Oldtown Vacations from $439

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The Latest Oldtown vacation packages

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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
$110 nightly
The price is $125 total per night from Jan 26 to Jan 27
$125 total
Jan 26 - Jan 27
Total with taxes and fees
8.8/10 Excellent! (1,463 reviews)
Rooms were very nice. Clean and confortable. The staff is helpful and very nice.

Reviewed on Jan 23, 2026

Rocky Gap Casino & Resort
Dreamtime - Modern A-frame Cabin w/ Hot tub

Dreamtime - Modern A-frame Cabin w/ Hot tub

Berkeley Springs WV
9.8/10 Exceptional! (53 reviews)
We absolutely loved the Dreamtime A-frame cabin. The house is simply perfect with a well appointed kitchen, great fireplace, hot tub, and comfortable beds. I could not have asked for more.

Reviewed on Jan 8, 2026

Dreamtime - Modern A-frame Cabin w/ Hot tub
Sleep Inn & Suites Cumberland - LaVale

Sleep Inn & Suites Cumberland - LaVale

2.5 out of 5
13320 Ali Ghan Road NE Cumberland MD
Fully refundable
$93 nightly
The price is $106 total per night from Feb 15 to Feb 16
$106 total
Feb 15 - Feb 16
Total with taxes and fees
9.2/10 Wonderful! (1,004 reviews)
The room was clean and the hallways smelled wonderful. The heater was off so it was freezing in the room for the first hour. The breakfast was okay mostly prepackaged stuff and not fresh coffee It was from a machine staff was wonderful though

Reviewed on Jan 23, 2026

Sleep Inn & Suites Cumberland - LaVale
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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Frequently asked questions

How much does an Oldtown vacation package cost?
Offering excellent value package deals from $439 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?
November, December and January are great times to look for cheap Oldtown vacation packages. Choosing to travel in less busy periods means you'll typically find lower prices on hotels and flights.
How many days is enough for Oldtown?
With a well-organized schedule, you can easily hit the top Oldtown attractions in a handful of days. But if you want to discover hidden gems or take day trips, consider 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.
Does Expedia offer Book Now, Pay Later Oldtown vacation packages?
Your Oldtown break should be an escape from your busy life, not a source of money-related stress. So to give you a little more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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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.