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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured B&B in Ossining

Cromwell Manor Inn
Exterior

Cromwell Manor Inn

3.5 star property
9.4 out of 10, Exceptional, (71)
"Very gracious innkeepers; great breakfast in a beautiful setting."
The price is AU$399
includes taxes & fees
24 Aug - 25 Aug
Cromwell Manor Inn
Stanton House Inn
Reception

Stanton House Inn

3.5 star property
9.6 out of 10, Exceptional, (151)
"Excellent staff and the pool is awesome. "
Stanton House Inn
West Lane Inn
Terrace/patio

West Lane Inn

3.5 star property
9.8 out of 10, Exceptional, (52)
"Wonderful inn with great breakfast, very safe, wonderful new bathrooms, comfortable clean beds with excellebt dining options nearby."
The price is AU$661
includes taxes & fees
18 Aug - 19 Aug
West Lane Inn
Charming Grand View/Lake Loft in Brewster with WiFi, AC
Interior

Charming Grand View/Lake Loft in Brewster with WiFi, AC

10.0 out of 10, Exceptional, (7)
"Great location - quiet and private. Long bike rides each day and was able to come back to a great shower, and comfortable, relaxed exterior and interior environment. Slept very well."
Charming Grand View/Lake Loft in Brewster with WiFi, AC
Honey Maple Grove BnB
42-inch TV with digital channels, heated floors

Honey Maple Grove BnB

4.0 star property
9.2 out of 10, Wonderful, (5)
"Charming and quiet…. perfect bed and breakfast!"
Honey Maple Grove BnB
The Kittle House Inn
Free daily continental breakfast

The Kittle House Inn

3.5 star property
8.2 out of 10, Very good, (411)
"Beautiful place to stay with a great staff "
The Kittle House Inn
Cozy Homeva Battle Hill WP
Exterior

Cozy Homeva Battle Hill WP

3.0 star property
Cozy Homeva Battle Hill WP
Cozy Homeva Kensico WP
Front of property

Cozy Homeva Kensico WP

3.0 star property
10.0 out of 10, Exceptional, (1)
"Eva & her son Matthew were very friendly & accommodating."
Cozy Homeva Kensico WP
Cozy Homeva Chatterton WP
Porch

Cozy Homeva Chatterton WP

3.0 star property
Cozy Homeva Chatterton WP
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

La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

10/10 Excellent
"Bueno"
Adam 1-night trip
Posted 14 hours ago
La Quinta Inn & Suites by Wyndham Stamford / New York City

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 might be the perfect option for your holiday. While you're here, you can get to know Ossining by exploring its natural beauty—consider stopping at 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 meet guests from other places and hearty breakfasts, B&Bs offer a unique setting.
What are the best B&Bs in Ossining?
Here are some B&Bs in the area: Stanton House Inn: 20 rooms. 15.1 mi (24.3 km) from the city centre. Enjoy the snack bar/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 decor.
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 temperature of 22°C, while the coldest months are January and February, with an average of 1°C. Average annual precipitation for Ossining is 1302 mm.
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 should put Sing Sing Correctional Facility and Thomas J. Watson Research Center on your list if you want to see more of the area.
How can I get to and around Ossining?
Mapping out your trip in and around Ossining is easy with these transportation options. Fly into White Plains, NY (HPN-Westchester County), which is located 10.5 mi (16.8 km) away from the city centre. You can also search 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.