Search B&B in New Windsor

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for New Windsor bed & breakfast

Dining
Hollerstown Hill Bed and Breakfast

Hollerstown Hill Bed and Breakfast

Hollerstown Hill Bed and Breakfast
3.5 star property
Frederick
9.6 out of 10, Exceptional, (93)
"Quaint property in quiet neighborhood convenient for Frederick town center. Hosts are friendly and welcoming. Comfortable room with nice breakfast. Enjoyable relaxing stay."
United States
Eric
The price is AED 781
AED 828 total
includes taxes & fees
1 Jan - 2 January 2026
Hollerstown Hill Bed and Breakfast
Exterior
Inn at Mary's Land Farm

Inn at Mary's Land Farm

Inn at Mary's Land Farm
3.0 star property
Clarksville
10.0 out of 10, Exceptional, (23)
"Clean, beautiful surroundings! Excellent staff and breakfast!"
United States
John
The price is AED 764
AED 863 total
includes taxes & fees
14 Dec - 15 Dec
Inn at Mary's Land Farm
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 New Windsor Hotel Reviews

Hampton Inn & Suites Frederick-Fort Detrick

Hampton Inn & Suites Frederick-Fort Detrick

10/10 Excellent
"Room was nice and clean. Staff was amazing and breakfast and coffee was great!"
Shawn 2-night trip
Posted 1 day ago
Hampton Inn & Suites Frederick-Fort Detrick

Frequently asked questions

Searching for B&Bs in New Windsor?
If you're looking for something a little more offbeat than your standard hotel experience, a stay at a bed and breakfast could be a great option for your trip. When you want to explore some of the destination's attractions, Old Westminster Winery is worth a visit.
Why consider a B&B over a traditional hotel room?
With attentive service, opportunities to meet other guests, and top-rated breakfasts, B&Bs offer a one-of-a-kind setting.
What are the top B&Bs in New Windsor?
Here are some well-liked B&Bs in the area: Baladerry Inn LP: 5 rooms. Situated 18.6 mi (30 km) from the heart of New Windsor. Enjoy the local cuisine breakfast and private yard. Battlefield Bed & Breakfast Inn: 12 rooms. 18 mi (28.9 km) from the heart of downtown. Enjoy the free full breakfast and designer toiletries. Lightner Farmhouse B&B: 6 rooms. Located 17.7 mi (28.5 km) from the core of New Windsor. Enjoy the free full breakfast and unique décor.
When should I stay at a B&B in New Windsor?
When you're dreaming of a escape to New Windsor, be sure to take into account the year-round temperatures. 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 36°F. Average annual precipitation for New Windsor is 53 inches.
What is there to do in New Windsor?
When you want to explore some things to do in New Windsor, consider a visit to Old Westminster Winery. You might also consider a trip to sites like Elk Run Vineyards or Carroll County Farm Museum if you have time to see more of the area.
How can I get to and around New Windsor?
Planning your excursions in and around New Windsor is easier with these transportation options. Fly into Gaithersburg, MD (GAI-Montgomery County Airpark), which is located 26 mi (41.9 km) away from the city center. You can also search for flights into Baltimore Washington Intl. Airport (BWI), which is 34.3 mi (55.2 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.