Photo by Jenn Charbonneau

Oakland holiday lettings

We found 1,536 holiday rentals — enter your dates for availability

Select from 472 houses, 53 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:22 May - 29 May

Image gallery for Creekside Log Cabin w/firepit, near quaint towns Thomas/Davis & many state parks

Authentic log cabin by the creek with hammock for total relaxation
10 out of 10, Exceptional, (40 reviews)
Exceptional
(40 reviews)

Creekside Log Cabin w/firepit, near quaint towns Thomas/Davis & many state parks

Aurora

8% off
Price is £1,060
for 7 nights, 1 cabin
£151 per night
includes taxes & fees
Creekside Log Cabin w/firepit, near quaint towns Thomas/Davis & many state parks

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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:

  • Wisp Resort (10.5 mi / 17 km)
  • Funland (11 mi / 17.6 km)
  • West Virginia Zoo (19.1 mi / 30.7 km)
  • Timberline Four Season Resort (25.7 mi / 41.4 km)
  • Canaan Valley Ski Resort (27.8 mi / 44.8 km)
  • Oakland Golf Course (1.1 mi / 1.8 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)
  • Cranesville Swamp Natural Area (9.6 mi / 15.4 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 area around Deep Creek Lake is one of the best choices. This picturesque neighbourhood offers a stunning natural setting, superb for those looking to enjoy outdoor activities such as boating, fishing, and hiking. Deep Creek Lake State Park is a highlight, featuring beautiful trails and scenic views that attract nature lovers year-round.

Another appealing area is the quaint town centre of Oakland itself. Here, visitors can engage in local culture and history, with attractions like the historic Oakland B&O Railroad Station and the splendid architecture found throughout the town. The availability of properties in both these areas is quite good, providing a range of options from cosy cabins to more spacious homes, making it easy to find the superb fit for your holiday needs.
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 around Deep Creek Lake is a prime choice. This picturesque lake offers a range of holiday rentals that cater to various tastes, from charming cabins to spacious lakefront homes. Many properties in this region come with desirable amenities such as private docks, outdoor fire pits, and expansive decks that provide stunning views of the lake, making them superb for gathering with family or friends.

The surrounding Oakland neighbourhood is known for its outdoor recreational opportunities, including boating, fishing, and hiking. Rentals often include access to kayaks or paddleboards, enhancing the lake experience. Additionally, properties may feature modern kitchens, hot tubs, and game rooms, ensuring a comfortable stay for all guests.

Nearby, the Wisp Resort offers year-round activities, including skiing in the winter and mountain biking during the summer, making this location ideal for those who enjoy both beach and adventure.
Where are the best Oakland ski resort rentals?
For ski resort rentals near Oakland, Maryland, the most prominent destination is the Wisp Resort, located just a short drive away in McHenry. Visitors looking for convenient accommodations will find a variety of options in and around McHenry, encompassing everything from cozy cabins to more spacious lodges suitable for families and groups. Many of these properties come equipped with amenities such as fireplaces, full kitchens, and outdoor decks, superb for enjoying the mountain views after a day of skiing.

In addition to Wisp Resort, the surrounding area offers charming properties in Oakland itself, where you can find lakeside cabins and rustic lodges that typically feature modern conveniences like hot tubs, Wi-Fi, and laundry facilities. These rentals often provide a unique blend of comfort and access to outdoor activities, making them ideal for winter sports enthusiasts.

The region is also known for its stunning natural beauty, including Deep Creek Lake, which is just a stone's throw away, offering opportunities for snowshoeing and ice fishing during the winter months.
What is the most popular type of holiday rental accomodation in Oakland?
In Oakland, holiday houses dominate the holiday rental scene, with approximately 1,420 available throughout the area. These properties are typically spacious and well-equipped, featuring multiple bedrooms, full kitchens, and generous living areas, making them ideal for families or larger groups. Many also come with outdoor spaces such as decks or gardens, superb for enjoying the scenic views of Deep Creek Lake and the surrounding mountains.

Cottages are another popular option, with around 368 located in quaint neighbourhoods, often offering a charming and rustic atmosphere. These rentals usually include cosy interiors and basic amenities, providing a comfortable yet simple retreat.

Cabins, of which there are about 292, offer a quintessential experience for those looking to immerse themselves in nature. These often come with wood-burning stoves and are situated in more secluded areas, allowing guests to fully appreciate the natural beauty of the region.

