Oldtown Vacation Packages

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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Oldtown Hotel Deals

Rocky Gap Casino & Resort

Rocky Gap Casino & Resort

4 out of 5
16701 Lakeview Road NE Cumberland MD
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Aug 2 to Aug 3
CA $139
CA $208 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (1,639 reviews)
"The room was clean and the amenities were good."

Reviewed on Jul 12, 2026

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 CA $119 per night from Aug 9 to Aug 10
CA $119
CA $136 total
Aug 9 - Aug 10
includes taxes & fees
7/10 Good! (1,008 reviews)
"………………………..pppp.gggggggggsssssssssss"

Reviewed on Jul 12, 2026

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 CA $113 per night from Jul 16 to Jul 17
CA $113
CA $129 total
Jul 16 - Jul 17
includes taxes & fees
8/10 Very good! (1,020 reviews)
"Old everything. Smelled of cigarettes and mold. One outlet in bathroom and on opposite wall from vanity. Shower curtain torn and falling off. This should not be listed as a Best Western as it meets no Best Western standards. Would definitely have checked out and gone elsewhere but no other hotels ..."

Reviewed on Jul 13, 2026

Best Western Braddock Inn
See all 601 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.
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Stay near popular Oldtown attractions

Paw Paw Tunnel

10.0/10 (1 review)
Find out about the history of Oldtown with a stop at Paw Paw Tunnel. Amble around this family-friendly area's forest, or seek out the hiking trails.
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Frequently asked questions

How much does an Oldtown vacation package cost?
You'll find cheap prices on Expedia for your Oldtown escape. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Oldtown costs.
What are the cheapest months to go to Oldtown?
The off-season is the best time to visit Oldtown if you're on a budget. Another tip for scoring cheap Oldtown vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Oldtown?
The ideal duration of your Oldtown vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you time to check out all the leading sights and explore some hidden gems along the way.
How to find the best Oldtown package deals?
Begin your search for an Oldtown package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Oldtown package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Oldtown adventure off to a flying start.
Is it cheaper to book an Oldtown vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and stays individually. Better still, you can customize your Oldtown getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Oldtown?
If you have your Oldtown vacation dates finalized, book as soon as you can to score some awesome deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Oldtown?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Oldtown.
  2. Set a budget: Consider costs like food, flights and transportation when calculating how much to set aside for your trip to Oldtown. Then, choose a property that fits your budget, whether that's an affordable stay or a swankier getaway.
  3. Decide how many days away: Start by listing all the sights and activities 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 hotels, flights, car rental and more into a personalized Oldtown vacation package.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.