A river flowing through a forest with a waterfall.
Photo by KM Moore
Open Photo by KM Moore

Oakland Holidays

Book a Hotel + Flight or Car together to unlock savings

Where to stay in Oakland

Find the best Oakland areas for the activities you enjoy most.

Mountainside

Escape to Mountainside, a tranquil retreat nestled among Thayerville's wooded peaks near Deep Creek Lake. This peaceful mountain community offers a natural haven for travellers seeking quiet solitude. The rustic cabins blend seamlessly with the forested landscape. Nature lovers will find adventure just minutes away at Deep Creek Lake State Park. Nearby attractions include the Lodestone Golf Club and Adventure Sports Centre International. Mountain air carries pine scents while private wooded lots provide natural privacy between holiday homes.

Paradise Point

Paradise Point delivers the quintessential lake holiday experience on the shores of Deep Creek Lake. This waterfront area features private cabins and holiday homes tucked among towering trees. You'll have direct access to crystal-clear waters for swimming, fishing, and boating. The peaceful setting creates a perfect escape from everyday life. Enjoy morning mist rising off the water and evenings around a crackling campfire. While there are no shops or restaurants within Paradise Point itself, nearby Thayerville offers dining options and supplies for your lakeside retreat.

The View

The View in Thayerville offers the perfect lakeside retreat with direct access to Deep Creek Lake's crystal-clear waters. Private docks and waterfront homes create a peaceful escape for outdoor enthusiasts. Enjoy swimming, fishing, or kayaking right from your holiday rental's backyard. The surrounding Western Maryland landscape provides stunning natural beauty in every season. Nearby Deep Creek Lake State Park offers hiking trails and scenic mountain vistas. Most homes feature expansive windows that frame magnificent lake views and full kitchens for cosy meals after a day on the water.

Blakeslee

This quiet area in western Maryland offers a peaceful retreat near Deep Creek Lake's natural beauty. Blakeslee welcomes travellers seeking an authentic small-town American experience away from tourist crowds. The residential community provides a perfect base for outdoor adventures in the surrounding Appalachian forests. Holiday rentals and cabins dot this budget-friendly area where travellers can enjoy mountain views and fresh air. Nearby Deep Creek Lake offers boating, swimming and fishing just a short drive away. Golf enthusiasts will appreciate easy access to Thousand Acres Lakeside Golf Course during their stay.

Silver Ridge

Silver Ridge offers a peaceful lakeside retreat in the Deep Creek Lake area. This residential community features contemporary and traditional holiday homes nestled among mature trees. You'll appreciate the natural setting with forest surroundings and wildlife viewing opportunities. Many properties provide private docks or lake access. The area serves as an ideal base for outdoor activities. Deep Creek Lake State Park and nearby golf courses are just a short drive away. Crystal-clear mountain lake waters invite swimming, boating, and fishing throughout the seasons. Enjoy stargazing and quiet evenings after days filled with outdoor adventure.

Discover the most popular places to visit in Oakland

Oakland Hotel Deals

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.

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.