A wooden boardwalk winding through a forest with autumn foliage.

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Check prices for these dates

Next weekend
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug
In one month
4 Sep - 6 Sep
In two months
2 Oct - 4 Oct

Our top choices for Ossining bed & breakfast

Exterior

1. West Lane Inn

West Lane Inn
3.5 star property
Ridgefield
9.8 out of 10, Exceptional, (54 reviews)
"Great place to stay!"
United States
Susan
The price is AED 1,373
AED 1,579 total
includes taxes & fees
10 Aug - 11 Aug
West Lane Inn
Terrace/patio

2. Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.4 out of 10, Exceptional, (107 reviews)
"The stay was wonderful. The personnel were very accommodating."
United States
Steven
The price is AED 1,348
AED 1,592 total
includes taxes & fees
20 Aug - 21 Aug
Cromwell Manor Inn
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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Top Ossining Hotel Reviews

Hyatt Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent
"I absolutely enjoyed my stay at the Hyatt Regency in old Greenwich. The staff was lovely, the hotel was extremely clean and well kept. 10/10"
Kimberly 3-night trip
Posted 4 hours ago
Hyatt Regency Greenwich

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 Depot Square 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 Depot Square and Teatown Lake Reservation if you're hoping to see some of the area's natural features. You might put Sing Sing Correctional Facility and Ossining Public Library 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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