Oldtown Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 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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    Plan, book, and manage your trip all in one place

Top Oldtown Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Wayside Inn

Wayside Inn

3.5 out of 5
per person
Sep 10 - Sep 17
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Martinsburg (MRB)
9.2/10 Wonderful! (396 reviews)
We stayed last year on July 4th. ...really liked it...decided to make it an annual event. I like the small town atmosphere.

Reviewed on Jul. 7, 2025

Ready to book your vacation to Oldtown?

 

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Oldtown Hotel Deals

Oldtown Guesthouse
Oldtown Guesthouse
Oldtown
The price is CA $144 per night from Jul 30 to Jul 31
CA $144
CA $254 total
Jul 30 - Jul 31
includes taxes & fees
10/10 Exceptional! (22 reviews)
Wonderful
"Sweet home, well decorated, clean and full of everything one needs for a short stay. Also delicious home baked goodies provided on arrival! Yum!"

Reviewed on Jun. 28, 2025

Oldtown Guesthouse
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
The price is CA $171 per night from Jul 27 to Jul 28
CA $171
CA $246 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (1,219 reviews)
"Our stay was great! All staff were very pleasant and accommodating. Signatures restaurant was very good!"

Reviewed on Jul. 7, 2025

Rocky Gap Casino & Resort
Dreamtime - Modern A-frame Cabin w/ Hot tub
Dreamtime - Modern A-frame Cabin w/ Hot tub
Berkeley Springs
10/10 Exceptional! (41 reviews)
Lovely Forest Retreat with All the Creature Comforts
"My husband and I visited for our anniversary. The cabin is lovely - beautifully renovated, thoughtfully outfitted, and situated in a lovely forested setting. The king-sized bed was the most comfortable bed that I have slept on away from home. The hot tub uses a saltwater system which is so much more ..."

Reviewed on May 24, 2025

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Dreamtime - Modern A-frame Cabin w/ Hot tub
See all 546 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

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Frequently asked questions

How much does an Oldtown vacation package cost?
You'll find cheap prices from CA $922 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.

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