We found 1,223 holiday rentals — enter your dates for availability
Discover a selection of 1,000 holiday rentals in Oakland, MD, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and internet/WiFi. Prices start at £ 149 per night, and cabins and houses are popular options for a stay in Oakland. Either way, you'll find a rental for everyone's needs.
DynamicDestinationRefinements
AsyncDestinationUrgency
Find the best place to stay — Oakland
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
Activities
Sightseeing in and around Oakland
Do you want to discover attractions to visit in the area? Venture out of your holiday home and experience everything that Oakland has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:
- Thousand Acres Lakeside Golf Course (9.3 mi / 14.9 km)
- Wisp Resort (11.7 mi / 18.9 km)
- Hovatter's Wildlife Zoo (20.4 mi / 32.9 km)
- Timberline Four Season Resort (23.9 mi / 38.5 km)
- Canaan Valley Ski Resort (25.6 mi / 41.2 km)
Natural features
Exploring the natural landscape of Oakland
Travellers enjoy Oakland for its lakeside setting and riverfront. Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Oakland is a great place to get out in nature. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:
- Cathedral State Park (8.9 mi / 14.2 km)
- Deep Creek Lake State Park (10.5 mi / 16.8 km)
- Cranesville Swamp Natural Area (11.2 mi / 18 km)
- Fairfax Stone Historical Monument Park (14.5 mi / 23.3 km)
- Big Run State Park (17.2 mi / 27.6 km)
- Blackwater Falls State Park (19.9 mi / 32.1 km)
How to get there
Transport to and around Oakland
Fly into Morgantown, WV (MGW-Morgantown Municipal), the closest airport, located 33.3 mi (53.6 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Elkins, WV (EKN-Randolph County), which is 42.8 mi (68.9 km) away.
Can I find a vacation rental around Oakland?
Yes, our 2021 property listings offer a large selection of 1,223 vacation rentals near Oakland. From 84 cabins to 1,097 houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Oakland for a holiday or a weekend are on Vrbo.
What is the best area to stay when traveling to Oakland?
Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Oakland:
- Blakeslee: 50 vacation rentals
- Paradise Point: 195 vacation rentals
- The View: 167 vacation rentals
- Mountainside: 164 vacation rentals
- Silver Ridge: 207 vacation rentals
For other neighborhoods, please use our search bar to access the selection of vacation rentals available.
Can I rent Cabins in Oakland?
Yes, of course. Vrbo UK has 84 Cabins in Oakland. Our other popular types of vacation rentals in Oakland include:
- Houses: 1,097 rentals available
- Cottages: 84 rentals available
- Flats: 117 rentals available
But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.
Can I find a vacation rental with pool in Oakland?
Yes, you can select your preferred vacation rental with pool among our 184 vacation rentals with pool available in Oakland. Please use our search bar to access the selection of vacation rentals available.