Oldtown Vacations from $196

Book a Hotel + Flight or Car together to unlock savings

Photo by Kayla Berry

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Oldtown vacation packages

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

Econo Lodge Inn & Suites

2 out of 5
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Martinsburg (MRB)
5.6/10 (284 reviews)
Great place to sleep and its was very quiet.

Reviewed on Jun 24, 2025

Wayside Inn

Wayside Inn

3.5 out of 5
per person
Oct 16 - Oct 20
found 6 hours ago
Roundtrip flight included
Knoxville (TYS) to Martinsburg (MRB)
9.2/10 Wonderful! (402 reviews)
We stayed last year on July 4th. ...really liked it...decided to make it an annual event. I like the small town atmosphere.

Reviewed on Jul 7, 2025

Don't see what you're looking for?
See all available trips from Columbus to Oldtown
View all trips

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

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

Chesapeake and Ohio Canal National Historical Park

Explore the great outdoors at Chesapeake and Ohio Canal National Historical Park, a lovely green space in Oldtown. Amble around this romantic area's forest, or seek out the hiking trails.

Chesapeake and Ohio Canal National Historical Park

Oldtown Hotel Deals

Oldtown Guesthouse

Oldtown Guesthouse

Oldtown
$175 nightly
The price is $186 total per night from Aug 13 to Aug 14
$186 total
Aug 13 - Aug 14
Total includes taxes and fees
10/10 Exceptional! (23 reviews)
Wonderful
"Sweet home, well decorated, clean and full of everything one needs for a short stay. Also delicious home baked goodies provided on arrival! Yum!"

Reviewed on Jun 28, 2025

Oldtown Guesthouse
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
$152 nightly
The price is $173 total per night from Sep 1 to Sep 2
$173 total
Sep 1 - Sep 2
Total includes taxes and fees
8.8/10 Excellent! (1,257 reviews)
"We had a great stay. The resort is beautiful, but I wouldn't pay extra for a lakefront view or a separate sitting area. The extra space was just by the bed with a chair and ottoman."

Reviewed on Aug 3, 2025

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

Dreamtime - Modern A-frame Cabin w/ Hot tub

Berkeley Springs
$337 nightly
The price is $375 total per night from Aug 24 to Aug 25
$375 total
Aug 24 - Aug 25
Total includes taxes and fees
10/10 Exceptional! (44 reviews)
"Cutest little house in the woods. We enjoyed the hot tub under the stars, and the very comfortable bed. It was quiet and relaxing in this home, and it was so nice to have the essentials provided (like coffee, sugar, creamer, garbage bags, paper towels, detergent). Very close to the brewery, and to ..."

Reviewed on Jul 16, 2025

Dreamtime - Modern A-frame Cabin w/ Hot tub
See all 538 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an Oldtown vacation package cost?
Offering excellent value package deals from $196 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.