New Windsor, MD

Travel Guide

Visit New Windsor

Hyatt Place Baltimore/Owings Mills

4730 Painters Mill Rd Owings Mills MD

$98 nightly

$113 total

Sep 27 - Sep 28

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! (1,389 reviews)

"clean"

Reviewed on Sep 19, 2026

Inn at Cemetery Hill

613 Baltimore St Gettysburg PA

$155 nightly

$172 total

Sep 20 - Sep 21

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! (1,076 reviews)

"Stayed for 1 night and thank God it was only a night. Pretty nasty. Sheets were stained. Trash was not removed. Bathroom toilet was dirty (see the images for yourself). Still can’t believe all the positive ratings and the price. How is it $165/night?! This was a motel quality and should be priced ..."

Reviewed on Sep 18, 2026

Best Western Historic Frederick

420 Prospect Blvd Frederick MD

$94 nightly

$104 total

Oct 8 - Oct 9

Total with taxes and fees

Stay at this hotel in Frederick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...

8/10 Very Good! (1,004 reviews)

"The room I eventually got on the second floor was great. The room I originally had on the first floor smelled very musty and the smell did not go away after leaving the AC on while out for dinner. However, the front desk was great about changing my room to the second floor. Be aware that there is ..."

Reviewed on Sep 18, 2026

See all 338 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.

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

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 ...

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! (140 reviews)

"Would not stay here again.Unfortunately, I cannot recommend this VRBO for several reasons.The mirror fell off the bathroom wall while I was just washing my hands. I was lucky to have caught before it hit my face. Told the owner and he never apologized. Just said to stick it in the hall.There are ..."

Reviewed on Sep 18, 2026

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.

Check New Windsor hotel availability

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.