Oldtown Vacations from $156
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The Latest Oldtown vacation packages
Price found within the past 48 hours. Click for updated prices.
Wayside Inn
$156
per person
Dec 4 - Dec 7
found 5 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Martinsburg (MRB)
9.2/10 Wonderful! (449 reviews)
This is an old inn built in the late 1700’s which is lovingly maintained. We were unable to be there when Clems kitchen is open but have heard it is very good.
Reviewed on Oct 20, 2026
Stay near popular Oldtown attractions
Paw Paw Tunnel
10.0/10 (1 review)
Find out about the history of Oldtown with a stop at Paw Paw Tunnel. Amble around this romantic area's forest, or seek out the hiking trails.
Oldtown Hotel Deals
Rocky Gap Casino & Resort
16701 Lakeview Road NE Cumberland MD
$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
6.8/10 (1,005 reviews)
"The problem was no live help available! Just people on screens...almost like robots! And no help when you needed it, answering questions, etc. Tried to evict us after 2 days! Made us change rooms with 2 children."
Reviewed on Oct 20, 2026
Dreamtime - Modern A-frame Cabin w/ Hot tub
Berkeley Springs WV
$338 nightly
$376 total
Nov 5 - Nov 6
Total with taxes and fees
9.8/10 Exceptional! (76 reviews)
"This cabin is a perfect getaway surrounded by the forest. We loved the hot tub and wood-burning stove. We didn't have any issues and all communication with the host was smooth!"
Reviewed on Oct 5, 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 Oldtown Vacation Packages
Oldtown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 85 |
Top Sights | Rocky Gap State Park, Chesapeake and Ohio Canal National Historical Park and Tri-State Zoological Park |
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Frequently asked questions
How much does an Oldtown vacation package cost?
Offering excellent value package deals from $156 on Expedia, you'll be thrilled with how little a vacation to Oldtown costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Oldtown?
November, December and January are great times to look for cheap Oldtown vacation packages. Choosing to travel in less busy periods means you'll typically find lower prices on hotels and flights.
How many days is enough for Oldtown?
With a well-organized schedule, you can easily hit the top Oldtown attractions in a handful of days. But if you want to discover hidden gems or take day trips, consider booking your Oldtown vacation for longer.
How to find the best Oldtown package deals?
Use Expedia's handy filters to find some great Oldtown package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Oldtown package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book an Oldtown vacation as a package?
You can enjoy significant savings on your Oldtown break by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to view some great hotel prices and airfares. Bundle everything into a great-value 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 Oldtown?
If you're considering a spontaneous Oldtown getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Oldtown vacation packages?
Your Oldtown break should be an escape from your busy life, not a source of money-related stress. So to give you a little more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
