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Oakland, MD Vacation Rentals

Our Favorite Vacation Rentals in Oakland

Oakland Vacation Rentals with Wi-Fi

Oakland Pet-Friendly 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 January, 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 Monday, while the most expensive day tends to be Saturday. 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 inches of rain.

What Expert Travelers Think

Vacation Rentals in Oakland

Browse vacation rentals from all the best providers including Airbnb, Priceline, Bed and Breakfast and many more at AllTheRooms.com. We have 1,899 vacation rentals, hotels and other accommodation types in Oakland ranging from inexpensive options to luxury places to stay. The average price of a rental is generally $323 per night.

If you would like to stay connected during your vacation, then you can choose from over 584 accommodations in Oakland that have WiFi. 3 of our accommodations include a breakfast in the price. Fitness addicts can get a workout in during their stay by choosing from 56 accommodations that have gym facilities. If you're planning on arriving in Oakland by car, be sure to choose from 515 accommodations that provide parking. We track 40 hotels and vacation rentals that have a pool or jacuzzi.

AllTheRooms has 143 pet-friendly places to stay in Oakland, so if you're traveling with your pet you won't have any trouble.

578 accommodations in Oakland have been reviewed; 27% are rated highly. 886 places to stay in are instantly bookable.