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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

B&B in Ossining

Cromwell Manor Inn
Exterior

Cromwell Manor Inn

3.5 star property
9.4 out of 10, Exceptional, (61)
"It is set in a quiet small community. The grounds are beautiful and restful. There is a lovely patio. It is a haven for escape from the busy world. "
The price is AEDĀ 748
AEDĀ 884 total
includes taxes & fees
22 Jun - 23 Jun
Cromwell Manor Inn
Stanton House Inn
Reception

Stanton House Inn

3.5 star property
9.6 out of 10, Exceptional, (141)
"Quaint New England Inn experience "
Stanton House Inn
West Lane Inn
Terrace/patio

West Lane Inn

3.5 star property
9.8 out of 10, Exceptional, (48)
"Wonderful inn with great breakfast, very safe, wonderful new bathrooms, comfortable clean beds with excellebt dining options nearby."
The price is AEDĀ 1,373
AEDĀ 1,578 total
includes taxes & fees
17 Jun - 18 Jun
West Lane 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)
"Charming and quietā€¦. perfect bed and breakfast!"
Honey Maple Grove BnB
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, (2)
"I loved this place. I only wish I had more time to spend there.Orestes but so lovely to speak to and obviously takes great pride and sharing this air b and b. and the breakfastā€¦ Super delicious. I hope to be back."
Charming Grand View/Lake Loft in Brewster with WiFi, AC
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 Chatterton WP
Porch

Cozy Homeva Chatterton WP

3.0 star property
Cozy Homeva Chatterton WP
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
Cosy get away stay at Joanas
1 bedroom, iron/ironing board, WiFi, bed sheets

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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Frequently asked questions

Searching for B&Bs in Ossining?
If youā€™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 youā€™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: 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 dƩcor.
When should I book my B&B in Ossining?
When youā€™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 71Ā°F, while the coldest months are January and February with an average of 34Ā°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 youā€™re hoping to see some of the areaā€™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 youā€™d like to venture out around the area, you may want a rental car for your journey.