Woodland Vacations from $413
Book a Hotel + Flight or Car together to unlock savings
Your Woodland Vacation
The fascinating city of Woodland is calling your name. Delve into everything from its highlights to its hidden gems with a Woodland vacation package that's custom made for you. If sightseeing is on the agenda during your trip to Woodland, swing by well-known attractions like Frostburg State University, Noahs Ark and Palace Theater. Expedia is here to help you escape your routine. Tailor your vacation to Woodland to suit your style of travel, whatever that may be!
The Latest Woodland vacation packages
Price found within the past 48 hours. Click for updated prices.
Sleep Inn & Suites Cumberland - LaVale
$413
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Kansas City (MCI) to Hagerstown (HGR)
9.2/10 Wonderful! (1,000 reviews)
Room was clean n large. Staff friendly n helpful. Breakfast was real good. Coffee was the best I have had in an Hotel ever..Will be back soon.
Reviewed on Oct 21, 2026
Woodland Hotel Deals
Rocky Gap Casino & Resort
16701 Lakeview Road NE Cumberland MD
Fully refundableReserve now, pay when you stay
$114 nightly
$130 total
Nov 16 - Nov 17
Total with taxes and fees
Ramada by Wyndham Cumberland Downtown
100 South George Street Cumberland MD
Fully refundableReserve now, pay when you stay
$72 nightly
$82 total
Nov 1 - Nov 2
Total with taxes and fees
Sleep Inn & Suites Cumberland - LaVale
13320 Ali Ghan Road NE Cumberland MD
Fully refundable
$80 nightly
$91 total
Nov 15 - Nov 16
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
"Room was clean n large. Staff friendly n helpful. Breakfast was real good. Coffee was the best I have had in an Hotel ever..Will be back soon."
Reviewed on Oct 21, 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.
Find the Best Woodland Vacation Packages
Woodland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Palace Theater, Thrasher Carriage Museum and Frostburg State University |
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Frequently asked questions
How much does a Woodland vacation package cost?
You'll find cheap prices from $413 on Expedia for your Woodland break. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Woodland costs.
What are the cheapest months to go to Woodland?
If you're hoping to book a cheap Woodland vacation package, consider visiting in December, January and February. You'll typically find better rates on hotels and airfares during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Woodland?
With a well-organized schedule, you can easily tick off the top Woodland sights in a handful of days. But if you'd like to discover hidden spots or go on day tours, consider booking your Woodland vacation for longer.
How to find the best Woodland package deals?
Finding a cheap Woodland package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply some filters and browse what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most wallet-friendly Woodland package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Woodland vacation as a package?
You can enjoy significant savings on your next Woodland break by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Woodland?
If you've got your Woodland vacation dates finalized, book early to snap up some awesome deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for impromptu escapes.
Does Expedia offer Book Now, Pay Later Woodland vacation packages?
If you're anything like us, you love exploring new places but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Woodland break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.