Western Maryland Vacation Packages 2026 from $216

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Your Western Maryland Vacation

Travel on your own terms with a vacation package to Western Maryland. Whether you're going for the nature, history, culture, or something else, our package deals make travel planning a breeze. Begin your trip to Western Maryland with some time exploring Frederick visiting popular attractions like Francis Scott Key Mall and Frederick Fairgrounds. Hagerstown is another top city that draws crowds from near and far. Greenbrier State Park and Hagerstown Speedway are two of the leading places to see in this destination. From the instant you book your Western Maryland vacation to when you get back home, Expedia will take care of you every step of the way.

The Latest Western Maryland vacation packages

Price found within the past 48 hours. Click for updated prices.

Holiday Inn Columbia East-Jessup by IHG

Save 100% on your flight

$216

per person

Nov 14 - Nov 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

8.8/10 Excellent! (1,000 reviews)

Hotel Burg

Leesburg's Old and Historic District

Save 100% on your flight

$645

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Baltimore (BWI)

9.6/10 Exceptional! (128 reviews)

Phoenix Park Hotel

Northwest

Save 100% on your flight

$386

per person

Dec 30 - Jan 4

found 1 day ago

Roundtrip flight included

Miami (MIA) to Baltimore (BWI)

9.4/10 Exceptional! (2,166 reviews)

Thank you for the lovely stay!

Reviewed on Oct 13, 2026

Crowne Plaza Crystal City-Washington, D.C. by IHG

Crystal City

Save 100% on your flight

$384

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

8.2/10 Very Good! (1,014 reviews)

Beautiful hotel great area very helpful staff

Reviewed on Oct 15, 2026

citizenM Washington DC Georgetown

Northwest

Save 100% on your flight

$356

per person

Nov 22 - Nov 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9.2/10 Wonderful! (166 reviews)

Staff was helpful and place was clean, but there was a leak in my room under the shower. Rooms are really space efficient (small) and modern.

Reviewed on Oct 14, 2026

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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

A nighttime riverside walkway with a bridge, street lamps, and a building in the background.

Downtown Frederick

If you're spending some time in Downtown Frederick, National Museum of Civil War Medicine and Carroll Creek Linear Park are top sights worth seeing.

A river winding through a dense forest with a mountain in the background.

The Woods

If you're spending some time in The Woods, The Woods Resort Mountain View Course and The Woods Resort Stony Lick Course are top sights worth seeing.

A waterfall cascading over rocks into a clear pool.

Mountainside

Mountainside might not have many top sights, but Deep Creek Lake and Deep Creek Lake State Park are two attractions nearby that you can check out.

Waterfront Greens

While there might not be top attractions in Waterfront Greens, you can explore the larger area and discover places like Deep Creek Lake State Park and Thousand Acres Lakeside Golf Course.

Blakeslee

While there might not be top attractions in Blakeslee, you can explore the larger area and discover places like Deep Creek Lake and Deep Creek Lake State Park.

Stay near popular Western Maryland attractions

A lakeside view with boats, houses, and a grassy area.

Deep Creek Lake State Park

9.2/10 (259 reviews)

You can take time to visit Deep Creek Lake State Park during your travels to Swanton. While you're in the area, wander around the parks.

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A grassy field with a ski lift and trees in the background.

Wisp Resort

8.8/10 (237 reviews)

Hit the slopes in McHenry with a visit to Wisp Resort. Wander the riverfront in this family-friendly area.

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A waterfall cascading over a rocky cliff surrounded by lush greenery.

Swallow Falls State Park

9.8/10 (138 reviews)

You can take time to visit Swallow Falls State Park during your travels to Oakland. Stroll along the riverfront in this family-friendly area, or seek out the ski slopes.

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A train numbered 501 on tracks under a bridge.

Downtown Cumberland Historic District

8.6/10 (424 reviews)

Find out about the history of Cumberland when you spend time at Downtown Cumberland Historic District. Discover the area's mountain views and casinos.

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A park with a gazebo, green trees, a paved path, and signs prohibiting beer and alcoholic beverages.

Berkeley Springs State Park

9.0/10 (202 reviews)

Soak in therapeutic waters at Roman baths and learn about the history of the spa at the park’s museum.

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Western Maryland Scenic Railroad

9.0/10 (224 reviews)

You can find out about the history of Cumberland with a visit to Western Maryland Scenic Railroad. Discover the area's mountain views and seek out the biking trails.

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Hagerstown Premium Outlets

8.2/10 (431 reviews)

During your trip to Hagerstown, you can do some window-shopping at Hagerstown Premium Outlets. While in this family-friendly area, you can savor the top-notch restaurants.

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What to do in Western Maryland

Baltimore's Historical Sightseeing Tour

$48

per adult

98% of travellers recommend

Glow in the Dark Splatter Paint Experience

$40

per adult

78% of travellers recommend

Baltimore: Fun Dumpling Making Class With a Local Chef

$75

per adult

See all activities in Western Maryland

Western Maryland Hotel Deals

Rocky Gap Casino & Resort

16701 Lakeview Road NE Cumberland MD

Fully refundableReserve now, pay when you stay

$140 nightly

$160 total

Nov 2 - Nov 3

Total with taxes and fees

9/10 Wonderful! (1,709 reviews)

"Hot tub not working entire 4 days."

Reviewed on Oct 15, 2026

Ramada by Wyndham Cumberland Downtown

100 South George Street Cumberland MD

Fully refundableReserve now, pay when you stay

$70 nightly

$80 total

Nov 15 - Nov 16

Total with taxes and fees

6.8/10 (1,006 reviews)

"Property provided a place to sleep but not much more. There is notbactual worker working the front desk, just a guy on a tablet talking to you from a screen from remote location. They have no type of helpfulness for guests. I had a party with six rooms and we asked if we could have early check in ..."

Reviewed on Oct 11, 2026

Country Inn & Suites by Radisson, Hagerstown, MD

17612 Valley Mall Rd Hagerstown MD

Fully refundable

$84 nightly

$94 total

Nov 8 - Nov 9

Total with taxes and fees

8.6/10 Excellent! (1,336 reviews)

"Great stay!"

Reviewed on Oct 15, 2026

See all 3,194 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.