Middletown Holidays from AU$1,545
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Your Middletown Holiday
Say bye-bye to the worries of planning and hello to a Middletown holiday package. With the finer details organised before you leave, you can focus on discovering the best of this city, starting with Downtown Frederick, which is great for cafes, history and bars and pubs. Any trip to Middletown needs a well-thought-out itinerary. Fill yours with major attractions like Musket Ridge Golf Course, Maryland National Golf Club and Washington Monument State Park. Expedia is here to help you escape your daily routine. Tailor your holiday to Middletown to suit your style of travel, whatever that may look like.
The Latest Middletown Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Eurostars Saint Gregory Dupont Circle Georgetown
Downtown Washington D.C.
AU$1,545
per person
22 Dec - 29 Dec
found 5 hours ago
Return direct flight included
London (LON) to Baltimore (BWI)
8.6/10 Excellent! (1,012 reviews)
This hotel needs overall updating. The staff was helpful and friendly, but the HVAC had significant issues. I was hot all night long and there was no way to control the temperature in the room. Also, it made a very loud noise several times a night that woke me up in a way that terrified me. So weird. It sounded like someone trying to break into the room...my adrenaline would go sky high. So hard to go back to sleep after that. I will not be back. Also, I had issues with my TV and had to switch rooms late at night after I had already gotten in bed.
Reviewed on 15 Oct 2026
The Potomac Hotel, Autograph Collection
Southwest
AU$3,084
per person
22 Dec - 29 Dec
found 4 hours ago
Return direct flight included
London (LON) to Baltimore (BWI)
9.4/10 Exceptional! (1,089 reviews)
Clean, convenient to many walkable places and easy to get a taxi or Uber if needed.
Reviewed on 13 Oct 2026
Riggs Washington DC
Downtown Washington D.C.
AU$3,420
per person
22 Dec - 29 Dec
found 4 hours ago
Return direct flight included
London (LON) to Baltimore (BWI)
9.4/10 Exceptional! (1,415 reviews)
I want to love this property because staff are amazing (although everyone appears to be younger and I’m sensitive to age discrimination) and location really works for me but there are some obvious flaws… the large awkward inner bathroom door being the first, a floating column in the room being another, lighting being yet another (bathroom lighting is awful… too bright, no nightlight sensor), impossible to read bodycare labels, and poorly operable hairdryer and clothing steamer. Bed and linens are good quality, appreciate the complimentary bottled water, and loved the breakfast options and drinks menu (but quality of mixed drinks was uneven). This was my second time here and service has notched up but some things are not keeping up with recent trends and comfort. Still a better than average experience.
Reviewed on 14 Oct 2026
Middletown Holiday
Middletown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Hagerstown Regional Airport (HGR) |
Population | 4,500 |
Max Temp Winter | 4ºC |
Max Temp Summer | 29ºC |
Top Sights | Orchid Cellar Winery, Musket Ridge Golf Course and Maryland National Golf Club |
Our pick of the best Middletown Hotel Deals
Country Inn & Suites by Radisson, Hagerstown, MD
17612 Valley Mall Rd Hagerstown MD
Fully refundable
AU$135
8 Nov - 9 Nov
includes taxes & fees
8.6/10 Excellent! (1,335 reviews)
"Great Stay"
Reviewed on 14 Oct 2026
Best Western Historic Frederick
420 Prospect Blvd Frederick MD
Fully refundableReserve now, pay when you stay
AU$123
25 Oct - 26 Oct
includes taxes & fees
Quality Inn Harpers Ferry - Charles Town
25 Union St Harpers Ferry WV
Fully refundable
AU$144
29 Oct - 30 Oct
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"Nice room for the price. Very good breakfast."
Reviewed on 15 Oct 2026
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
Designed by Arthur Hills, this par-71 course features dramatic elevation changes and views of the Catoctin Mountains. Enjoy the challenging fairways and relax at the full-service clubhouse after your round.
Orchid Cellar Winery
9.0/10 (2 reviews)
Orchid Cellar crafts diverse meads in a hand-built log cabin tasting room with mountain views. Enjoy a flight on the wrap-around deck while watching resident bees and chickens or roasting s'mores by the fire pit.
Willow Oaks Craft Cider and Wine
Maryland's first certified organic farm offers barrel-aged craft ciders and port-style wines from its 35-acre orchard. Savour a tasting on the deck overlooking the apple trees while browsing local art in the gallery.
Frequently asked questions
How much does a Middletown holiday package cost?
You can snap up a holiday package to this destination from AU$1,545 on Expedia. However, how much your holiday to Middletown costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Middletown?
The off-season is the best time to head to Middletown if you're on a budget. Another tip for finding cheap Middletown holiday packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Middletown?
With a well-organised schedule, you can easily visit the most popular Middletown sights in a handful of days. But if you'd like to discover hidden gems or go on day trips, consider booking your Middletown holiday for longer.
How to find the best Middletown package deals?
Use Expedia's handy filters to help you find some great Middletown package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Middletown package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your holiday package as soon as possible.
Is it cheaper to book a Middletown holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component individually. And you'll still get the flexibility to create a personalised Middletown holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Middletown?
If you've got your Middletown holiday dates confirmed, book as soon as you can to grab some incredible deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Middletown?
- Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Middletown.
- Plan your budget wisely: In addition to the price of your stay, you'll need to factor in other expenses too. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that could arise during your trip to Middletown.
- Work out your trip length: Consider how much time you'd like to spend discovering Middletown. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
- Combine your airfare and accommodation: Once you've nailed down your travel dates and duration, lock in the right Middletown holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
