Home Vacation Rentals By Owner In Oakland, MD

Showing 480 Of 570 Vacation Rentals
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Exceptional(4)

$285.65

/ Nightly
Condo

Will O' The Wisp: 106A Efficiency/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 3

Sleeps
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Exceptional(8)

$250.88

/ Nightly
Condo

Will O' The Wisp: 514C One Bedroom/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(18)

$293.12

/ Nightly
Condo

Will O' The Wisp: 706H Studio Loft/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(6)

$247.9

/ Nightly
Condo

Will O' The Wisp: 201B One Bedroom/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(22)

$288.16

/ Nightly
Condo

Will O' The Wisp: 708H Studio Loft/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(12)

$288.16

/ Nightly
Condo

Will O' The Wisp: 103A Efficiency/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(5)

$294.84

/ Nightly
Condo

Will O' The Wisp: 307C One Bedroom/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(17)

$290.5

/ Nightly
Condo

Will O' The Wisp: 306C One Bedroom/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(5)

$432.86

/ Nightly
Condo

Will O' The Wisp: 308D Two Bedroom/Two Bath

Oakland, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(9)

$288.16

/ Nightly
Condo

Will O' The Wisp: 711H Studio Loft/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(2)

$329.84

/ Nightly
Condo

Will O' The Wisp: 309B One Bedroom/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(8)

$288.16

/ Nightly
Condo

Will O' The Wisp: 710H Studio Loft/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(2)

$497.32

/ Nightly
Condo

Will O' The Wisp: 502F Three Bedroom/Two Bath

Oakland, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 12

Sleeps
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Exceptional(2)

$310.75

/ Nightly
Condo

Will O' The Wisp: 104B One Bedroom/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 6

Sleeps
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$504.9

/ Nightly
Condo

Will O' The Wisp: 505F Three Bedroom/Two Bath

Oakland, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 12

Sleeps
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Exceptional(6)

$507.51

/ Nightly
Condo

Will O' The Wisp: 504F Three Bedroom/Two Bath

Oakland, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(26)

$288.97

/ Nightly
Condo

Will O' The Wisp: 105A Efficiency/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 3

Sleeps
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Exceptional(24)

$242.91

/ Nightly
Condo

Will O' The Wisp: 714H Studio Loft/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(6)

$309.58

/ Nightly
Condo

Will O' The Wisp: 207B One Bedroom/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(3)

$318.63

/ Nightly
Condo

Will O' The Wisp: 208B One Bedroom/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Home Most popular vacation rentals in Oakland

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Exceptional(3)

$742.84

/ Nightly
Private vacation home

Dog Friendly Retreat Near Deep Creek w/ Hot Tub!

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 11

Sleeps
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Exceptional(3)

$716.28

/ Nightly
Private vacation home

New! Historic Lake Cottage w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(3)

$731.03

/ Nightly
Private vacation home

New! Woodsy Hideaway w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(3)

$731.28

/ Nightly
Private vacation home

Central Lake House, Private Dock! Walk to Area Hot Spots!

Oakland, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(3)

$738.12

/ Nightly
Private vacation home

Lakefront 5BR retreat with hot tub, game room, and boat slip.

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(3)

$739.25

/ Nightly
Private vacation home

Black Bear Lodge | Lake Access, Shared Indoor Pool

Oakland, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(3)

$740.33

/ Nightly
Private vacation home

Prime Location w Hot tub & Firepit

Oakland, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(3)

$763.19

/ Nightly
Cabin

Secluded Mtn Cabin: 7BR, Pool, Hot Tub, Game Room

Oakland, Maryland, United States

Bed 7

Bed

Bath 4

Bath

Sleep 18

Sleeps
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Exceptional(3)

$762.78

/ Nightly
Private vacation home

Stylish Lakefront Escape w/ Hot Tub, Bar & Dock

Oakland, Maryland, United States

Bed 4

Bed

Bath 5

Bath

Sleep 12

Sleeps
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Exceptional(3)

$758.95

/ Nightly
Private vacation home

Luxury Expansive Lakefront, Newly Renovated!

Oakland, Maryland, United States

Bed 4

Bed

Bath 6

Bath

Sleep 10

Sleeps

Most Popular Cities in Maryland