New Windsor, MD

Travel Guide

Sunday Morning at Savannahs

Sunday Morning at Savannahs

4 out of 5
111 South Springdale Avenue, New Windsor New Windsor MD
$140 nightly
The price is $149 total per night from Oct 1 to Oct 2
$149 total
Oct 1 - Oct 2
Total with taxes and fees
Stay at this B&B in New Windsor. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Old Westminster Winery and Kate Wagner Fields are located ...
10/10 Exceptional! (1 review)
"Perfect getaway!"

Reviewed on Sep 27, 2026

Sunday Morning at Savannahs
Inn at Cemetery Hill

Inn at Cemetery Hill

2 out of 5
613 Baltimore St Gettysburg PA
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $209 total per night from Oct 1 to Oct 2
$209 total
Oct 1 - Oct 2
Total with taxes and fees
Stay at this hotel in Gettysburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (1,101 reviews)
"Always a nice stay."

Reviewed on Sep 30, 2026

Inn at Cemetery Hill
Hyatt Place Baltimore/Owings Mills

Hyatt Place Baltimore/Owings Mills

3 out of 5
4730 Painters Mill Rd Owings Mills MD
$98 nightly
The price is $113 total per night from Oct 7 to Oct 8
$113 total
Oct 7 - Oct 8
Total with taxes and fees
Book a stay at this business-friendly hotel in Owings Mills. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,399 reviews)
"Rooms are recently updated. Breakfast was just ok, have had better free hotel breakfasts."

Reviewed on Sep 30, 2026

Hyatt Place Baltimore/Owings Mills
See all 335 properties in New Windsor
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.
Countryside Cabin with Mountain Views near Surreybrooke Gardens

Countryside Cabin with Mountain Views near Surreybrooke Gardens

Middletown MD
Stay at this cabin in Middletown. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Maryland National Golf Club and Orchid Cellar Winery ...
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Battlefield Cottage - Located near the Heart of Gettysburg, PA

Battlefield Cottage - Located near the Heart of Gettysburg, PA

Gettysburg PA
Stay at this cottage in Gettysburg. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Gettysburg National Military Park and Gettysburg National ...
10/10 Exceptional! (2 reviews)
"We had a great time!!!!! The house is adorable!!! Clean and neat! We loved our stay!!!! Highly recommend! Communication with Jared was great!!"

Reviewed on Sep 7, 2026

Battlefield Cottage - Located near the Heart of Gettysburg, PA
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Frederick MD
Stay at this vacation home in Frederick. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions National Museum of Civil War Medicine ...
9.2/10 Wonderful! (141 reviews)
"I has very happy with the cleanliness and location of the property. Definitely love having parking directly behind the home. No doubt I will stay here again when coming back to Frederick Maryland...."

Reviewed on Sep 22, 2026

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
See all properties in New Windsor
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.

Stay near popular New Windsor attractions

Old Westminster Winery

6.8/10 (11 reviews)
You can enjoy a tasting or tour at Old Westminster Winery during your travels to New Windsor. While in this family-friendly area, you can enjoy the restaurants.
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Frequently asked questions

When is the best time to visit New Windsor?
The best time to visit New Windsor is from May through September, when the weather is generally pleasant for exploring. For fewer crowds and better value, the quieter months of November through February are a good option, offering a different experience with cooler, sometimes snowy, weather.
What cuisines can you find in New Windsor?
In New Windsor you can find Indian cuisine, with dishes like rich curries, fluffy naan bread, and flavorful biryani. Travelers can also enjoy Italian, Latin American (Mexican), and Asian options, including Chinese and Japanese. Additionally, there are European (Mediterranean) and North American flavors available.
Can I book a refundable hotel in New Windsor?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in New Windsor by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to New Windsor with Expedia?
Expedia makes it easier to plan your New Windsor trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in New Windsor?
The best choice depends on your travel style. Hotels in New Windsor can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my New Windsor trip on Expedia?
Once you've booked your New Windsor trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my New Windsor trip?
Expedia offers customer support before, during, and after your New Windsor trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to New Windsor?
If it's your first trip to New Windsor, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my New Windsor hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your New Windsor hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near New Windsor

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Mount Airy

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