Western Maryland Vacations from $235
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
InterContinental Washington D.C. - The Wharf by IHG
The Wharf
Save 100% on your flight
Price was $734, price is now $341 per person
$341
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
18.8/10 Exceptional! (1,005 reviews)
Everything was fantastic. Beautiful property.
Reviewed on Nov 10, 2025
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Save 100% on your flight
Price was $821, price is now $413 per person
$413
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
18/10 Exceptional! (1,084 reviews)
Room was spotless and comfortable and quiet. All staff were very friendly and helpful. Great location to walk to the Metro and restaurants and the White House!
Reviewed on Oct 28, 2025
Embassy Suites by Hilton Washington D.C. – Convention Center
Downtown Washington D.C.
Save 100% on your flight
Price was $963, price is now $520 per person
$520
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
18.4/10 Exceptional! (2,031 reviews)
This hotel was a great place to stay.
Reviewed on Nov 20, 2025
Hotel Ulysses, a Member of Design Hotels
Mount Vernon
Save 100% on your flight
Price was $402, price is now $235 per person
$235
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
18.4/10 Exceptional! (979 reviews)
Was clean, needs mini refrigerators
Reviewed on Nov 20, 2025
Don't see what you're looking for?
See all available trips from Chicago to Western Maryland
View all trips
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
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.
Discover the most popular places to visit in Western Maryland
Deep Creek Lake State Park
4.5/5(58 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.
Antietam National Battlefield
4.5/5(140 reviews)
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.
Swallow Falls State Park
5/5(29 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.
What to do in Western Maryland
City Cruises Baltimore: Signature Buffet Dinner Cruise with Live DJ & Bars
$137
per adult
84% of travellers recommend
City Cruises Baltimore: Signature Lunch Cruise
$69
per adult
Glow in the Dark Splatter Paint Experience
$40
per adult
78% of travellers recommend
Western Maryland Hotel Deals
Rocky Gap Casino & Resort
16701 Lakeview Road NE Cumberland MD
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $125 total per night from Dec 14 to Dec 15
$125 total
Dec 14 - Dec 15
Total with taxes and fees
8.8/10 Excellent! (1,386 reviews)
Beautiful lake and mountains. Relaxing stay
Reviewed on Nov 17, 2025
Hilton Garden Inn Frederick
7226 Corporate Ct Frederick MD
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $93 total per night from Nov 24 to Nov 25
$93 total
Nov 24 - Nov 25
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
Comfortable beds
Reviewed on Nov 13, 2025
Country Inn & Suites by Radisson, Frederick, MD
5579 Spectrum Dr Frederick MD
Fully refundable
$78 nightly
The price is $86 total per night from Dec 11 to Dec 12
$86 total
Dec 11 - Dec 12
Total with taxes and fees
8.2/10 Very Good! (1,183 reviews)
Front desk was efficient, room was nice and clean, stay was quiet and short.
Reviewed on Nov 13, 2025
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.
