Western Maryland Holidays

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Our guide on where to stay in Western Maryland

Find the best Western Maryland areas and neighborhoods for the activities you enjoy most. Learn more about Western Maryland
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The Woods

If you're spending some time in The Woods, The Woods Resort Mountain View Course and Sleepy Creek Wildlife Management Area are top sights worth seeing.

Find hotels in The Woods

Western Maryland Holiday

Our pick of the best Western Maryland Hotel Deals

Rocky Gap Casino & Resort

Rocky Gap Casino & Resort

3 out of 5
16701 Lakeview Road NE, Cumberland, MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,356 reviews)
Everything was perfect , highly recommended

Reviewed on 3 Nov 2025

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Rocky Gap Casino & Resort
Ramada by Wyndham Cumberland Downtown

Ramada by Wyndham Cumberland Downtown

3 out of 5
100 South George Street, Cumberland, MD
Fully refundableReserve now, pay when you stay
The price is NZ$154 per night from 5 Nov to 6 Nov
NZ$154
5 Nov - 6 Nov
includes taxes & fees
6.8/10 (1,033 reviews)
Clean and friendly

Reviewed on 2 Nov 2025

Ramada by Wyndham Cumberland Downtown
Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

3 out of 5
5579 Spectrum Dr, Frederick, MD
Fully refundable
The price is NZ$152 per night from 9 Nov to 10 Nov
NZ$152
9 Nov - 10 Nov
includes taxes & fees
8.2/10 Very Good! (1,185 reviews)
Prefer healthier choices.

Reviewed on 30 Oct 2025

Country Inn & Suites by Radisson, Frederick, MD
See all 3,428 properties in Western Maryland
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.

Discover the most popular places to visit in Western Maryland

Antietam National Battlefield

Antietam National Battlefield

You can find out about the history of Sharpsburg with a visit to Antietam National Battlefield. Stroll along the riverfront or seek out the hiking trails.

Antietam National Battlefield
Downtown Cumberland Historic District

Downtown Cumberland Historic District

Find out about the history of Cumberland when you take a trip to Downtown Cumberland Historic District. Discover the area's mountain views and casinos.

Downtown Cumberland Historic District

What to do in Western Maryland

Evening view of the roof top deck on the Spirit of Baltimore cruise vessel

Spirit of Baltimore Signature Buffet Dinner Cruise with Live DJ & Bars

NZ$239
per adult
84% of travellers recommend
Spirit of Baltimore Signature Buffet Dinner Cruise with Live DJ & Bars
Glow in the Dark Splatter Paint Experience

Glow in the Dark Splatter Paint Experience

NZ$70
per adult
78% of travellers recommend
Glow in the Dark Splatter Paint Experience
Join us for a haunting experience!

The Original Fells Point Ghost Walk by Baltimore Ghost Tours

NZ$45
per adult
100% of travellers recommend
The Original Fells Point Ghost Walk by Baltimore Ghost Tours
See all activities in Western Maryland

Frequently asked questions

Can I cancel my flight booking to Western Maryland due to COVID-19?
Our Customer Service Portal is where you can find information about cancelling or changing your flight due to COVID-19. Before booking, it's wise to look over the terms and conditions of your chosen airline too.
What's the best way to find cheap flights to Western Maryland that have flexible change policies?
Search for your bargain flights to Western Maryland, then check the "No change fee" box directly under the "Flexible change policies" filter. It really is that simple. We know that things can change and flexibility is essential, so book with confidence with Expedia.
What are some of the general tips for travellers to Western Maryland during the COVID-19 outbreak?
If it's your first time travelling during the COVID-19 outbreak, you'll no doubt notice a few more restrictions and standards in place. Take note of these tips and make your trip to Western Maryland a smooth one:
  • Before committing to anything, see if any travel restrictions or bans apply — in both your destination and origin. Keep informed with the latest updates by checking government and travel websites.
  • Wear a face mask even during airport screening. A TSA officer will ask you to adjust your mask for ID purposes.
  • Rather than handing a TSA officer your boarding pass, position it straight on the scanner yourself. After that, hold it up for inspection.
  • You're permitted to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on luggage. You'll have to remove it for screening.
  • Place any personal items (phone, wallet and keys) in your carry-on instead of a bin to minimize handling during screening.
  • Transport all food items in a clear plastic bag and also place them in a screening bin. Separating food from your carry-on makes it less likely that a TSA officer will need to touch and open your bag for inspection.

Which airlines fly to Western Maryland?
Southwest Airlines offers flights into or near Western Maryland, including 5336 that travel to Baltimore Washington Intl. Thurgood Marshall Airport (BWI) each month. Work out your holiday dates and then lock in your seat early for the best deal.
How can I find cheap tickets to Western Maryland?
An excellent strategy for scoring cheap fares is to be flexible with your travel dates. Start by searching for your flight to Western Maryland, then click on the "flexible dates" link for a list of prices for nearby days. Another useful tip? Book well ahead of time. For an idea of fares, was the best price for a flight to Western Maryland in the last seven days.
How much is a flight to Western Maryland?
You could have purchased a return flight to Western Maryland from anywhere between and in the last seven days. For one-way journeys leaving from (), the lowest price during this time was just .
What are the most popular airports to fly into in Western Maryland?
Fly into Baltimore Washington Intl. Thurgood Marshall Airport (BWI) and enjoy everything that Western Maryland has to offer. As the region's primary entry point, approximately 7430 flights land here each month.
When is the cheapest time to fly to Western Maryland?
If you can be flexible with what date you jet off to Western Maryland, try to leave earlier in the week. The most affordable day to take off is generally Tuesday, closely followed by Monday. Saturday is typically the costliest day, with lots of holiday makers choosing to take off on the weekend.
How much is a plane ticket to Western Maryland?
In the last seven days, seats ranged between and . Check out our amazing deals to Western Maryland, make a booking and then start packing your things!
Which airlines with flights to Western Maryland employ COVID-19 cleanliness policies?
In an effort to reduce contact between travellers and cabin crew during the ongoing COVID-19 pandemic, most airlines have taken social distancing and other measures to the skies. Just a handful of these are:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.