Oldtown Vacation Packages 2026

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Discover the most popular places to visit in Oldtown

Paw Paw Tunnel

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

Fully refundableReserve now, pay when you stay

$130 nightly

$148 total

May 25 - May 26

Total with taxes and fees

9/10 Wonderful! (1,572 reviews)

"Not a great hotel - the room didn’t smell too great, the walls were really thin (and guests were pretty loud in the halls through 3 am as the came back from the casino), and the hotel apparently doesn’t clean rooms during your stay except by request (which would have been nice to know in advance). ..."

Reviewed on May 24, 2026

Dreamtime - Modern A-frame Cabin w/ Hot tub

Berkeley Springs WV

10/10 Exceptional! (62 reviews)

"Loved this cabin. Absolutely gorgeous area. Highly recommend."

Reviewed on Apr 13, 2026

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Ramada by Wyndham Cumberland Downtown

100 South George Street Cumberland MD

Fully refundableReserve now, pay when you stay

$84 nightly

$96 total

May 27 - May 28

Total with taxes and fees

7/10 Good! (1,002 reviews)

"The video concierge was unsettling and there were no signs to indicate what it was. Snacks were unpackaged randomly on a shelf and unlabled and unpriced. Vending machines were inoperable, the breakfast was a decent spread but the water jugs looked like they were manually refilled instead of clean ..."

Reviewed on May 23, 2026

See all 587 properties in Oldtown

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.

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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 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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Cumberland Vacation Rentals

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

Oldtown Vacations

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Find the right fit

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