Photo by louann ohora

Search Resorts in Ossining

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 prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Resorts in Ossining

No exact matches found, but these alternatives could be just right

Recommended hotels in Ossining

Terrace/patio
Windrose On Hudson

Windrose On Hudson

3.0 star property
Ossining
8.0 out of 10, Very Good, (94)
"Clean rooms, quiet, beautiful grounds"
United States
patricia
The price is SAR 549
SAR 611 total
includes taxes & fees
14 Dec - 15 Dec
Windrose On Hudson
Interior
1BR Queen near NYC | Trails, Biking & Sauna Bliss

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

2.0 star property
Ossining
The price is SAR 1,047
SAR 1,394 total
includes taxes & fees
3 Dec - 4 Dec
1BR Queen near NYC | Trails, Biking & Sauna Bliss
House | 5 bedrooms
Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow

2.0 star property
Ossining
The price is SAR 1,593
SAR 3,547 total
includes taxes & fees
8 Dec - 9 Dec
Foliage at Westchester Manor - Near Sleepy Hollow
Outdoor banquet area
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

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

Ossining
9.0 out of 10, Wonderful, (6)
"We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again. "
United States
Matthew W.
The price is SAR 3,073
SAR 5,172 total
includes taxes & fees
8 Dec - 9 Dec
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Interior
Polished 1BR w/ Accessible Room Features + Sauna

Polished 1BR w/ Accessible Room Features + Sauna

2.0 star property
Ossining
The price is SAR 1,047
SAR 1,390 total
includes taxes & fees
3 Dec - 4 Dec
Polished 1BR w/ Accessible Room Features + Sauna
Interior
Near NYC! | Stylish Guestroom

Near NYC! | Stylish Guestroom

2.0 star property
Ossining
The price is SAR 1,137
SAR 1,451 total
includes taxes & fees
3 Dec - 4 Dec
Near NYC! | Stylish Guestroom
Deluxe Room, 1 King Bed, Non Smoking | Desk, laptop workspace, free WiFi, bed sheets
LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

3.0 star property
Bronx
8.2 out of 10, Very Good, (184)
"Nice hotel Great price 10/10"
United States
Lennie
The price is SAR 436
SAR 513 total
includes taxes & fees
2 Dec - 3 Dec
LIV Hotel Bronx - Newly Built
Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1023)
"Parking was very easy, beautiful area, very nice staff"
United States
Elizabeth
The price is SAR 384
SAR 434 total
includes taxes & fees
7 Dec - 8 Dec
Overlook Lodge at Bear Mountain
Lobby
Comfort Inn Brewster

Comfort Inn Brewster

2.5 star property
Brewster
9.0 out of 10, Wonderful, (516)
"Clean room, nice staff"
United States
Margaret
The price is SAR 443
SAR 480 total
includes taxes & fees
14 Dec - 15 Dec
Comfort Inn Brewster
Two Double Beds, Non Smoking | Desk, iron/ironing board, free WiFi, bed sheets
Hilltop Inn & Suites

Hilltop Inn & Suites

2.5 star property
Northwest Yonkers
7.0 out of 10, Good, (516)
"I always have a good stay at the hilltop. Service is great breakfast is great staff is great"
United States
Ronald
The price is SAR 357
SAR 420 total
includes taxes & fees
7 Dec - 8 Dec
Hilltop Inn & Suites
Interior
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 star property
Suffern
8.8 out of 10, Excellent, (1022)
"One of the best Hotel in Rockland, everything was clean "
United States
Kenson
The price is SAR 387
SAR 451 total
includes taxes & fees
1 Jan - 2 January 2026
Crowne Plaza Suffern - Mahwah by IHG
Daily full breakfast (USD 18 per person)
Ethan Allen Hotel

Ethan Allen Hotel

3.5 star property
Danbury
7.8 out of 10, Good, (1071)
"Great Hotel!"
United States
Steven
Ethan Allen Hotel
Lobby
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1025)
"Staff were friendly and very helpful and the hotel was well cared after. "
United States
Jason
The price is SAR 357
SAR 440 total
includes taxes & fees
11 Dec - 12 Dec
Hampton Inn Harriman Woodbury
Lobby
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4.0 star property
Nanuet
8.8 out of 10, Excellent, (1016)
"Very clean very beautiful very good hospitality would stay again"
United States
Bobby
The price is SAR 397
SAR 462 total
includes taxes & fees
14 Dec - 15 Dec
DoubleTree by Hilton Hotel Nanuet
Lobby
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, (1020)
"Room was clean, staff was pleasant, hotel overall was great"
United States
Cara
The price is SAR 348
SAR 499 total
includes taxes & fees
15 Dec - 16 Dec
Hotel Nyack, a JdV by Hyatt Hotel
Interior
Royal Regency Hotel

Royal Regency Hotel

3.5 star property
Northwest Yonkers
8.4 out of 10, Very Good, (2408)
"Hotel was very clean and the staff are great"
United States
Marie and Matt
The price is SAR 369
SAR 453 total
includes taxes & fees
22 Dec - 23 Dec
Royal Regency Hotel
Front of property
Amsterdam Hotel

Amsterdam Hotel

2.0 star property
Downtown Stamford
8.4 out of 10, Very Good, (1740)
"The service the breakfast was great"
United States
Nilsa
Amsterdam Hotel
Exterior
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

2.5 star property
Danbury
9.2 out of 10, Wonderful, (288)
"The room was great, very clean. Bed was excellent!"
United States
Michael
The price is SAR 417
SAR 480 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG
View from property
Inn on the Hudson

Inn on the Hudson

2.0 star property
Peekskill
6.8 out of 10, (1007)
"Always a pleasant place "
United States
Abner
The price is SAR 334
SAR 382 total
includes taxes & fees
7 Dec - 8 Dec
Inn on the Hudson
Standard Room, 2 Queen Beds, Accessible (ADA) | Desk, laptop workspace, blackout drapes, iron/ironing board
West Point Motel

West Point Motel

2.5 star property
Highland Falls
8.6 out of 10, Excellent, (656)
"GREAT STAFF NICE CLEAN ROOMS AND PROPERTY"
United States
Gregory
The price is SAR 375
SAR 424 total
includes taxes & fees
15 Dec - 16 Dec
West Point Motel
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.
View all properties

White Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ossining Hotel Reviews

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

10/10 Excellent
"From the front desk staff to the room, and ease of getting around, everything met our needs for our stay at your facility. Many thanks!"
Kathy 2-night trip
Posted 8 hours ago
Baymont by Wyndham White Plains - Elmsford

Frequently asked questions

What can I expect from a resort vacation in Ossining?
Longing for a relaxing escape? Treat yourself to all the comforts of a resort, where you can find everything you want for your trip from tasty food and drink options to activities and entertainment. Browse the resorts in the area and discover the right one for you, whether you envision yourself kicking back in a suite with stunning views or hitting the golf course for an afternoon game.
What's a top resort in Ossining?
Our highest-rated resort near Ossining: CAM BLISS RETREAT, Only room for one🌹❤️. - 15.3 mi (24.6 km) from Ossining. Access to 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 Rockland Bakery for some family fun. Sing Sing Correctional Facility and Sing Sing Prison Museum 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.