Western Maryland Vacation Packages 2026 from $402

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.

Arlo Washington DC

Northwest

$402

per person

Dec 18 - Dec 22

found 16 hours ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9.4/10 Exceptional! (2,000 reviews)

The stay was great!! Very clean, and room was awesome! Our only negative was we weren’t given a lot of explanation to how everything at the hotel “operates” upon check in, notably a quick rundown of the elevator and parking process. We were able to figure it out, but it’s a little nerve wracking when it’s busy check in times and you’re not sure of the process.

Reviewed on Sep 26, 2026

Hotel Hive

Northwest

Save 100% on your flight

$552

per person

Dec 9 - Dec 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9.4/10 Exceptional! (1,592 reviews)

Clean room. Great staff

Reviewed on Sep 26, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Downtown Washington D.C.

Save 100% on your flight

$514

per person

Nov 13 - Nov 16

found 3 hours ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

8.8/10 Excellent! (1,009 reviews)

Lyle Washington D.C.

Northwest

Save 100% on your flight

$523

per person

Dec 18 - Dec 22

found 16 hours ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9.4/10 Exceptional! (1,630 reviews)

We always stay here in W, great Hotel

Reviewed on Sep 26, 2026

Glover Park Hotel Georgetown

Northwest

Save 100% on your flight

$605

per person

Dec 9 - Dec 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

8.8/10 Excellent! (3,206 reviews)

Reviewed on Sep 26, 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, Carroll Creek Linear Park and Historical Society of Frederick County 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 Sleepy Creek Wildlife Management Area 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 Thousand Acres Lakeside Golf Course and Deep Creek Lake State Park.

Blakeslee

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

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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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 Ravens Football Game at M&T Bank Stadium

$314

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

$150 nightly

$171 total

Oct 25 - Oct 26

Total with taxes and fees

9/10 Wonderful! (1,700 reviews)

"Stayed for our sons wedding at the Lakeside Pavilion. Had a wonderful stay. Views were amazing and the weather was perfect. Highly recommend"

Reviewed on Sep 26, 2026

Best Western Historic Frederick

420 Prospect Blvd Frederick MD

Fully refundableReserve now, pay when you stay

$77 nightly

$85 total

Oct 4 - Oct 5

Total with taxes and fees

8/10 Very Good! (1,002 reviews)

"Traveling between Antietam and Gettysburg looking for place to stay. Options seemed limited and reviews on this hotel seemed"

Reviewed on Sep 24, 2026

Ramada by Wyndham Cumberland Downtown

100 South George Street Cumberland MD

Fully refundableReserve now, pay when you stay

$84 nightly

$96 total

Sep 29 - Sep 30

Total with taxes and fees

6.8/10 (1,009 reviews)

"The room was near and clean. The hotel itself however feels like it's dying a slow death. Only one elevator works, the ice machines don't work and the vending machines don't work and you can only get snacks from the counter with cash. The pool looks like it hasn't been used for quite a while. The ..."

Reviewed on Sep 25, 2026

See all 3,196 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.