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Oakland holiday lettings

We found 1,508 holiday rentals — enter your dates for availability

Select from 556 houses, 57 flats and other holiday rentals to find the perfect place for your stay in Oakland. Whether you're going on holiday with family or friends, holiday homes have the amenities that you expect for your stay, which might include a garden and hot tub. No matter what you're looking for, you'll find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Oakland

Showing deals for:28 Nov - 5 Dec

Image gallery for Sunset View: Lakefront Pet-Friendly + Hot Tub + Dock

Marina
10 out of 10 rating
Exceptional
(11 reviews)

Sunset View: Lakefront Pet-Friendly + Hot Tub + Dock

Swanton, MD

7% off
Price is £2,440
£349 nightly
Includes taxes & fees
Sunset View: Lakefront Pet-Friendly + Hot Tub + Dock

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Find out more about Oakland

Find out more about Oakland

Explore the lakeside setting in Oakland

The lake and riverfront provide a pleasant backdrop to your holiday home in Oakland. Renowned for its rafting, skiing and ecotours, this city welcomes all visitors. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Oakland

Are you hoping to discover things to do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Oakland a fun place to get away to. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Lodestone Golf Club (8.7 mi / 13.9 km)
  • Thousand Acres Lakeside Golf Course (9.1 mi / 14.6 km)
  • Wisp Resort (10.5 mi / 17 km)
  • Funland (11 mi / 17.6 km)
  • Hovatter's Wildlife Zoo (19.1 mi / 30.7 km)
  • Timberline Four Season Resort (25.7 mi / 41.4 km)

Exploring the natural features in Oakland

Travellers enjoy Oakland for its lakeside setting and riverfront. Whether you're an adventurous traveller or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Oakland. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Deep Creek Lake (8.7 mi / 13.9 km)
  • Cathedral State Park (8.8 mi / 14.2 km)
  • Deep Creek Lake State Park (9.7 mi / 15.6 km)
  • Cheat River (13.9 mi / 22.4 km)
  • Cannon Hill (14.5 mi / 23.3 km)
  • Blackwater Falls (20.7 mi / 33.4 km)

Transport to and around Oakland

The nearest airport is in Morgantown, WV (MGW-Morgantown Municipal), located 31.8 mi (51.2 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Elkins, WV (EKN-Randolph County), which is 43.3 mi (69.7 km) away.

Frequently asked questions

What is the best area to stay in Oakland when booking a holiday rental?
When considering a holiday rental in Oakland, Maryland, the best area to stay is near the picturesque Deep Creek Lake. This scenic locale is great for those looking to enjoy both relaxation and adventure. The region boasts a variety of charming properties, with numerous rentals available, ensuring you can find something that fits your needs, whether it's a cosy cabin or a larger family home.

Staying close to Deep Creek Lake provides easy access to a wealth of outdoor activities. The lake itself is a major attraction, ideal for boating, fishing, and swimming during the warmer months, while in winter, visitors can enjoy nearby ski resorts such as Wisp Resort. Furthermore, the area is surrounded by stunning natural beauty, making it great for hiking and exploring nature trails.

Another appealing neighbourhood is the historic downtown Oakland area, which offers a blend of quaint shops, local eateries, and cultural sites. Here, you can explore the fascinating Oakland B&O Railroad Museum or take a leisurely stroll through the charming streets lined with Victorian architecture.
How much does it cost to rent a holiday home in Oakland?
Prices for holiday rentals in Oakland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Oakland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Oakland holiday house rentals?
You can find great discounts on house rentals in Oakland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Oakland?
For renting a beach house in Oakland, Maryland, the area surrounding Deep Creek Lake is the prime location to consider. This picturesque lake offers a variety of holiday rentals that cater to different group sizes, from cosy cabins to expansive lakefront homes. Many properties in this area come equipped with amenities such as private docks, fire pits, and outdoor decks, great for enjoying the stunning views and the serene atmosphere of the lake.

In addition to the lake itself, the nearby state parks, such as Swallow Falls State Park, provide opportunities for outdoor activities like hiking and picnicking, with some rentals offering easy access to these natural attractions. You can expect many accommodations to have features like fully equipped kitchens, hot tubs, and game rooms, making them ideal for families or friends looking to relax after a day of exploration.
Where are the best Oakland ski resort rentals?
For skiing near Oakland, Maryland, the closest resort is Wisp Resort, located just a short drive away. In the Oakland area, travellers will find a variety of rental options that provide convenient access to the slopes. Many properties in the vicinity feature comfortable amenities such as fully equipped kitchens, spacious living areas, and outdoor decks, superb for relaxing after a day of skiing.

