Oakland Holidays

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Your Oakland Holiday

When a city break is calling, answer it with a holiday package to Oakland. The neighbourhood of Blakeslee, which is great for nature, watersports and views, makes a great base for your adventures. If taking in the sights is a must during your trip to Oakland, be sure to swing by big-name attractions like Swallow Falls State Park and Herrington Manor State Park. No matter your travel plans or budget, organising a tailored Oakland holiday is a cinch with Expedia.

Our guide on where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
A waterfall cascading over rocks into a clear pool.

Mountainside

Mountainside might not have many top sights, but Deep Creek Lake and Deep Creek Lake State Park are two attractions nearby that you can check out.

Find hotels in Mountainside

Oakland Holiday

Oakland Essential Information

Language
English
Currency
U.S dollars
Population
1,900
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Herrington Manor State Park, Wolf Den Run State Park and Swallow Falls State Park

Our pick of the best Oakland Hotel Deals

Baja Motel

Baja Motel

2 out of 5
1501 Maryland Hwy Oakland MD
Fully refundableReserve now, pay when you stay
The price is AU$163 per night from 31 Oct to 1 Nov
AU$163
31 Oct - 1 Nov
includes taxes & fees
9/10 Wonderful! (145 reviews)
"I was in town for a wedding. Motel was only 20 minutes away from site. The gentleman that checked me in and out was great! I think he also did double duty cleaning the rooms. I had a handicapped room, dealing with a broken hip and knee. Room was amazing! The restaurant next door was nice too!"

Reviewed on 29 Oct 2026

Baja Motel
The Garrett Inn

The Garrett Inn

2.5 out of 5
17848 Garrett Highway Oakland MD
Fully refundableReserve now, pay when you stay
The price is AU$225 per night from 10 Nov to 11 Nov
AU$225
10 Nov - 11 Nov
includes taxes & fees
9.6/10 Exceptional! (464 reviews)
"When we arrived to the Garrett Inn, we were able to check in, and were given a key to the room, and told where to park (each room's number was plainly painted on the space for each room, however, due to the configuration of the parking lot vs the way the room's were situated, the parking spaces were ..."

Reviewed on 19 Oct 2026

The Garrett Inn
Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Oakland MD
9.6/10 Exceptional! (24 reviews)
"The place was very beautiful and nice. We enjoyed our stay a lot! Thank you for all your help."

Reviewed on 28 Sept 2026

Get rates
Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp
See all 766 properties in Oakland
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 Oakland attractions

A waterfall cascading over a rocky cliff surrounded by lush greenery.

Swallow Falls State Park

9.8/10 (138 reviews)
Maryland's highest free-falling waterfall cascades 53 feet at Swallow Falls State Park. Wander through ancient hemlock forests and listen to the soothing rush of water along well-maintained trails.
See properties

Frequently asked questions

How much does an Oakland holiday package cost?
You'll find cheap prices on Expedia for your Oakland getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your holiday to Oakland costs.
What are the cheapest months to go to Oakland?
You're likely to find lower rates and greater availability in March, April and November. Take a look at our cheap Oakland holiday packages and you could score some great off-season deals.
How many days is enough for Oakland?
With a well-organised itinerary, you can easily hit the most popular Oakland sights in a few days. But if you prefer to venture off the beaten track or go on day tours, consider booking your Oakland holiday for longer.
How to find the best Oakland package deals?
Finding a cheap Oakland package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can customise your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical Oakland package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book an Oakland holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and hotels individually. Better still, you can tailor your Oakland escape to match your exact needs. 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 holiday package to Oakland?
If you've got your Oakland holiday dates locked in, book early to score some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Oakland?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Oakland.
  2. Plan your budget wisely: As well as the price of your stay, you should consider other expenses too. These include transportation, flights and food. Also, set aside a little extra for unexpected costs that could arise during your trip to Oakland.
  3. Set the duration of your trip: Start by making a list of all the attractions you'd like to get to in Oakland. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to choose an Oakland holiday package that brings all your bookings together.

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