Oakland, MD Vacation Rentals

Our Favorite Vacation Rentals in Oakland

  • Lake Haven
     Country House
    Booking.com
    From
    $260
  • The Herrington
    Nice10br Home/Apartment
    HolidayLettings
    From
    $3,391
  • Still Meadows
     Country House
    Booking.com
    From
    $99
  • Schmidt Lodge
     3br Home/Apartment
    HolidayLettings
    From
    $331
  • Knotty Pines Three-Bedroom Holiday Home
     Country House
    Booking.com
    From
    $212
  • Hideaway - Picturesque 2 Bedroom Cottage
     2br Home/Apartment
    HolidayLettings
    From
    $187
  • Lakeview Cottage Three-Bedroom Holiday Home
     Country House
    Booking.com
    From
    $206
  • Swallow Falls Cabin 3
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $270

Check prices for these upcoming dates

Oakland Vacation Rentals with a Pool

  • Millstone Cottage
     2br Home/Apartment
    Airbnb
    From
    $164
  • Chalet w/indoor pool EV Charger Alpine Lake Resort
    Excellent2br Home/Apartment
    Airbnb
    From
    $267
  • Lake access home just minutes from Wisp Resort, includes hot tub & fireplaces!
     5br Home/Apartment
    Airbnb
    From
    $898
  • Town home w/ breathtaking mountain views, hot tub, & private home theater!
     4br Home/Apartment
    Airbnb
    From
    $618

Oakland Vacation Rentals with Wi-Fi

  • Large 2-bdrm apt. Walking distance to everything
    Excellent2br Home/Apartment
    Airbnb
    From
    $151
  • Mountain Lake Park Getaway (Cleaning included!)
    ExcellentHome/Apartment
    Airbnb
    From
    $134
  • Dog friendly home minutes from Swallow Falls State park w/ hot tub!
     3br Home/Apartment
    Airbnb
    From
    $502
  • Pet friendlyTerra Alta Lake Farm
    ExcellentHome/Apartment
    Airbnb
    From
    $62

Oakland Pet-Friendly Vacation Rentals

  • Lakefront cabin w/ private dock, hot tub, & game room - dogs okay!
     3br Home/Apartment
    HolidayLettings
    From
    $425
  • Fox Den at Deep Creek
    Good3br Home/Apartment
    Airbnb
    From
    $343
  • FINALLY SETTLED: Lake Access/Hot Tub/Pet Friendly
    Excellent4br Home/Apartment
    Airbnb
    From
    $570
  • Beautiful Adventure
     3br Home/Apartment
    Airbnb
    From
    $360

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
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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
70° 14°
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59° -6°
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66° 14°
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81° 19°
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79° 45°
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81° 41°
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82° 50°
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81° 46°
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82° 46°
4
77° 28°
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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

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Vacation Rentals in Oakland

Browse accommodations from all the best providers including Airbnb, Priceline, Bed and Breakfast and many more at AllTheRooms.com. AllTheRooms has 2,313 rentals, hotels and other great places to stay during your time in Oakland, with everything from inexpensive hostels and homestays to extravagant Airbnbs and hotels. An average vacation rental in Oakland costs on average $304 a night.

If you have to have an internet connection during your time in Oakland, then you can choose from over 519 accommodations that provide WiFi internet. 3 of our accommodations include a breakfast in the price. Choose from 51 accommodations that provide gym options, so you won't miss a single workout. Driving to Oakland? Then choose one of the 380 places to stay that comes with a parking spot included. 40 vacation rentals have a a pool or jacuzzi

AllTheRooms has 145 pet-friendly places to stay in Oakland, so if you're traveling with your pet you won't have any trouble.

745 accommodations in Oakland have been reviewed; 34% are rated excellent or good. 1,180 places to stay in are instantly bookable.

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