Accommodations in the Deep Creek Lake area, which encompasses Oakland, range from charming lakeside cabins to modern townhouses. These rentals often include essentials like Wi-Fi, heating for those colder months, and in some cases, hot tubs or game rooms for added entertainment. The neighbourhood also offers proximity to local shops and restaurants, enhancing the overall experience for visitors.
What is the most popular type of holiday rental accomodation in Oakland?
In Oakland, holiday houses are the most popular type of rental, with around 408 available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and inviting living areas, making them ideal for families or groups looking to enjoy the picturesque surroundings. Many houses also include outdoor spaces such as decks or patios, great for relaxing after a day spent exploring the beautiful lakes and mountains nearby.

Cottages are also a sought-after option, with about 95 scattered around Oakland. These charming accommodations often provide a quaint and cosy atmosphere, complete with kitchen facilities and comfortable seating areas. For those seeking a rustic experience, roughly 79 cabins are available, offering a more secluded feel with access to nature, plus amenities like fireplaces and porches for enjoying the serene environment.
Are there any family house rentals in Oakland?
In Oakland, Maryland, there are numerous family-friendly holiday rentals available, with around 437 options to choose from. This charming area is great for families looking to enjoy a lakeside retreat, with properties located near Deep Creek Lake, known for its recreational activities such as swimming, boating, and fishing.

Visitors can find spacious homes equipped with amenities such as full kitchens for preparing family meals, large living rooms for gatherings, and outdoor decks or patios that offer beautiful views of the surrounding nature. Many rentals also come with features like game rooms, private hot tubs, and even access to community amenities like pools and playgrounds, ensuring plenty of entertainment for younger guests.
Can I rent a holiday home with a pool or hot tub in Oakland?
In Oakland, Maryland, there are many holiday homes available for rent that feature pools and hot tubs, with around 181 options to choose from. This picturesque area, located in the mountains of western Maryland, offers a serene escape with its natural beauty and proximity to Deep Creek Lake. Here, travellers can find rentals in various neighbourhoods, including those close to the lake where properties often come with private pools, hot tubs, and spacious outdoor decks great for enjoying the scenic surroundings.
Can I find long-stay holiday rentals in Oakland?
A long-stay holiday rental in Oakland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Oakland?
In Oakland, Maryland, there are numerous pet-friendly house rentals available, offering a variety of options for travellers with pets. Many of these properties are situated near Deep Creek Lake, providing stunning lake views and easy access to water activities. Expect to find amenities such as spacious backyards, outdoor decks, and sometimes even private docks, making them ideal for families or groups looking to enjoy the outdoors with their furry companions.
Are there any remote work holiday rentals in Oakland?
In Oakland, Maryland, there are numerous remote work-friendly holiday rentals available—around 622 properties to choose from. This charming area is surrounded by the natural beauty of Deep Creek Lake and the Appalachian Mountains, making it a peaceful retreat for those looking to blend work and leisure. Many of these rentals come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated office spaces, ergonomic desks, and computer monitors. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Oakland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Oakland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Oakland?
In Oakland, Maryland, holiday rentals commonly feature a range of amenities that enhance the comfort and convenience of guests. Most properties include kitchens equipped with essential cookware, dishware, and utensils, allowing travellers to prepare their own meals. Additionally, guests can expect free Wi-Fi in their accommodations, making it easy to stay connected. Many rentals also offer a microwave for quick meal preparations and patios where visitors can relax outdoors and enjoy the natural surroundings.
When is the best time to visit Oakland for a holiday rental?
The best time to visit Oakland for a holiday rental is during the peak season from July to September. This period draws families and outdoor enthusiasts eager to take advantage of the warm weather and various recreational activities. With temperatures typically ranging from the mid-teens to low 20s Celsius, it's an ideal time for hiking, boating, and enjoying the stunning natural beauty of Deep Creek Lake and the surrounding areas.

July stands out as the busiest month, bustling with visitors who flock to Oakland for its vibrant summer events and outdoor adventures. This lively atmosphere enhances the charm of the town, making it a fantastic time for those seeking a community feel while indulging in activities like fishing, kayaking, or simply soaking up the sun at local parks.

For those looking for a more budget-friendly option, consider planning your visit in December. Although this is the low season, it offers a great experience with the picturesque winter landscapes superb for cozy getaways. The holiday decorations add a festive touch, making it an excellent time for quiet reflection and enjoying the local charm at a slower pace.
How early should I book a Oakland holiday rental?
Book your Oakland holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Oakland?
In Oakland, Maryland, visitors can explore a variety of attractions that showcase the area's natural beauty and recreational opportunities. Deep Creek Lake is a major highlight, offering activities such as boating, fishing, and swimming, with numerous waterfront holiday rentals available nearby. The surrounding state parks, including Swallow Falls State Park, are superb for hiking and feature breathtaking waterfalls and scenic trails.
Can I change or cancel my Oakland home rental booking on Vrbo?
To find Oakland holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Oakland holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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