reviews)
"It's an elegant older house with lots of room for company. Family friendly. The pool was great. My family enjoyed it."
United States
Karen O.
The price is CA $496
CA $1,095 total
includes taxes & fees
Nov 9 - Nov 10
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

6. Polished 1BR w/ Accessible Room Features + Sauna

Polished 1BR w/ Accessible Room Features + Sauna
Ossining
6.0 out of 10, (1 review)
"We could not find location in dark and rain. Only given GPS info and no name of hotel or property. Once we arrived guard at guardhouse could not assist as we could not affirm name. When finally able to track down contact info for the vacation property company that listed the rental they had to share hotel front desk info and that’s when we learned name was Windrose On Hudson. Very stressful situation- enjoyed historical location. Great facility, not so great TV/streaming set-up… cable. "
United States
Nada S.
The price is CA $354
CA $408 total
includes taxes & fees
Nov 15 - Nov 16
Polished 1BR w/ Accessible Room Features + Sauna

7. Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel
4.0 star property
Nyack
8.6 out of 10, Excellent, (1,330 reviews)
"Great stay!"
United States
Kristen
The price is CA $165
CA $227 total
includes taxes & fees
Nov 15 - Nov 16
Hotel Nyack, a JdV by Hyatt Hotel

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

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
2.5 star property
Hawthorne
9.0 out of 10, Wonderful, (1,001 reviews)
"Great stay"
United States
Sean P.
The price is CA $172
CA $197 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

9. Courtyard by Marriott Tarrytown Westchester County

Courtyard by Marriott Tarrytown Westchester County
3.0 star property
Tarrytown
9.0 out of 10, Wonderful, (1,001 reviews)
"Very clean property with pleasant staff."
United States
Syble
The price is CA $213
CA $244 total
includes taxes & fees
Nov 19 - Nov 20
Courtyard by Marriott Tarrytown Westchester County

10. Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
3.5 star property
Tarrytown
8.4 out of 10, Very good, (1,001 reviews)
"clean room, nice and helpful staff"
United States
Jiamin
The price is CA $190
CA $217 total
includes taxes & fees
Nov 22 - Nov 23
Sheraton Tarrytown Hotel

11. Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
2.5 star property
Elmsford
8.2 out of 10, Very good, (1,892 reviews)
"Went for Halloween weekend it was very nice pool was nice as well there a Dunkin’ 3 min walking distance and a 7 min drive to tarry town it was wonderful"
United States
Omari
The price is CA $187
CA $214 total
includes taxes & fees
Nov 29 - Nov 30
Baymont by Wyndham White Plains - Elmsford

12. West Gate Inn Nyack

West Gate Inn Nyack
3.0 star property
Nyack
7.4 out of 10, Good, (1,510 reviews)
"Awesome place will still again if in area"
United States
Joshua
The price is CA $153
CA $174 total
includes taxes & fees
Nov 10 - Nov 11
West Gate Inn Nyack

13. Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham
3.5 star property
Tarrytown
7.0 out of 10, Good, (1,002 reviews)
"Great stay"
United States
Brittany J.
The price is CA $185
CA $212 total
includes taxes & fees
Dec 1 - Dec 2
Sleepy Hollow Hotel, a Dolce by Wyndham

14. DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1,188 reviews)
"Great place"
United States
Joel
The price is CA $177
CA $206 total
includes taxes & fees
Dec 6 - Dec 7
DoubleTree by Hilton Hotel Nanuet

15. SpringHill Suites by Marriott Tarrytown Westchester County

SpringHill Suites by Marriott Tarrytown Westchester County
3.0 star property
Tarrytown
8.8 out of 10, Excellent, (1,007 reviews)
"Clean, friendly staff, would stay again"
United States
Gwen
The price is CA $218
CA $249 total
includes taxes & fees
Nov 15 - Nov 16
SpringHill Suites by Marriott Tarrytown Westchester County

16. Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
3.0 star property
Mount Kisco
8.6 out of 10, Excellent, (1,001 reviews)
"This hotel served our purposes very well."
United States
Joseph
The price is CA $205
CA $235 total
includes taxes & fees
Nov 16 - Nov 17
Hotel MTK Mount Kisco

17. Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown
3.0 star property
Elmsford
7.8 out of 10, Good, (1,727 reviews)
"The room was pretty clean and comfortable, staff was friendly"
United States
Zack
The price is CA $159
CA $181 total
includes taxes & fees
Nov 22 - Nov 23
Hampton Inn White Plains/Tarrytown

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

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
2.5 star property
Peekskill
9.2 out of 10, Wonderful, (1,002 reviews)
"Very clean, great staff, great breakfast."
United States
John
The price is CA $178
CA $204 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

19. Tappan Zee Hotel

Tappan Zee Hotel
2.0 star property
West Nyack
6.6 out of 10, (791 reviews)
"The room was very adequate and the staff were more than helpful. I would stay there again without hesitation."
United States
Robert
The price is CA $103
CA $119 total
includes taxes & fees
Nov 7 - Nov 8
Tappan Zee Hotel

20. Westchester Marriott

Westchester Marriott
4.5 star property
Tarrytown
8.8 out of 10, Excellent, (690 reviews)
"Great stay, clean and close to Sleepy Hollow. Would return again!"
United States
Karrie
The price is CA $250
CA $286 total
includes taxes & fees
Nov 22 - Nov 23
Westchester Marriott
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Ossining Hotel Reviews

Find out more about Ossining

Ossining Resorts information

Number of reviews
5,287
Accommodation
0 Resorts
Lowest Price
CA $119
Highest Price
CA $1,426

Frequently asked questions

What can I expect from a resort vacation in Ossining?
Expedia can help you browse resorts and other lodging options that offer similar services and comforts. If you're having trouble finding a resort in Ossining that works for you, you can use the search page filters to look for hotels, or search for properties that offer amenities like swimming pools or all-inclusive options. We make it simple to book great accommodations so you can focus on planning your trip itinerary.
What's a top resort in Ossining?
Here's our top-rated resort near Ossining: CAM BLISS RETREAT, Only room for one🌹❤️. - 15.3 mi (24.6 km) from Ossining. Features a sauna.
What can I do in Ossining?
Learn about the local history at monuments like Thomas J. Watson Research Center, or bring the kids to Labyrinth for some family fun. Sing Sing Prison Museum and Ossining Historical Society are a few additional attractions in the area that you might like.
What's the weather like in Ossining?
The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 34°F. Average annual precipitation for Ossining is 51 inches.
What's the best way to get to and around Ossining?
Fly into Westchester County Airport (HPN), which is located 10.5 mi (16.8 km) away from the city center. Otherwise, look for flights into Teterboro, NJ (TEB), which is 23.9 mi (38.5 km) away. To venture out into the surrounding area, hop aboard a train at Ossining Station.

Explore a world of travel with Expedia