Search Chalets in Ossining from CA $153

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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 $212
CA $236 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 $355
CA $409 total
includes taxes & fees
Nov 15 - Nov 16
1BR Queen near NYC | Trails, Biking & Sauna Bliss

3. Near NYC! | Stylish Guestroom

Near NYC! | Stylish Guestroom
Ossining
The price is CA $386
CA $446 total
includes taxes & fees
Nov 15 - Nov 16
Near NYC! | Stylish Guestroom

4. 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!

5. 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 $688
CA $1,430 total
includes taxes & fees
Nov 9 - Nov 10
Summer Pool Oasis Custom Bar Arcade Pool Table

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 $413 total
includes taxes & fees
Nov 22 - Nov 23
Polished 1BR w/ Accessible Room Features + Sauna

7. 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, (1,003 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

8. 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

9. West Gate Inn Nyack

West Gate Inn Nyack
3.0 star property
Nyack
7.4 out of 10, Good, (1,513 reviews)
"Awesome place will still again if in area"
United States
Joshua
The price is CA $153
CA $175 total
includes taxes & fees
Nov 8 - Nov 9
West Gate Inn Nyack

10. 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

11. Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
3.5 star property
Tarrytown
8.4 out of 10, Very good, (1,003 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

12. Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
2.5 star property
Elmsford
8.2 out of 10, Very good, (1,893 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 $188
CA $215 total
includes taxes & fees
Nov 29 - Nov 30
Baymont by Wyndham White Plains - Elmsford

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, (1,006 reviews)
"Great stay"
United States
Brittany J.
The price is CA $186
CA $213 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 $207 total
includes taxes & fees
Dec 7 - Dec 8
DoubleTree by Hilton Hotel Nanuet

15. Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown
3.0 star property
Elmsford
7.8 out of 10, Good, (1,728 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

16. 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 22 - Nov 23
SpringHill Suites by Marriott Tarrytown Westchester County

17. 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, (1,003 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

18. Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
3.0 star property
Mount Kisco
8.6 out of 10, Excellent, (1,003 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

19. Tarrytown House Estate

Tarrytown House Estate
3.5 star property
Tarrytown
8.2 out of 10, Very good, (1,423 reviews)
"It was a beautiful place to stay"
United States
Brooke
The price is CA $279
CA $354 total
includes taxes & fees
Nov 8 - Nov 9
Tarrytown House Estate

20. Westchester Marriott

Westchester Marriott
4.5 star property
Tarrytown
8.8 out of 10, Excellent, (691 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.

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.

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

Top reviews in Ossining

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