Condos, numbering around 188, provide a more modern accommodation option, typically featuring amenities like pools and fitness centres, and are conveniently located near local attractions. Lastly, there are about 52 chalets that offer a unique, upscale experience with luxurious touches and often stunning views.
Are there any family house rentals in Oakland?
In Oakland, Maryland, there are numerous family-friendly holiday rentals available, with around 431 options to choose from. This charming area is known for its beautiful scenery and proximity to outdoor activities, making it ideal for families. Many properties feature spacious living areas, fully equipped kitchens, and outdoor spaces superb for children to enjoy. You can often find amenities like game rooms, private decks, and fire pits, enhancing the overall experience for families.

The locale is close to Deep Creek Lake, where families can partake in water activities, hiking, and picnicking, while the nearby Wisp Resort offers seasonal adventures for skiing and mountain biking.
Can I rent a holiday home with a pool or hot tub in Oakland?
In Oakland, Maryland, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 145 options to choose from. This charming town, situated near Deep Creek Lake, offers a variety of properties that cater to those looking for relaxation and fun. Many rentals come equipped with private pools, hot tubs, spacious outdoor decks, and fully equipped kitchens, making them ideal for family gatherings or group retreats.

Travellers can find homes in scenic areas close to the lake, where stunning views and access to outdoor activities like boating, fishing, and hiking are just a stone's throw away. Additional amenities often include game rooms, fire pits, and comfortable living spaces, ensuring a delightful stay.
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, providing a variety of options for travellers. Many of these rentals come equipped with amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces, great for families or groups looking to enjoy a comfortable stay.

The area is known for its proximity to Deep Creek Lake, where visitors can indulge in a range of outdoor activities, including hiking, fishing, and boating. Additionally, the nearby state parks offer great opportunities for pet-friendly outings, allowing you to explore scenic trails and enjoy nature with your furry companions.
Are there any remote work holiday rentals in Oakland?
In Oakland, Maryland, there are numerous remote work holiday rentals available, with around 2,248 options to choose from. This picturesque area, located in the foothills of the Appalachian Mountains and near Deep Creek Lake, provides a serene backdrop for those looking to blend work and leisure. Many properties come equipped with reliable Wi-Fi, allowing for seamless connectivity, while some also feature dedicated laptop workspaces to enhance productivity.

Travellers can expect a range of amenities, including comfortable living areas, fully equipped kitchens for preparing meals, and outdoor spaces great for unwinding after a day of work. The proximity to local attractions, such as state parks and recreational activities around the lake, adds to the appeal, offering opportunities for relaxation and exploration during downtime. 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 variety of desirable amenities that enhance the guest experience. Most properties include kitchens, allowing travellers to prepare their own meals, while many also boast inviting fireplaces, great for cosy evenings. For relaxation, hot tubs are a popular amenity, providing a soothing retreat after a day of exploring the area. Onsite parking is typically available, making it convenient for those travelling by car. Additionally, many rentals come equipped with coffee and tea makers, ensuring guests can enjoy their favourite brews at any time.
When is the best time to visit Oakland for a holiday rental?
The best time to book a holiday rental in Oakland is during the summer months, particularly in July, when the town comes alive with vibrant activities and events. This peak season, running from July to September, is great for families and outdoor enthusiasts eager to engage in a variety of recreational pursuits. With temperatures typically ranging from 20 to 30 degrees Celsius, the warm weather invites visitors to explore the stunning natural beauty of the surrounding area.

July is especially popular, as it offers a lively option filled with festivals, outdoor concerts, and numerous water sports on Deep Creek Lake. This month is ideal for those seeking both adventure and community engagement, with ample opportunities for hiking, boating, and enjoying the picturesque scenery.

For travellers looking for a more budget-friendly experience, visiting in December can be a great option. While this month is outside the peak season, it offers a unique charm with the festive holiday decorations and a quieter pace, allowing for relaxed exploration of the area's winter activities.

Ultimately, the best time to visit Oakland depends on your preferences.
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 enjoy a range of attractions that highlight the area's natural beauty and recreational opportunities. Deep Creek Lake is a major draw, offering activities such as boating, fishing, and swimming during the warmer months, alongside picturesque views and hiking trails around the shoreline. The nearby Wisp Resort provides options for skiing and snowboarding in the winter, making it a popular destination for outdoor enthusiasts year-round.

For those interested in history, the Oakland Museum showcases local heritage and culture, while the historic downtown area features charming shops and eateries that reflect the town's small-town atmosphere. Additionally, the scenic beauty of Swallow Falls State Park, with its stunning waterfalls and hiking trails, is easily accessible and great for nature lovers looking to explore the great outdoors.
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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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