Oakland, MD Vacation Rentals

Our Favorite Vacation Rentals in Oakland

  • Lake Haven
     Country House
    Booking.com
    From
    $341
  • Cozy Cabin
     4br Cabin
    HolidayLettings
    From
    $531
  • Lake House Four-Bedroom Holiday Home
     Country House
    Booking.com
    From
    $421
  • Schmidt Lodge
     3br Home/Apartment
    HolidayLettings
    From
    $620
  • The Quarterdeck Four-Bedroom Holiday Home
     Country House
    Booking.com
    From
    $602
  • Swallow Falls Cabin 3
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $350
  • Blue Waters Three-Bedroom Holiday Home
     Country House
    Booking.com
    From
    $279
  • An Apple Away
     4br Home/Apartment
    HolidayLettings
    From
    $579

Check prices for these upcoming dates

Oakland Vacation Rentals with a Pool

  • Millstone Cottage at Alpine Lake Resort
    Excellent2br Home/Apartment
    Airbnb
    From
    $171
  • Ruth's Lair Alpine Lake Resort
     3br Home/Apartment
    Airbnb
    From
    $141
  • Bluebell Cottage
     Home/Apartment
    Airbnb
    From
    $226
  • Dog friendly home with private dock, hot tub, pool table and community amenities
     4br Home/Apartment
    Airbnb
    From
    $657

Oakland Vacation Rentals with Wi-Fi

  • 2BR Loft home Oakland Maryland
    Good2br Home/Apartment
    Airbnb
    From
    $109
  • The Perch: Lake Access Chalet Overlooking Deep Creek
     3br Home/Apartment
    Airbnb
    From
    $558
  • Mountain Lake Corner
    ExcellentHome/Apartment
    Airbnb
    From
    $88
  • Blarney Stone Manor @ Deep Creek Lake
    Excellent3br Home/Apartment
    Airbnb
    From
    $475

Oakland Pet-Friendly Vacation Rentals

  • Red Run Cabin
    Excellent3br Cabin
    HolidayLettings
    From
    $344
  • Family- and dog-friendly home w/ deck, forest view - close to lake & ski slopes
    Nice3br Home/Apartment
    HolidayLettings
    From
    $341
  • Dog-friendly lakehouse w/ boat slip, spacious deck, & partial views of the water
     3br Home/Apartment
    HolidayLettings
    From
    $292
  • Memory Lane - House
     4br Home/Apartment
    HolidayLettings
    From
    $410

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
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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 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 Weather in Oakland

Rainy days
54° -11°
1
59°
0
70°
0
77° 19°
0
79° 34°
0
79° 43°
0
82° 52°
1
82° 46°
0
81° 45°
0
81° 30°
0
61°
0
55°
0
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Oakland. The hottest month in Oakland is May, when temperatures peak at 82 ˚F. The coolest month is December, when temperatures drop to -11 ˚F. The wettest month in Oakland is June with 0.95 inches of rain, while the driest month is December with 0.57 inches of rain.

What Expert Travelers Think

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    Samantha Wragg
    Samantha WraggCoco Travels
  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit
  • — 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.

    Alli Sims
    Alli SimsAlli Sims

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