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Oakland, MD Vacation Rentals

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Our Favorite Vacation Rentals in Oakland

  • Still Meadows
    Still Meadows
     
    Booking.comFrom $113
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  • Cozy Lake Cabin
    Cozy Lake Cabin
    Excellent
    HolidayLettingsFrom $268
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  • Bear Necessity's
    Bear Necessity's
     
    Booking.comFrom $272
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  • Swallow Falls Cabin 3
    Swallow Falls Cabin 3
    Excellent
    HolidayLettingsFrom $266
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  • Chalet in Hiding
    Chalet in Hiding
     
    Booking.comFrom $350
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  • NEW LISTING! Spacious home w/convenient location & hot tub, near lake & dining
    NEW LISTING! Spacious home w/convenient location & hot tub, near lake & dining
     
    HolidayLettingsFrom $439
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  • 29 Aker Wood
    29 Aker Wood
     
    Booking.comFrom $253
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  • Charming cabin w/ split lake access dock, & firepit at the water's edge
    Charming cabin w/ split lake access dock, & firepit at the water's edge
     
    HolidayLettingsFrom $453
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See all 1,918 deals in Oakland

Oakland Vacation Rentals with Wi-Fi

  • Charming 1-bdrm with balcony, close to everything
    Charming 1-bdrm with balcony, close to everything
    Good
    AirbnbFrom $78
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  • Mountain Lake Park Getaway (Cleaning included!)
    Mountain Lake Park Getaway (Cleaning included!)
    Excellent
    AirbnbFrom $122
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  • Forest Ridge @ Deep Creek Lake
    Forest Ridge @ Deep Creek Lake
    Excellent
    AirbnbFrom $479
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  • Haley Farm getaway w/ firepit, multiple jetted tubs, fireplaces & large deck!
    Haley Farm getaway w/ firepit, multiple jetted tubs, fireplaces & large deck!
     
    AirbnbFrom $1573
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See all deals in Oakland with WiFis

Oakland Pet-Friendly Vacation Rentals

  • Cozy condo w/amazing lake view in great location & dog friendly!
    Cozy condo w/amazing lake view in great location & dog friendly!
     
    HolidayLettingsFrom $261
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  • Large chalet w/hot tub, jetted tub, tennis, & golf - dogs OK
    Large chalet w/hot tub, jetted tub, tennis, & golf - dogs OK
     
    HolidayLettingsFrom $549
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  • Dog-friendly country cabin w/ deck, firepit & air hockey - close to Yough River!
    Dog-friendly country cabin w/ deck, firepit & air hockey - close to Yough River!
     
    HolidayLettingsFrom $232
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  • Lake access chalet-style home w/ 2 furnished patios, & private hot tub - dogs OK
    Lake access chalet-style home w/ 2 furnished patios, & private hot tub - dogs OK
     
    HolidayLettingsFrom $613
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See all deals in Oakland that allow pets

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

81º 41º
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82º 50º
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81º 46º
0.12
82º 46º
3.57
77º 28º
0.3
70º 14º
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59º 14º
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59º -6º
0.04
72º 5º
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66º 14º
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81º 19º
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79º 45º
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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.

Destinations near Oakland