Oldtown Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Kayla Berry

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! (1,257 reviews)
"Could use better pillows otherwise room was great. Would love to see a buffet but not necessary"

Reviewed on 15 Aug 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 2.121.464 ₫ per night from 20 Aug to 21 Aug
2.121.464 ₫
2.418.469 ₫ total
20 Aug - 21 Aug
includes taxes & fees
6.8/10 (1,002 reviews)
"Nice place for the price"

Reviewed on 14 Aug 2025

Ramada by Wyndham Cumberland Downtown
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 2.034.504 ₫ per night from 1 Sept to 2 Sept
2.034.504 ₫
2.319.292 ₫ total
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"While traveling it was a good place to sleep. Appeared clean and well lit."

Reviewed on 5 Aug 2025

Best Western Braddock Inn
See all 551 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.

Popular places to visit

Paw Paw Tunnel

Paw Paw Tunnel

Find out about the history of Oldtown when you spend time at Paw Paw Tunnel. Amble around this family-friendly area's forests 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 forests or seek out the hiking trails.

Chesapeake and Ohio Canal National Historical Park

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.