Oldtown Vacations

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    Save up to ￥45,448 when you book a flight and hotel together*
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Find the Best Oldtown Vacation Packages

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
8.8/10 Excellent! (1,203 reviews)
"Excellent overall, albeit pricy"

Reviewed on Jun 22, 2025

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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
The price is ￥12,418 per night from Jul 1 to Jul 2
￥12,418
￥14,156 total
Jul 1 - Jul 2
includes taxes & fees
6.8/10 (1,005 reviews)
"Very clean every time I stay there"

Reviewed on Jun 15, 2025

Ramada by Wyndham Cumberland Downtown
Dreamtime - Modern A-frame Cabin w/ Hot tub
Dreamtime - Modern A-frame Cabin w/ Hot tub
Berkeley Springs
The price is ￥42,220 per night from Jul 24 to Jul 25
￥42,220
￥53,016 total
Jul 24 - Jul 25
includes taxes & fees
10/10 Exceptional! (41 reviews)
Lovely Forest Retreat with All the Creature Comforts
"My husband and I visited for our anniversary. The cabin is lovely - beautifully renovated, thoughtfully outfitted, and situated in a lovely forested setting. The king-sized bed was the most comfortable bed that I have slept on away from home. The hot tub uses a saltwater system which is so much more ..."

Reviewed on May 24, 2025

Dreamtime - Modern A-frame Cabin w/ Hot tub
See all 529 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.

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?
Plan your getaway for the low season and you're likely to score cheap Oldtown vacation packages. Bear in mind that school vacation periods and local events and festivals can have an impact on prices, so do your research before you go.
How many days is enough for Oldtown?
With a well-organized schedule, you can easily tick off the top Oldtown attractions in a few days. But if you want to discover lesser-known spots or go on day trips, think about 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.
How to plan a trip to Oldtown?

  1. Choose when to go: Check your calendar and get your bags packed. Your favorite time of year and the available activities will also help you decide when to visit Oldtown.
  2. Set a budget: Consider costs like food, flights and transportation when working out how much to save for your trip to Oldtown. Then, pick a property that works with your budget, whether that's an economical option or a lavish getaway.
  3. Determine how many days away: Start by making a list of all the attractions you'd like to experience in Oldtown. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a tailored Oldtown vacation package.

Discover the most popular places to visit in Oldtown

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 romantic area's forest, or seek out the hiking trails.

Chesapeake and Ohio Canal National Historical Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.