Oakland Vacation Rentals | Book Now, Save Up to 30%

All in pricing: Taxes and fees included

Save $141

Guests rave

House in Oakland, MD

Nov 16 - 19

$495/night

5.0

24

4 bedrooms

10 guests

$1,757$1,617total

Save $358

Guests rave

House in Oakland, MD

Nov 16 - 19

$360/night

5.0

76

3 bedrooms

7 guests

$1,533$1,175total

Save $105

Unit 1 of 2

Camper/RV in Oakland, MD

Nov 20 - 23

$133/night

New

1 bedroom

4 guests

$525$419total

Save $142

House in Oakland, MD

Nov 16 - 19

$500/night

5.0

18

4 bedrooms

10 guests

$1,774$1,632total

Save $155

Guests rave

House in Oakland, MD

Nov 16 - 19

$495/night

5.0

23

4 bedrooms

10 guests

$1,771$1,616total

Save $160

House in Oakland, MD

Nov 29 - Dec 2

$475/night

5.0

18

3 bedrooms

7 guests

$1,725$1,565total

Save $150

Guests rave

House in Oakland, MD

Nov 16 - 19

$532/night

5.0

23

5 bedrooms

14 guests

$1,878$1,727total

Save $558

Unit 2 of 2

Castle in Oakland, MD

Nov 28 - Dec 1

$646/night

4.6

11

7 bedrooms

16 guests

$2,602$2,044total

Save $67

Preferred host

Entire townhouse in Oakland, MD

Nov 16 - 19

$228/night

4.8

13

2 bedrooms

6 guests

$835$768total

Save $167

Guests rave

House in Oakland, MD

Nov 16 - 19

$588/night

5.0

47

5 bedrooms

14 guests

$2,087$1,920total

Save $113

Preferred host

Entire townhouse in Oakland, MD

Apr 16 - 19

$248/night

5.0

4

2 bedrooms

8 guests

Pay only $94 today

$946$833total

Save $180

Guests rave

House in Oakland, MD

Nov 16 - 19

$495/night

5.0

28

4 bedrooms

10 guests

$1,797$1,617total

Save $89

Preferred host

Entire home in Oakland, MD

Nov 16 - 19

$302/night

5.0

4

3 bedrooms

9 guests

$1,107$1,018total

Save $126

Preferred host

Vacation Rental in Oakland, MD

Nov 16 - 19

$434/night

4.8

57

5 bedrooms

12 guests

$1,571$1,445total

Save $149

Preferred host

Cabin in Oakland, MD

Nov 16 - 19

$378/night

4.9

9

5 bedrooms

14 guests

$1,427$1,278total

Save $143

Guests rave

House in Oakland, MD

Nov 16 - 19

$506/night

5.0

44

4 bedrooms

12 guests

$1,785$1,642total

Save $131

Whimstay gem

Cabin in Terra Alta, WV

Nov 16 - 19

$218/night

4.9

29

2 bedrooms

8 guests

$845$714total

Save $52

Whimstay gem

Cabin in Terra Alta, WV

Nov 16 - 19

$185/night

4.9

75

3 bedrooms

8 guests

$656$603total

Save $71

Preferred host

Entire cabin in Terra Alta, WV

Nov 16 - 19

$246/night

5.0

5

3 bedrooms

8 guests

$886$815total

Save $93

Preferred host

Cabin in Terra Alta, WV

Nov 16 - 19

$323/night

5.0

4

6 bedrooms

13 guests

$1,157$1,064total

Save $84

Preferred host

Cabin in Terra Alta, WV

Nov 16 - 19

$248/night

4.5

19

3 bedrooms

10 guests

$896$812total

View all properties in Oakland

Map shows last minute vacation rentals in Oakland