Oldtown Vacations from $621

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The Latest Oldtown vacation packages

Price found within the past 48 hours. Click for updated prices.
Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South

2 out of 5
Price was $670, price is now $621 per person
$621
per person
Jul 6 - Jul 11
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Martinsburg (MRB)
5.8/10 (308 reviews)
A bit pricey for the quality

Reviewed on Mar 24, 2026

Wayside Inn

Wayside Inn

3.5 out of 5
Price was $864, price is now $788 per person
$788
per person
Jul 6 - Jul 11
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Martinsburg (MRB)
9.2/10 Wonderful! (433 reviews)
Everything and everyone were great. The extra roll out bed was not.

Reviewed on May 28, 2026

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Discover the most popular places to visit in Oldtown

Paw Paw Tunnel

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.

Paw Paw Tunnel

Oldtown Hotel Deals

Rocky Gap Casino & Resort

Rocky Gap Casino & Resort

4 out of 5
16701 Lakeview Road NE Cumberland MD
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $148 total per night from Jun 14 to Jun 15
$148 total
Jun 14 - Jun 15
Total with taxes and fees
9/10 Wonderful! (1,576 reviews)
"Bed was comfortable. Parking definitely was the main issue. Spots should be allocated for guests who are staying in the resort and separate from those who just patronize the casino and grounds. Not offering at least coffee in the lobby free for resort guests was unfavorable as well."

Reviewed on May 30, 2026

Rocky Gap Casino & Resort
Dreamtime - Modern A-frame Cabin w/ Hot tub

Dreamtime - Modern A-frame Cabin w/ Hot tub

Berkeley Springs WV
$252 nightly
The price is $281 total per night from Jun 28 to Jun 29
$281 total
Jun 28 - Jun 29
Total with taxes and fees
10/10 Exceptional! (63 reviews)
"Great cabin! Hot tub was nice, house was very clean"

Reviewed on May 14, 2026

Dreamtime - Modern A-frame Cabin w/ Hot tub
Best Western Braddock Inn

Best Western Braddock Inn

2.5 out of 5
1268 National Hwy Cumberland MD
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $85 total per night from Jun 22 to Jun 23
$85 total
Jun 22 - Jun 23
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"Room was clean. Staff was helpful and friendly. The breakfast was horrible. Poor quality and variety of food."

Reviewed on May 27, 2026

Best Western Braddock Inn
See all 591 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 $621 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.