Oakland, MD vacation rentals

Search among 294 available vacation rentals in Oakland from 50+ providers

Check-in
Select date
-
Check-out
Select date
Rooms and Guests2 Guests, 1 Room
Check-in
Select date
-
Check-out
Select date
Rooms and Guests2 Guests, 1 Room
Filter & Sort
View map
Check-in
Select date
-
Check-out
Select date
Rooms and Guests2 Guests, 1 Room
1Filter & Sort
View map
View map
1-20 out of 294
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
4 adults
1 bedroom
2 beds
Map
6.1 mi from City Center
Composed of 1 bedrooms and 1 bathrooms, this villa is set only 0.4 miles from Muddy Creek Falls.
FromUS$ 99 /nightSelect
6 adults
3 bedrooms
4 beds
Map
5.1 mi from City Center
Situated 0.3 miles from Saint John's Episcopal Church, this villa features board games and a play area for kids.
FromUS$ 167 /nightSelect
6 adults
3 bedrooms
3 beds
Map
6.1 mi from City Center
Swallow Falls State Park and Tolliver Falls are located 1.2 miles and 1.1 miles from the Swallow Falls Cabin #4 Oakland respectively.
FromUS$ 153 /nightSelect
Map
8.7 mi from City Center
Composed of 3 bedrooms and 2 bathrooms, this villa is set only 0.7 miles from Trader's Coffee House.
FromUS$ 122 /nightSelect
A314 Studio & Loft Standard ViewApartment
6 adults
1 bedroom
3 beds
Map
8.0 mi from City Center700 yd from City Center
This 52 m² property with a terrace is located within a 25 minutes' walk from Trader's Coffee House.
FromUS$ 95 /nightSelect
206A Efficiency One BathVilla
3 adults
1 bedroom
2 beds
Map
8.3 mi from City Center
This vacation home is a 10-minute drive from Sand Flat Tabernacle and offers horse riding, bowling and mini golf.
FromUS$ 131 /nightSelect
Grandma'S CottageVilla
8 adults
3 bedrooms
4 beds
Map
8.0 mi from City Center800 yd from City Center
Western Trails is 1.5 miles from the Grandma'S Cottage Oakland, while Trader's Coffee House is 10 minutes away by car.
FromUS$ 114 /nightSelect
Swallow Falls Cabin #3Villa
4 adults
2 bedrooms
2 beds
Map
6.1 mi from City Center
Situated 0.5 miles from Tolliver Falls, the villa offers hiking, horseback riding and mini golf.
FromUS$ 111 /nightSelect
Jamesons Cabin! 8 Minutes To Wisp, Hottub, Firepit, Pets, Ev ChgrVilla
Map
8.2 mi from City Center
Smiley's Fun Zone and Deep Creek Lake are located 1.1 miles and 1.9 miles from the Unwind At Jamesons Cabin! Ev Cgr, Pets, Hottub! Oakland respectively.
FromUS$ 685 /nightSelect
A208 One Bedroom Standard ViewApartment
4 adults
1 bedroom
2 beds
Map
8.0 mi from City Center700 yd from City Center
This 45 m² accommodation consists of 1 bedrooms, a kitchenette and 1 bathrooms.
FromUS$ 124 /nightSelect
Cubs Den - Hot Tub- Walk To Lake- Fire Pit - KayaksVilla
Map
8.8 mi from City Center
Lodestone Golf Club is within 2 miles of the Cubs Den - Hot Tub- Walk To Lake- Fire Pit - Kayaks Oakland and Western Trails is around 2.3 miles away.
FromUS$ 181 /nightSelect
IncognitoVilla
8 adults
3 bedrooms
5 beds
Map
8.6 mi from City Center
While staying at the Incognito you are invited to discover Funland, set around 2.8 miles away, or Arrowhead Market, which is 1.7 miles away.
FromUS$ 180 /nightSelect
A310 Studio & Loft Standard ViewApartment
6 adults
1 bedroom
3 beds
Map
8.0 mi from City Center700 yd from City Center
Western Trails is about 10 minutes' drive away and Deep Creek Lake Discovery Center can be reached within 5 minutes by car.
FromUS$ 181 /nightSelect
A306 Studio & Loft Standard ViewApartment
6 adults
1 bedroom
3 beds
Map
8.0 mi from City Center700 yd from City Center
Deep Creek Lake State Park is around 25 minutes' stroll from the A306 Studio & Loft Standard View and Sand Flat Plaza is 2 miles away.
FromUS$ 118 /nightSelect
A118 Studio Standard ViewApartment
4 adults
1 bedroom
2 beds
Map
8.0 mi from City Center700 yd from City Center
Deep Creek Lake is about a 15-minute walk from the A118 Studio Standard View Oakland and Deep Creek Lake Discovery Center is 1.4 miles away.
FromUS$ 150 /nightSelect
709H Studio Loft One BathVilla
4 adults
1 bedroom
2 beds
Map
8.3 mi from City Center
Set within walking distance of Splash Island at Will O' the Wisp, this vacation home includes 1 bedrooms and a kitchen for guests' convenience.
FromUS$ 193 /nightSelect
Nature'S EscapeVilla
4 adults
1 bedroom
2 beds
Map
6.1 mi from City Center
Set within walking distance of Muddy Creek Falls, this villa includes 1 bedrooms and an equipped kitchen for guests' convenience.
FromUS$ 101 /nightSelect
Deep Creek Lake Townhome With Deck And Water ViewsVilla
6 adults
2 bedrooms
2 beds
Map
8.8 mi from City Center
The Deep Creek Lake Townhome With Deck And Water Views is set 2.1 miles from Deep Creek Lake State Park and within 2.2 miles of Deep Creek Lake Discovery Center.
FromUS$ 215 /nightSelect
Owl'S NestVilla
8 adults
5 bedrooms
5 beds
Map
8.7 mi from City Center
Garrett Lakes Arts Festival and Deep Creek Lake State Park are located 2.8 miles and 2.1 miles from the Owl'S Nest Oakland respectively.
FromUS$ 257 /nightSelect
202B One Bedroom One BathVilla
4 adults
1 bedroom
2 beds
Map
8.3 mi from City Center
Splash Island at Will O' the Wisp is a mere 100 feet from the 202B One Bedroom One Bath Oakland, while Smiley's Fun Zone is 1.5 miles away.
Select
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9
  • 10
  • 15

Oakland vacation rentals

Handpicked vacation rentals in Oakland

If you're traveling with your family, consider rent an apartment in Oakland to make the most of your journey. Traveling to Oakland with your family? Consider booking a vacation rental next to Adventure Sports Center International. Check these magnificent accommodations and reserve the one you liked!

Exclusive luxury places to stay in Oakland

It is Oakland that attracts visitors with the opulent atmosphere of local vacation homes. Not just another boring vacation, but a fantastic adventure awaits you. You can entrust us to find the classiest vacation rentals in Oakland, we will never disappoint you!

High graded cheap vacation homes in Oakland

More expensive is not necessarily better. Cheap vacation apartments in Oakland start at 235US$ per night, as well as it is possible to find a budget villa for 104US$. Our team has reviewed available dates in United States from 100+ providers and picked a selection of cheap vacation homes in Oakland. Find out more!

Show moreLess

Vacation rentals in Oakland essential information

🏨 Vacation rentals in Oakland 294
👛 Lowest price 93 USD