Find the Best Western Maryland Vacation Packages
Western Maryland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Washington Dulles Intl. Airport (IAD) |
More vacations you might like
Explore a world of travel with Expedia
- All-inclusive Resorts in Mid-Atlantic
- Oceanfront Hotels in Mid-Atlantic
- Beach Hotels in Mid-Atlantic
- Hotels with a Lazy River in Mid-Atlantic
- Resorts & Hotels with Spas in Mid-Atlantic
- Adults Only Resorts & in Mid-Atlantic
- Hotels & Resorts for Couples in Mid-Atlantic
- Ski Hotels in Mid-Atlantic
- Romantic Hotels in Mid-Atlantic
- Hotels with an Indoor Pool in Mid-Atlantic
- Great Wolf Lodge Hotels in Mid-Atlantic
- Luxury Hotels in Mid-Atlantic
- Golf Hotels in Mid-Atlantic
- Family Hotels in Mid-Atlantic
- Marriott Hotels & Resorts in Mid-Atlantic
- Hotels with an Outdoor Pool in Mid-Atlantic
- Pet-friendly Hotels in Mid-Atlantic
- Honeymoon Resorts & in Mid-Atlantic
- Hotels with Waterslides in Mid-Atlantic
- Casino Hotels in Mid-Atlantic
- B&B in Mid-Atlantic
- Historic Hotels in Mid-Atlantic
- Fishing Resorts & in Mid-Atlantic
- Gay friendly Hotels in Mid-Atlantic
- Mid-Atlantic Hotels
- Hotels on the Lake in Mid-Atlantic
- Winery Hotels in Mid-Atlantic
- Hyatt Hotels in Mid-Atlantic
- 5 Star Hotels in Mid-Atlantic
- Hotels with Fireplaces in Mid-Atlantic
- Hotels with a View in Mid-Atlantic
- Boutique Hotels in Mid-Atlantic
- Quiet Resorts & in Mid-Atlantic
- Resorts in Mid-Atlantic
- Cottages in Mid-Atlantic
- Hotels with Connecting Rooms in Mid-Atlantic
- Relais & Chateaux Hotels in Mid-Atlantic
- Hotels with a Pool in Mid-Atlantic
- Houseboats in Mid-Atlantic
- Hotel Wedding Venues Hotels in Mid-Atlantic
- Motels in Mid-Atlantic
- Hotels with Balconies in Mid-Atlantic
- Cheap Hotels in Mid-Atlantic
- Waterpark Hotels in Mid-Atlantic
- RV Parks in Mid-Atlantic
- Condo Rentals in Mid-Atlantic
- Hotels with Hot Tubs in Mid-Atlantic
- Cabin Rentals in Mid-Atlantic
- Hostels in Mid-Atlantic
- Hilton Hotels in Mid-Atlantic
- MGM Hotels in Mid-Atlantic
- Kimpton Hotels in Mid-Atlantic
- Diamond Resorts in Mid-Atlantic
- Hotels with Early Check-in in Mid-Atlantic
- Guest Houses in Mid-Atlantic
- Benchmark Hotels in Mid-Atlantic
- Starwood Capital Hotels in Mid-Atlantic
- Hotels with a Swim-up Bar in Mid-Atlantic
- Apartments in Mid-Atlantic
- Castles in Mid-Atlantic
- Condo Resorts in Mid-Atlantic
- Car rentals near Mid-Atlantic
- Hertz Rental Cars in Mid-Atlantic
- Nextcar Rental Cars in Mid-Atlantic
- Greenmotion Rental Cars in Mid-Atlantic
- Drive-A-Matic Rental Cars in Mid-Atlantic
- Localiza Uruguay Rental Cars in Mid-Atlantic
- Easirent.com Rental Cars in Mid-Atlantic
- Midsize Car Rentals in Mid-Atlantic
- Economy Rent a Car Rental Cars in Mid-Atlantic
- Europcar Rental Cars in Mid-Atlantic
- Car rentals near Anacostia River
- Right Cars Rental Cars in Mid-Atlantic
- Alamo Rent A Car Rental Cars in Mid-Atlantic
- Turisprime Rental Cars in Mid-Atlantic
- Owners Rental Cars in Mid-Atlantic
- WIber Rental Cars in Mid-Atlantic
- Buchbinder Rental Cars in Mid-Atlantic
- Dirent Rental Cars in Mid-Atlantic
- Guerin Rental Cars in Mid-Atlantic
- Rent A Wreck Rental Cars in Mid-Atlantic
- Pickup Car Rentals in Mid-Atlantic
- Rhodium Rental Cars in Mid-Atlantic
- Luxury Car Rentals in Mid-Atlantic
- Goldcar Key’n Go Rental Cars in Mid-Atlantic
- Avis Canaries Rental Cars in Mid-Atlantic
- Thrifty Car Rental Rental Cars in Mid-Atlantic
- Rentscape Rental Cars in Mid-Atlantic
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
