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Oakland, MD Vacation Rentals

Oakland, Maryland Travel Guide

Oakland is a small town in the Western reaches of Maryland, and while it may be sleepy by nature, it's only a car ride away from a variety of locations like Pittsburgh to the north, Morgantown, West Virginia to the west, and Washington DC to the east. With an all-American feel and historic, old buildings lining the main roads, Oakland is a picturesque place to see.

Things to Do in Oakland, Maryland

Oakland is home to a popular railroad museum, outlining its involvement with the B&O Railroad. Oakland is also close to a number of beautiful outdoor destinations like Swallow Falls State Park and Herrington Manor State Park.

Best Time to Visit Oakland, Maryland

Fall is a lovely time to visit as the weather still holds above freezing levels and visitors can admire the changing colors of autumn.

Price and Availability in Oakland

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The most expensive month to stay in a vacation rental in Oakland is in September, while the cheapest month is in October. The most popular time to book a vacation rental in Oakland is in the high season in August. Oakland has its low season in March, when less people are visiting and the vacation home occupancy rate drops.
The cheapest day to stay at a vacation rental in Oakland tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in Oakland tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The Weather in Oakland

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This climate histogram shows you the weather patterns in Oakland. The hottest month in Oakland is June, when temperatures peak at 82 ˚F. The coolest month is January, when temperatures drop to -6 ˚F. The wettest month in Oakland is September with 3.57 inches of rain, while the driest month is December with 0.04 inches of rain.

What Expert Travelers Think

Vacation Rentals in Oakland

Browse accommodations from all the best providers including Airbnb, VRBO, Glamping Hub and more at AllTheRooms.com. We have 1,901 vacation rentals, hotels and other accommodation types in Oakland ranging from budget options to luxury places to stay. The average price of accommodation in is $324 per night.

If you need an internet connection during your stay in Oakland, then you can choose from over 583 places to stay that provide WiFi internet. We have 4 accommodations that come with a breakfast included. You can keep up with your workout regime by staying at one of 56 accommodations that provide gym facilities. If you are driving to Oakland, you'll want to pick from 518 places to stay that provide parking. 40 accommodations come with a pool or jacuzzi

Those traveling with a dog, cat or some other animal can stay in one of 141 accommodations that are designated as pet-friendly.

We combine a wide variety of Oakland accommodations including vacation rentals, homestays, hostels and other unique places to stay into one easy search. We show results from more than 6 providers, including 469 places to stay from Airbnb, 143 accommodations from VRBO and 16 places to stay from Glamping Hub.

577 of our places to stay in Oakland have been rated by previous guests. They rated 27% as excellent or good. 888 accommodations allow instant booking.