Middletown, MD

Travel Guide

A stone tower with a staircase leading up to it.
A stone archway with inscriptions and statues, surrounded by grass and trees.
A stone tower with a flagpole, surrounded by trees and a cloudy sky.
A stone tower with a flagpole and an American flag.
Quality Inn Harpers Ferry - Charles Town

Quality Inn Harpers Ferry - Charles Town

2.5 out of 5
25 Union St Harpers Ferry WV
$89 nightly
The price is $99 total per night from Oct 26 to Oct 27
$99 total
Oct 26 - Oct 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Harpers Ferry. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (1,002 reviews)
"Stayed here one night for a biz trip and was very pleased with the experience!! Quiet, clean, and a very comfortable bed. Tons of outlets available which was great because I had to tech check some gear and charge a bunch of batteries. They had a breakfast area but we did not have anything. Looked ..."

Reviewed on Oct 1, 2026

Quality Inn Harpers Ferry - Charles Town
Best Western Historic Frederick

Best Western Historic Frederick

2.5 out of 5
420 Prospect Blvd Frederick MD
$77 nightly
The price is $86 total per night from Oct 12 to Oct 13
$86 total
Oct 12 - Oct 13
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 ...
Best Western Historic Frederick
Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown

3 out of 5
89 ALL STAR COURT Hagerstown MD
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $114 total per night from Oct 11 to Oct 12
$114 total
Oct 11 - Oct 12
Total with taxes and fees
Book a stay at this business-friendly hotel in Hagerstown. Enjoy free breakfast, a fitness center, and a 24-hour front desk. Our guests praise the breakfast ...
Fairfield Inn & Suites by Marriott Hagerstown
See all 837 properties in Middletown
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 ...
10/10 Exceptional! (159 reviews)
"Lovely place to stay. Very accommodating. I can only imagine how beautiful it is during the fall. A nice place to stay with your fur baby. We had to carry our little guy up and down stairs because he has never seen stairs before. lol! Very clean and the scones were delicious!"

Reviewed on Sep 30, 2026

Countryside Cabin with Mountain Views near Surreybrooke Gardens
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Middletown MD
Stay at this cabin in Middletown. Enjoy laundry facilities, an in-room coffeemaker, and in-room fireplaces. Popular attractions Orchid Cellar Winery and Willow ...
9.6/10 Exceptional! (116 reviews)
"We had a wonderful stay at the cabin. Everything looked exactly like the photos and the atmosphere was quaint, calm and relaxing. We were conveniently located to several restaurants and the area was lovely. Overall, we were very happy with our experience."

Reviewed on Jun 25, 2026

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

Harpers Ferry WV
Stay at this apartment in Harpers Ferry. Enjoy free WiFi, in-room fireplaces, and air conditioning. Popular attractions Harpers Ferry National Historical Park ...
9.2/10 Wonderful! (48 reviews)
"10/10 every time, We've stayed here twice now and you can’t beat the location. Super great host and wonderful experience."

Reviewed on Sep 20, 2026

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
See all properties in Middletown
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 Middletown attractions

Maryland National Golf Club

Enjoy a round of golf in Middletown at Maryland National Golf Club. Discover the coffeehouses and its festivals while you're in the area.
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Frequently asked questions

Is Middletown worth visiting?
Middletown is worth visiting for its standout attractions, such as the Maryland National Golf Club for golf enthusiasts and the Orchid Cellar Winery for wine tasting. Travelers can also enjoy diverse dining options, with a selection of Italian and Asian cuisine available.
When is the best time to visit Middletown?
The best time to visit Middletown is from May through September, when the weather is typically mild and pleasant. For fewer crowds and better value, the quieter months of November through February are a good option, offering a cooler experience for travelers.
What is Middletown known for?
Middletown is known for being home to the Maryland National Golf Club, offering a destination for golf enthusiasts. Travelers can also explore local producers like Orchid Cellar Winery and Willow Oaks Craft Cider and Wine, and find a strong Italian food culture throughout the city.
What is a good itinerary length for Middletown?
A good itinerary length for Middletown is two days to enjoy key highlights like the Maryland National Golf Club and a visit to Orchid Cellar Winery or Willow Oaks Craft Cider and Wine. An extended stay of three to four days allows you to experience all the attractions and explore the local Italian, Asian, and North American dining options.
What are the top things to do in and around Middletown?
Middletown offers a relaxing escape with golf and local beverage experiences:


How do I plan a trip to Middletown?
To plan your Middletown trip, search for places to stay and book flights in advance. Consider booking activities like a round at Maryland National Golf Club or a visit to Orchid Cellar Winery. A rental car will help you explore the area. Remember to pair any outdoor plans with indoor backups for weather flexibility.
What cuisines can you find in Middletown?
In Middletown, travelers can find New American cuisine, featuring dishes like gourmet burgers and creative small plates. Travelers also have diverse options including Italian favorites such as pasta and pizza, along with Asian selections like Chinese and Japanese, and Latin American dishes such as Mexican.
Can I book a refundable hotel in Middletown?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Middletown 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 Middletown with Expedia?
Expedia makes it easier to plan your Middletown 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 Middletown?
The best choice depends on your travel style. Hotels in Middletown 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 Middletown trip on Expedia?
Once you've booked your Middletown 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 Middletown trip?
Expedia offers customer support before, during, and after your Middletown 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 Middletown?
If it's your first trip to Middletown, 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 Middletown 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 Middletown hotel.

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

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