Oakland, MD Vacation Rentals

Our Favorite Vacation Rentals in Oakland

  • Still Meadows
    GoodCountry House
    Booking.com
    From
    $99
  • Divided Sky
     5br Home/Apartment
    HolidayLettings
    From
    $414
  • Lake Haven
     Country House
    Booking.com
    From
    $215
  • Cabin in the Woods
    Excellent2br Cabin
    HolidayLettings
    From
    $291
  • The Quarterdeck Four-Bedroom Holiday Home
     Country House
    Booking.com
    From
    $416
  • Cozy Cabin
     4br Cabin
    HolidayLettings
    From
    $384
  • Skydance Five-Bedroom Holiday Home
     Country House
    Booking.com
    From
    $495
  • Schmidt Lodge
     3br Home/Apartment
    HolidayLettings
    From
    $284

Check prices for these upcoming dates

Oakland Vacation Rentals with a Pool

  • Chalet w/indoor pool EV Charger Alpine Lake Resort
    Excellent2br Home/Apartment
    Airbnb
    From
    $239

Oakland Vacation Rentals with Wi-Fi

  • Mountain Lake Corner LLC
    ExcellentHome/Apartment
    Airbnb
    From
    $78
  • Escape to a luxury cabin home on a private lake..
    Excellent4br Home/Apartment
    Airbnb
    From
    $305
  • Haley Farm mountain retreat w/fire pit, jacuzzi tubs, fireplaces, and free WiFi!
     7br Home/Apartment
    Airbnb
    From
    $1,487
  • Dancing Bears
    Excellent3br Home/Apartment
    Airbnb
    From
    $288

Oakland Pet-Friendly Vacation Rentals

  • Red Run Cabin
    Excellent3br Cabin
    HolidayLettings
    From
    $272
  • NEW LISTING! Spacious, waterfront home w/ pool table & shuffleboard - dogs OK!
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $555
  • Charming lake house w/ private hot tub & great views from the deck - dogs OK!
     4br Home/Apartment
    HolidayLettings
    From
    $385
  • Lakefront cabin w/ private dock, hot tub, & game room - dogs okay!
     3br Home/Apartment
    HolidayLettings
    From
    $459

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
82 º46
4
77 º28
0
70 º14
0
59 º14
0
59 º-6
0
72 º5
0
66 º14
0
81 º19
0
79 º45
0
81 º41
0
82 º50
0
81 º46
0
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Oakland. The warmest months in Oakland are April and June, when temperatures reach 82 ˚F. The coolest month is December, when temperatures drop to -6 ˚F. The wettest month in Oakland is April with 3.57 inches of rain, while the driest month is December with 0.04 inches of rain.

What Expert Travelers Think

  • — I use and I recommend AllTheRooms because it is a complete platform. It helps to save a lot of time, it gives all the main information about price, location, and features. In a few steps, I can easily find the best place to stay according to my criteria.

    My Anasa
    My AnasaMy Anasa
  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School

Vacation Rentals in Oakland

Browse vacation rentals from all your favorite providers including Airbnb, Priceline, Bed and Breakfast and many more at AllTheRooms.com. AllTheRooms has 2,160 rentals, hotels and other great places to stay during your time in Oakland, with everything from inexpensive hostels and homestays to luxury Airbnbs and hotels. On average, a place to stay in Oakland will cost you $302 per night.

If you want to stay connected during your trip, then you can choose from over 622 accommodations in Oakland that have WiFi. 3 places to stay include a morning meal. Fitness fanatics can get a workout in during their stay by choosing from 56 accommodations that have gym facilities. Driving to Oakland? Then choose one of the 542 places to stay that comes with a parking spot included. We track 40 places to stay that have a pool or jacuzzi.

AllTheRooms has 136 pet-friendly places to stay in Oakland, so if you're traveling with your cat or dog you won't have any trouble.

700 of the places to stay in Oakland have been rated by previous guests. They rated 31% as excellent or good. 1,055 places to stay in are instantly bookable.

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