Oldtown Vacation Packages 2026 from $376

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The Latest Oldtown vacation packages

Price found within the past 48 hours. Click for updated prices.

Wayside Inn

$376

per person

Jan 22 - Jan 26

found 21 hours ago

Roundtrip non-stop flight included

Seattle (SEA) to Martinsburg (MRB)

9.2/10 Wonderful! (413 reviews)

Brittany and the rest of the staff at Wayside were wonderful. They made us feel welcome, talked to us about the history and quirks of the, and our room was very quaint. The Christmas decorations in the room were a nice touch.

Reviewed on Nov 23, 2025

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Discover the most popular places to visit in Oldtown

This is a 3,118 foot long canal tunnel that is eerily dark and silent when you’re alone with no flashlight.
#adventure

Paw Paw Tunnel

5/5(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.

Chesapeake and Ohio Canal National Historical Park

5/5(1 review)

Explore the great outdoors at Chesapeake and Ohio Canal National Historical Park, a lovely green space in Oldtown. Amble around this relaxing 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

$110 nightly

$125 total

Dec 21 - Dec 22

Total with taxes and fees

8.8/10 Excellent! (1,410 reviews)

The place is immaculate. The staff super friendly. The restaurant food was great. My wife and I had a wonderful time

Reviewed on Dec 12, 2025

Dreamtime - Modern A-frame Cabin w/ Hot tub

Berkeley Springs WV

9.8/10 Exceptional! (50 reviews)

I took my Mother here for her 80th Bday getaway. It was so quiet and peaceful and relaxing. We had everything we needed. I was so impressed by the cleanliness and quaint decor of this A-Frame. The beds were wonderfully comfortable. We sat at the table and made dinners, did puzzles and listened to ...

Reviewed on Dec 7, 2025

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Ramada by Wyndham Cumberland Downtown

100 South George Street Cumberland MD

Fully refundableReserve now, pay when you stay

$76 nightly

$86 total

Dec 22 - Dec 23

Total with taxes and fees

6.8/10 (1,000 reviews)

Decent

Reviewed on Nov 22, 2025

See all 568 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 from $376 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 from $376

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