Oakland, MD Vacation Rentals

Our Favorite Vacation Rentals in Oakland

The Herrington
Nice
HolidayLettingsFrom $2661
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Ski Solitude
Excellent
HolidayLettingsFrom $268
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Swallow Falls Cabin 3
Excellent
HolidayLettingsFrom $217
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Red Run Cabin
Excellent
HolidayLettingsFrom $286
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It's 5 O'Clock Somewhere
Good
HolidayLettingsFrom $466
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Glistening Waters
Excellent
HolidayLettingsFrom $530
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Making Memories
Excellent
HolidayLettingsFrom $709
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Pine Oasis
Good
HolidayLettingsFrom $593
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Oakland Vacation Rentals with a Pool

Lake View Chalet in Alpine Lake Resort
Excellent
AirbnbFrom $374
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Chalet w/indoor pool at Alpine Lake Resort
Excellent
AirbnbFrom $231
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Ski Harbor #45
Nice
AirbnbFrom $268
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Oakland Vacation Rentals with Wi-Fi

Large 2-bdrm apt. Walking distance to everything
Excellent
AirbnbFrom $78
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Mountain Lake Corner LLC
Excellent
AirbnbFrom $55
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Dancing Bears
Excellent
AirbnbFrom $263
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Cozy Cabin @ Deep Creek Lake
Excellent
AirbnbFrom $258
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Oakland Pet-Friendly Vacation Rentals

Willow Point
Nice
HolidayLettingsFrom $334
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Majestic Lodge
Good
HolidayLettingsFrom $1208
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Snuggl'Inn
Nice
HolidayLettingsFrom $599
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A Scandinavian Retreat
Nice
HolidayLettingsFrom $415
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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 in Oakland

Most expensive

Most availability

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

SEE FULL WEATHER FORECAST:

81º 19º

79º 45º

81º 41º

82º 50º

59º -6º

0.04

82º 46º

3.57

77º 28º

0.3

70º 14º

59º -6º

0.04

59º -6º

0.04

72º 5º

66º 14º

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Jan

Feb

Mar

Rainy days

SEE FULL WEATHER FORECAST:

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

— Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location
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The Life of a Social Butterfly
— I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.
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— AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from
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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.