Oldtown Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Kayla Berry
    deals illustration
    Better together
    Save up to Rp173.195 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

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! (1,199 reviews)
"Beautiful views, nice casino, comfy beds. The lakeside grille had excellent food while signatures bar and grill left a lot to be desired when it came to the food. Overall great place and we had a great time!"

Reviewed on 18 Jun 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 Rp1.393.745 per night from 1 Jul to 2 Jul
Rp1.393.745
Rp1.588.870 total
1 Jul - 2 Jul
includes taxes & fees
6.8/10 (1,001 reviews)
"Convenience and great location for me. In the center of all I needed and wanted to do. Nice rates"

Reviewed on 20 Jun 2025

Ramada by Wyndham Cumberland Downtown
Keyser Inn
Keyser Inn
2.5 out of 5
51 Josie Drive, Keyser, WV
Fully refundableReserve now, pay when you stay
The price is Rp1.229.775 per night from 23 Jun to 24 Jun
Rp1.229.775
Rp1.377.348 total
23 Jun - 24 Jun
includes taxes & fees
8.8/10 Excellent! (841 reviews)
Clean and Comfortable
"No bells and whistles but if you need a place to crash, this will meet your needs. They do offer a complimentary breakfast but we didn’t partake. There are NO elevators so keep that in mind if you’re not able to handle stairs easily and you get roomed on the 2nd or 3rd floor."

Reviewed on 16 Jun 2025

Keyser Inn
See all 531 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.