Oldtown Vacations from $486

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The Latest Oldtown vacation packages

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

Wayside Inn

3.5 out of 5
Price was $536, price is now $486 per person
$486
per person
Jan 11 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Martinsburg (MRB)
9.2/10 Wonderful! (407 reviews)
Friendly staff, historic atmosphere, terrific restaurant. Entire hotel was furnished with antiques, including the guest rooms

Reviewed on Oct 28, 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 relaxing area's forest, or seek out the hiking trails.

Paw Paw Tunnel

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.

Chesapeake and Ohio Canal National Historical Park

Oldtown Hotel Deals

Rocky Gap Casino & Resort

Rocky Gap Casino & Resort

3 out of 5
16701 Lakeview Road NE, Cumberland, MD
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $125 total per night from Dec 7 to Dec 8
$125 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (1,361 reviews)
The resort is beautiful, is in a gorgeous setting and was clean and comfortable. The casino was small, but just the right size, the main restaurant downstairs was delicious! The price of rooms for the weekend we stayed was super reasonable. Will be coming back in the summer months to enjoy the beach ...

Reviewed on Nov 3, 2025

Rocky Gap Casino & Resort
Ramada by Wyndham Cumberland Downtown

Ramada by Wyndham Cumberland Downtown

3 out of 5
100 South George Street, Cumberland, MD
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $90 total per night from Nov 23 to Nov 24
$90 total
Nov 23 - Nov 24
Total with taxes and fees
6.8/10 (1,005 reviews)
The property is in need of a refresh

Reviewed on Nov 6, 2025

Ramada by Wyndham Cumberland Downtown
Dreamtime - Modern A-frame Cabin w/ Hot tub

Dreamtime - Modern A-frame Cabin w/ Hot tub

Berkeley Springs
$342 nightly
The price is $380 total per night from Dec 3 to Dec 4
$380 total
Dec 3 - Dec 4
Total with taxes and fees
9.8/10 Exceptional! (48 reviews)
Hot tub was very clean, in fact chemical service came on second day of stay. House is tastefully decorated, with large tub downstairs that my wife loved and a great Marshall Bluetooth speaker. Walkable distance to hiking trail. Peace and quiet in the woods, in fact only saw one other resident while ...

Reviewed on Oct 14, 2025

Dreamtime - Modern A-frame Cabin w/ Hot tub
See all 578 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.

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 $486 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.