Oakland Vacation Rentals

Compare 1,404 available properties from 15 providers
Oakland
Anytime
2 guests
Save up to 45%

Best Vacation Home Deals in Oakland

-39%
e.g. 3/30 - 4/6
House ∙ 8 guests ∙ 3 bedrooms
Oakland, West Oakland, Maryland, United States
from $168 $273
VRBO
5.0
View deal
-43%
e.g. 5/11 - 5/18
House ∙ 6 guests ∙ 2 bedrooms
Oakland, West Oakland, Maryland, United States
from $175 $309
VRBO
4.8
View deal
-45%
e.g. 4/6 - 4/13
House ∙ 8 guests ∙ 2 bedrooms
Oakland, West Oakland, Maryland, United States
from $200 $366
VRBO
4.2
View deal

Book a dreamlike vacation home from $49 per night by searching among the 1,404 properties listed in Oakland. Every one of the accommodations from the different providers are instantaneously compared on our website so you can save up to 39%.

Recommended Vacation Rentals in Oakland

Find your perfect vacation rental in Oakland: from $49 per night

House ∙ 10 guests ∙ 4 bedrooms
Oakland, West Oakland, Maryland, United States
from $352
VRBO
5.0
View deal
House ∙ 8 guests ∙ 3 bedrooms
Oakland, West Oakland, Maryland, United States
from $270
VRBO
5.0
View deal
House ∙ 4 guests ∙ 1 bedroom
Oakland, West Oakland, Maryland, United States
from $99
VRBO
4.7
View deal
House ∙ 6 guests ∙ 3 bedrooms
Oakland, West Oakland, Maryland, United States
from $108
VRBO
4.7
View deal
-11%
Motel ∙ 4 guests
Oakland, West Oakland, Maryland, United States
from $85 $96
Orbitz.com
4.4
View deal
Apartment ∙ 3 guests ∙ 1 bedroom
Oakland, West Oakland, Maryland, United States
from $39
Airbnb
4.5
View deal
Cabin ∙ 2 guests ∙ 1 bedroom
Oakland, West Oakland, Maryland, United States
from $93
Airbnb
5.0
View deal
House ∙ 6 guests ∙ 2 bedrooms
Oakland, West Oakland, Maryland, United States
from $187
VRBO
4.6
View deal
Cabin ∙ 4 guests ∙ 1 bedroom
Oakland, West Oakland, Maryland, United States
from $77
Airbnb
5.0
View deal
See all offers

Vacation Rentals With Fireplaces

Fireplace
House ∙ 8 guests ∙ 3 bedrooms
Oakland, West Oakland, Maryland, United States
from $168
VRBO
5.0
View deal
Fireplace
House ∙ 8 guests ∙ 3 bedrooms
Oakland, West Oakland, Maryland, United States
from $80
VRBO
4.8
View deal
Fireplace
Cabin ∙ 6 guests ∙ 2 bedrooms
Oakland, West Oakland, Maryland, United States
from $119
Airbnb
5.0
View deal
See all offers

Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 8 guests ∙ 4 bedrooms
Oakland, West Oakland, Maryland, United States
from $387
VRBO
4.8
View deal
Fishing
House ∙ 9 guests ∙ 4 bedrooms
Oakland, West Oakland, Maryland, United States
from $379
VRBO
5.0
View deal
Fishing
House ∙ 8 guests ∙ 2 bedrooms
Oakland, West Oakland, Maryland, United States
from $290
VRBO
4.9
View deal
See all offers

Dog-Friendly Vacation Rentals

Pet-friendly
House ∙ 10 guests ∙ 3 bedrooms
Oakland, West Oakland, Maryland, United States
from $562
VRBO
4.5
View deal
Pet-friendly
Cabin ∙ 2 guests ∙ 1 bedroom
Oakland, West Oakland, Maryland, United States
from $93
Airbnb
5.0
View deal
Pet-friendly
Apartment ∙ 4 guests ∙ 1 bedroom
Oakland, West Oakland, Maryland, United States
from $139
Booking.com
5.0
View deal
See all offers

Popular Rental Amenities in Oakland

  • Kitchen (1,240)
  • Internet (1,180)
  • TV (1,029)
  • Fireplace (926)
  • AC (898)
  • No smoking (785)
  • Grill (620)
  • Washer (594)
  • Jacuzzi (519)
  • No pets (440)
  • Parking (435)
  • Microwave (414)
Our search page's filters will help you find the ideal accommodation in Oakland. Oakland is the perfect place to book a property if you can't imagine a vacation without internet or you want to tune out with some TV time, as the most common features are "internet" and "TVs." You can even find properties if you are looking for a pet-friendly rental (1 rentals include "Pets Allowed" in Oakland) or if you want to hang out and relax outside (1 rentals in Oakland include "yards").

The Weather in Oakland

34°
19°
34°
19°
45°
28°
57°
37°
64°
48°
72°
55°
75°
61°
73°
59°
68°
52°
55°
41°
45°
30°
39°
28°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

The above is a climate diagram for Oakland. During July, maximum temperatures go up to more than 75° On the contrary, the coolest month is January. The rainiest month is July while the driest month is January.

Accommodations in Oakland

In Oakland, house rentals are the most typical property type. Additionally, they have an average size of 2,100 ft² as well as a median price of $629 per night. Furthermore, these properties are optimal for 12 it represents the average number of vacationers house rentals can accommodate in Oakland. If you would prefer to compare a different accommodation type, you may want to consider hotel rooms, which are the other most typical accommodation option in Oakland. While house rentals in Oakland have an average size of 2,100 ft², hotel rooms have an average size of 500 ft².

Your vacation home in Oakland awaits you!

If you enjoy falling asleep under the stars between the trees along with a campfire, and yet don't want to give up your comfort of home, you will be pleased with the mountain cabins in Oakland. After a joyful trekking at the Garret State Forest, tree cabins will relieve your tiredness and make you feel at home.

Show all 1,404 properties
Art & Culture

Historical Oakland

Although there are various sites to explore in Oakland, there are some things that should not be missed. Listed on National Register of Historic Places, B&O Railroad Museum is one of the oldest structures of Oakland and it is both an educational and atmospheric attraction.

Local Attractions

Activities in Oakland

State parks such as Swallow Falls, located at the Youghiogheny River 9 miles north Oakland, and Deep Creek Lake, located 18 miles south of Route 219, are just two of many attractions where you can discover the nature of the region. Downhill skiing, kayaking, atv renting, and fishing are just some of the unique experiences that you can make in Oakland.

We compare more than 600 providers, including:

Booking.com Vacation Rentals in Oakland VRBO Vacation Rentals in Oakland HomeAway Vacation Rentals in Oakland Airbnb Vacation Rentals in Oakland TripAdvisor Vacation Rentals in Oakland VacationRentals.com Vacation Rentals in Oakland HouseTrip Vacation Rentals in Oakland FlipKey Vacation Rentals in Oakland 9flats.com Vacation Rentals in Oakland VaycayHero Vacation Rentals in Oakland PerfectPlaces.com Vacation Rentals in Oakland Homestay.com Vacation Rentals in Oakland Only-apartments Vacation Rentals in Oakland Interhome Vacation Rentals in Oakland Bedycasa Vacation Rentals in Oakland Novasol Vacation Rentals in Oakland HomeEscape Vacation Rentals in Oakland

Vacation Destinations Near Oakland