Oakland Holidays

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Your Oakland Holiday

When a fun 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 wonderful base for your adventures. If going to see the sights is a priority during your trip to Oakland, be sure to swing by popular attractions like Swallow Falls State Park and Herrington Manor State Park. No matter your travel plans or the size of your budget, putting together a tailored Oakland holiday is a cinch with Expedia.

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 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

Top hotels in Oakland

Baja Motel

Baja Motel

2 out of 5
1501 Maryland Hwy Oakland MD
Fully refundableReserve now, pay when you stay
The price is £94 per night from 24 Nov to 25 Nov
£94
24 Nov - 25 Nov
includes taxes & fees
Baja Motel
The Garrett Inn

The Garrett Inn

2.5 out of 5
17848 Garrett Highway Oakland MD
The price is £95 per night from 15 Nov to 16 Nov
£95
15 Nov - 16 Nov
includes taxes & fees
9.6/10 Exceptional! (467 reviews)
"We appreciated the “old school” motel experience. Our room was extremely clean and housekeeping was a bonus! We were thankful for a cost efficient option compared to other area options. The hosts communicated promptly."

Reviewed on 12 Nov 2026

The Garrett Inn
Cove Creek Lodge

Cove Creek Lodge

2 out of 5
19638 Garrett Hwy Oakland MD
The price is £151 per night from 24 Nov to 25 Nov
£151
24 Nov - 25 Nov
includes taxes & fees
Cove Creek Lodge
See all 763 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

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

Why should I book my Oakland holiday with Expedia?
Choose Expedia to organise your next big break simply and all in one place. Our top tip for getting an unbeatable deal on an Oakland retreat? Bundle your accommodation, flights and/or car hire into a package holiday. Then add a few exciting tours and activities. Most bookings also come with flexible cancellation policies, so there's no need to panic if you have to switch up your travel plans. Round-the-clock assistance with amending and cancelling your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Oakland?
Enjoy sightseeing but don't like queuing up for attractions? Plan your Oakland escape for July, August and December. Typically, it's a lot quieter than it is in January, April and May. To give you an idea of what type of weather you can experience, the average daytime temperature in January, the coolest month in Oakland, is -3ºC. The warmest month here is July, when temperatures reach around 20ºC.
What are the top hotels for my holiday in Oakland?
If you're planning to stay in the Blakeslee neighbourhood, Inn At Deep Creek and Linwood: Lake Access, Dogs Welcome, Dock Slip, Fire Pit! are great options. The View is another popular Oakland area. We recommend Serendipity or Serendipity if you choose this part of the city.
How do I get a cheap holiday to Oakland?
One of the simplest ways to save pounds (and time) is to combine your bookings with Expedia. Hotels, flights, activities and hire cars — we've got them all. Pick a combination that suits your style and watch your savings stack up. Of course, holidays are never a one-size-fits-all. That's why we offer over 400 partner airlines and 321,000 hotel options throughout the world, so you can customise your Oakland holiday your way. Learn more about how you can save money on your next holiday when you book a flight and hotel together with Expedia.
What should I do on my Oakland holiday?
Make sure your next holiday in Oakland is one to remember by taking in its major attractions. Swallow Falls State Park, Herrington Manor State Park, Garrett Regional Medical Centre and Wolf Den Run State Park are among the things you should see while you're in the area.
What is the best area to stay in when on holiday in Oakland?
There's plenty to do in Oakland, so spend your nights near its attractions and maximise your time sightseeing. Swallow Falls State Park is one place that should be on your itinerary.
Do I need a visa for my Oakland holiday?
Check the latest rules on official government websites. Your nationality and whether you're travelling for business, study or leisure will determine if you'll need a visa for Oakland. Find out about the application process, including the required documentation, fees and turnaround times. Finalise your application well in advance to allow enough time for processing. Some visas can take several weeks or even months to obtain, depending on the country and time of year.
What should I wear on my Oakland holiday?
Consider the type of activities planned during your holiday in Oakland and take versatile pieces that you can mix and match. For fashion inspiration or even information on dress codes, look up a few style blogs or relevant social media accounts. Be sure to check the weather forecast so you can pack your bags accordingly. The warmest time of year in Oakland is July, with average daily temperatures of 20ºC. If you're visiting in the coolest month of January, the mercury averages -3ºC during the day.
What does an Expedia Oakland holiday include?
Hotels, car hires and flights, or any combination of them — it's your pick! Whether you're exploring Oakland on a family road trip or adventuring with your friends, there's a package to match your budget and style. Once you've made your booking, why not add on a few tours and experiences? Expedia features all kinds of properties, with the most popular in Oakland being private holiday homes and cabins. With Expedia, you'll always enjoy the flexibility and freedom to design your dream escape your way.
Does Expedia offer Book Now, Pay Later Oakland holidays?
Your bank balance shouldn't prevent you from escaping on holiday, so Expedia has devised a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a terrific getaway without hurting your hip pocket. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your break. Consider one of these flexible payment options:

  • Pay monthly holidays: If paying across multiple transactions works for you, Klarna can help. Paying in multiple instalments will make your getaway dreams come true.
  • No-deposit holidays: If no upfront fee for your trip makes pressing that "book now" button easier, choose a no-deposit holiday plan from Klarna so you can Book Now, Pay Later!

Can I choose my airline with an Oakland Expedia holiday?
Definitely. Expedia has more than 400 airline partners to choose from across the world. With so much choice, finding the right carrier to bring you to Oakland shouldn't be hard.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.