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Oakland, MD Vacation Rentals

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Our Favorite Vacation Rentals in Oakland

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Oakland Vacation Rentals with a Pool

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Oakland Vacation Rentals with Wi-Fi

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Oakland Pet-Friendly Vacation Rentals

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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 Index 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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70º 14º
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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.

Vacation Rentals in Oakland

Browse accommodations from all the best providers including Airbnb, VRBO, Glamping Hub and more at AllTheRooms.com. Oakland has 1,842 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. The average price of accommodation in is $342 per night.

Those looking to get some work done during their trip to Oakland can pick from 528 places to stay that provide WiFi. 4 of our accommodations in include a breakfast in the price. Fitness addicts can get a workout in during their stay by choosing from 9 accommodations that have gym facilities. Driving to Oakland? Then choose one of the 468 places to stay that comes with a parking spot included. We have 45 places to stay that have a pool or jacuzzi.

If you're traveling with a furry friend, then be sure to choose one of the 138 pet-friendly accommodations available.

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 406 places to stay from Airbnb, 150 accommodations from VRBO and 16 places to stay from Glamping Hub.

554 accommodations in Oakland have been reviewed: 28% are rated excellent or good. 950 places to stay in are instantly bookable.

Destinations near Oakland

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