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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

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

Stanton House Inn
Reception

Stanton House Inn

3.5 star property
9.6 out of 10, Exceptional, (136)
"Beautiful old mansion, lovely staff "
Stanton House Inn
Cromwell Manor Inn
Exterior

Cromwell Manor Inn

3.5 star property
9.4 out of 10, Exceptional, (56)
"It was a beautiful stay, had everything you could think of for fun and convience, and the staff is very friendly. "
The price is AED 882
AED 997 total
includes taxes & fees
29 Mar - 30 Mar
Cromwell Manor Inn
West Lane Inn
Terrace/patio

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
30 Mar - 31 Mar
West Lane 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
Honey Maple Grove BnB
42-inch TV with digital channels, heated floors

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
Penthouse Suite At Cozy Homeva | Desk, laptop workspace, blackout drapes, iron/ironing board

Cozy Homeva Battle Hill WP

3.0 star property
Cozy Homeva Battle Hill 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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Other property types in Ossining

Global Luxury Suites White Plains
Reception

Global Luxury Suites White Plains

3.5 star property
6.6 out of 10, (30)
"Great location, friendly people, great apartment "
Global Luxury Suites White Plains
Luxury Apartments by Hyatus at The Asher
Lounge

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (15)
"The apartment was amazing. It was spacious, clean, incredibly comfy bed (although it made early mornings a problem!). The check in process was really easy. I also love the fact there is a huge washer and dryer so was able to do some washing mid-stay and not have to fill my suitcase up too much. The Gym was great and not too busy so was able to use the equipment I wanted to. I had a question one evening and emailed Hyatus expecting an answer the next day and they came back with a very helpful...
Luxury Apartments by Hyatus at The Asher
Stamford Suites
Exterior

Stamford Suites

3.0 star property
6.6 out of 10, (152)
"Room was very spacious "
The price is AED 582
AED 670 total
includes taxes & fees
24 Apr - 25 Apr
Stamford Suites
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 Louis Engel Waterfront 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 area: Stanton House Inn: 20 rooms. 15.1 mi (24.3 km) from the downtown core. Enjoy the deli and outdoor pool. Crabtree’s Kittle House Restaurant & Inn: 14 rooms. 6.3 mi (10.1 km) from the heart of downtown. Enjoy the bar/lounge and onsite dining. 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 Louis Engel Waterfront Park if you’re hoping to see some of the area’s natural features. You might put Sing Sing Prison Museum and Sing Sing Correctional Facility 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.