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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Ossining bed & breakfast

A brick building with a covered patio area featuring outdoor seating and string lights.

1. Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.4 out of 10, Exceptional, (112 reviews)
"This property was beautiful!! Everything was clean and thoughtful, breakfast was homemade, with options from the staff. Staff were lovely, so friendly. Roy, the golden retriever was a cutie!! :)"
United States
Alice
The price is AED 1,142
AED 1,349 total
includes taxes & fees
9 Nov - 10 Nov
Cromwell Manor Inn
A large, white, two-story house with a wrap-around porch, surrounded by a well-maintained lawn and trees.

2. West Lane Inn

West Lane Inn
3.5 star property
Ridgefield
9.8 out of 10, Exceptional, (59 reviews)
"Great place to stay!"
United States
Susan
The price is AED 1,373
AED 1,579 total
includes taxes & fees
9 Nov - 10 Nov
West Lane Inn
A spacious room with a grand piano, wooden ceiling beams, and a cozy seating area with chairs and a sofa.

3. Loft Suite with Private Bathroom at Storm King Lodge

Loft Suite with Private Bathroom at Storm King Lodge
New Windsor
The price is AED 1,267
AED 1,552 total
includes taxes & fees
9 Nov - 10 Nov
Loft Suite with Private Bathroom at Storm King Lodge
A two-story house with a front porch, a stone chimney, and a well-maintained lawn.

4. Twin Bedroom with Private Bathroom at Storm King Lodge

Twin Bedroom with Private Bathroom at Storm King Lodge
New Windsor
The price is AED 1,056
AED 1,257 total
includes taxes & fees
9 Nov - 10 Nov
Twin Bedroom with Private Bathroom at Storm King Lodge
A two-story house with a front porch, a stone chimney, and a well-maintained lawn.

5. Loft Room with Private Bathroom at Storm King Lodge

Loft Room with Private Bathroom at Storm King Lodge
New Windsor
The price is AED 1,056
AED 1,291 total
includes taxes & fees
9 Nov - 10 Nov
Loft Room with Private Bathroom at Storm King Lodge
A wooden-paneled room with a bed, a chair, a dresser, and a window with curtains.

6. Pine Suite with Private Bathroom at Storm King Lodge

Pine Suite with Private Bathroom at Storm King Lodge
New Windsor
The price is AED 1,267
AED 1,552 total
includes taxes & fees
9 Nov - 10 Nov
Pine Suite with Private Bathroom at Storm King Lodge
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.
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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 wooden bridge over a lake with a sign reading "BERGMANN BOARDWALK".

Frequently Asked Questions

Searching for B&Bs in Ossining?

If you're looking for something a little more offbeat than your standard hotel, a bed and breakfast could be a great option for your trip. While you're here, you can get to know Ossining by exploring its natural beauty. Consider a stop by Louis Engel Waterfront Park and Teatown Lake Reservation.

How do you know if a B&B is the best choice for your stay?

With attentive service, opportunities to mingle with other guests, and top-rated breakfasts, B&Bs offer a unique setting.

What are the best B&Bs in Ossining?

Here are some B&Bs in the area: Adorable 2-bedroom bed & breakfast in fantastic Ossining location: 0.2 mi (0.3 km) from the heart of Ossining.Stanton House Inn: 20 rooms. 15.1 mi (24.3 km) from the downtown core. Enjoy the deli and outdoor pool. Honey Maple Grove BnB: 3 rooms. Located 13 mi (21 km) from the core of Ossining. Enjoy the free full breakfast and unique décor.

When should I book my B&B in Ossining?

When you're planning your escape to Ossining, year-round temperatures and rainfall may be important factors to consider. 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 is there to do in Ossining?

Spend some time exploring Louis Engel Waterfront Park and Teatown Lake Reservation if you're hoping to see some of the area's natural features. You might put Sing Sing Prison Museum and Ossining Historical Society on your list if you want to see more of the area.

How can I get to and around Ossining?

Planning your excursions in and around Ossining is easier with these transportation options. Fly into Westchester County Airport (HPN), which is located 10.5 mi (16.8 km) from the city center. Otherwise, look for flights into Teterboro, NJ (TEB), which is 23.9 mi (38.5 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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