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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 9 B&B in Ossining with updated reviews, rates, and availability.

Stanton House Inn
Lobby sitting area

Stanton House Inn

3.5 star property
9.6 out of 10, Exceptional, (135)
"Friendly and respectful staff. Easy access. Clean and quiet. Very friendly environment. One of the best stays ever. "
Stanton House Inn
Cromwell Manor Inn
Reception

Cromwell Manor Inn

3.5 star property
9.4 out of 10, Exceptional, (55)
"It was a beautiful stay, had everything you could think of for fun and convience, and the staff is very friendly. "
Cromwell Manor Inn
Crabtree's Kittle House Restaurant & Inn
Property entrance

Crabtree's Kittle House Restaurant & Inn

3.5 star property
8.2 out of 10, Very Good, (411)
"If rustic charm is on your bucket list, the Kittle House is brimming it….older floorboards, wooden beams, and a copper ceiling in the taproom. There are modern amenities alongside older fixtures….that plumbing (3/4”?) provides a powerful shower! We stayed during the holidays, and the inn was decorated beautifully. Continental breakfast included. This hotel services an area in Westchester that has few options for lodgings. Fortunately, this inn is a wonderful option."
Crabtree's Kittle House Restaurant & Inn
West Lane Inn
Exterior

West Lane Inn

3.5 star property
9.8 out of 10, Exceptional, (43)
"Great place to stay!"
The price is AED 1,263
AED 1,452 total
includes taxes & fees
24 Feb - 25 Feb
West Lane Inn
Honey Maple Grove BnB
Terrace/patio

Honey Maple Grove BnB

4.0 star property
9.6 out of 10, Exceptional, (4)
"Abbott the owner and host was very accomodating. Everything was clean and well maintained. Location is perfect. Will stay there whenever we are in the area"
Honey Maple Grove BnB
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 Battle Hill WP
Front of property

Cozy Homeva Battle Hill WP

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

Cozy Homeva Chatterton WP

3.0 star property
Cozy Homeva Chatterton WP
Cosy get away stay at Joanas
Room

Cosy get away stay at Joanas

Cosy get away stay at Joanas
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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Other property types in Ossining

Stamford Suites
Exterior

Stamford Suites

3.0 star property
5.6 out of 10, (23)
"Room was very spacious "
The price is AED 621
AED 714 total
includes taxes & fees
8 Mar - 9 Mar
Stamford Suites
Global Luxury Suites White Plains
Room

Global Luxury Suites White Plains

3.5 star property
7.0 out of 10, Good, (28)
"I was very impressed with this "hotel". It is more of an AirBB as your unit is an apartment in an apartment building with permant residents. It comes nicely furnished, including basic kitchen essentials (like service for four, pots and pans, coffee maker, etc). All of the amenities are modern, and the in-unit washer dryer is a huge plus. I also really appreciated some of the welcome gifts, including some coffee/tea, laundry detergent, and your basic hygiene essentials. Property communicates...
Global Luxury Suites White Plains
Chic, Modern & Cozy~Close to NYC Free Parking!
Exterior

Chic, Modern & Cozy~Close to NYC Free Parking!

9.6 out of 10, Exceptional, (4)
"The location was perfect for my trip to the area. Loved the easy access and parking."
Chic, Modern & Cozy~Close to NYC Free Parking!
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.

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 Teatown Lake Reservation and Snowden Avenue Park.
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 surrounding area: Stanton House Inn: 20 rooms. 15.1 mi (24.3 km) from the heart of Ossining. Enjoy the deli and outdoor pool. Crabtree’s Kittle House Restaurant & Inn: 14 rooms. Situated 6.3 mi (10.1 km) from the heart of Ossining. Enjoy the onsite dining and bar/lounge. 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 Teatown Lake Reservation and Snowden Avenue Park if you’re hoping to see some of the area’s natural features. You might 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?
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.