Oldtown Holidays

Photo by Kayla Berry

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Top hotels in Oldtown

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! (1,225 reviews)
"Great place to stay! Hotel, Casino, and restaurants are very clean and the outside area is beautiful!"

Reviewed on 9 Jul, 2025

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Rocky Gap Casino & Resort
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
The price is S$122 per night from 21 Jul to 22 Jul
S$122
21 Jul - 22 Jul
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"Nice place hidden in the middle of town out of view"

Reviewed on 9 Jul, 2025

Best Western Braddock Inn
The Country Inn of Berkeley Springs
The Country Inn of Berkeley Springs
3.5 out of 5
110 S Washington St, Berkeley Springs, WV
Fully refundableReserve now, pay when you stay
The price is S$188 per night from 16 Jul to 17 Jul
S$188
16 Jul - 17 Jul
includes taxes & fees
8.8/10 Excellent! (814 reviews)
"My wife has some pretty severe food allergies, I emailed ahead and spoke to their executive chef 2 weeks before our trip, he called me back went over specifics Of the allergens, and he was happy to accommodate ensuring no cross contamination and “safe” ingredients. He purchased specific ingredients ..."

Reviewed on 8 Jul, 2025

The Country Inn of Berkeley Springs
See all 549 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 holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday 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 holiday packages. Bear in mind that school holiday 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-organised 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 holiday 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 holiday package as early as possible.
Is it cheaper to book an Oldtown holiday as a package?
You can enjoy significant savings on your Oldtown break by booking a tailored holiday 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 holiday 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 favourite 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 holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.