A wooden boardwalk winding through a forest with autumn foliage.

Find a Bed and Breakfast in Ossining from CA $481

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

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 CA $436
CA $515 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $524
CA $602 total
includes taxes & fees
Nov 9 - Nov 10
West Lane Inn
A room with a wooden floor, a dresser, two leather armchairs, a small table with a clock, a lamp, and a framed picture on the wall.

3. Loft Suite with Private Bathroom at Storm King Lodge

Loft Suite with Private Bathroom at Storm King Lodge
New Windsor
The price is CA $482
CA $594 total
includes taxes & fees
Dec 7 - Dec 8
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 CA $402
CA $481 total
includes taxes & fees
Dec 7 - Dec 8
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 CA $402
CA $495 total
includes taxes & fees
Dec 7 - Dec 8
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 CA $482
CA $594 total
includes taxes & fees
Dec 7 - Dec 8
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.
View all properties
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

West Gate Inn Nyack

West Gate Inn Nyack

10/10 Excellent
"Everything was good, but the wifi was not that great in the room"
Lakyisha 1-night trip
Posted 4 hours ago
West Gate Inn Nyack

Find out more about Ossining

Ossining B&B information

Number of reviews
59
Accommodation
11 B&B
Lowest Price
CA $481
Highest Price
CA $602

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.

Explore a world of travel with Expedia