Home Vacation Rentals By Owner In Oakland, MD

Showing 500 Of 570 Vacation Rentals
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Exceptional(6)

$447.72

/ Nightly
Condo

Will O' The Wisp: 301D Two Bedroom/Two Bath

Oakland, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(17)

$285.65

/ Nightly
Condo

Will O' The Wisp: 206A Efficiency/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 3

Sleeps
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Exceptional(1)

$362.5

/ Nightly
Condo

Will O' The Wisp: 303D Two Bedroom/Two Bath

Oakland, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$290.5

/ Nightly
Condo

Will O' The Wisp: 304C One Bedroom/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(2)

$542.02

/ Nightly
Condo

Will O' The Wisp: 305E Three Bedroom/Three Bath

Oakland, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(5)

$322.64

/ Nightly
Condo

Will O' The Wisp: 102B One Bedroom/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(34)

$286.85

/ Nightly
Condo

Will O' The Wisp: 203A Efficiency/One Bath

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 3

Sleeps
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Exceptional(6)

$916.6

/ Nightly
Private Vacation Home

Perfect DCL Lake House: Fire Pit, Hot Tub, Dock and More!

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(10)

$530.43

/ Nightly
Private Vacation Home

Lucky 12 | Centrally Located, Lake Access, Hot Tub

Oakland, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(1)

$264.74

/ Nightly
Condo

Suites at Silver Tree: A120 One Bedroom Standard View

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$292.72

/ Nightly
Apart-hotel

Suites at Silver Tree: A121 One Bedroom Lake View

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(4)

$308.66

/ Nightly
Apart-hotel

Suites at Silver Tree: A318 One Bedroom & Loft Standard View

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(6)

$306.18

/ Nightly
Apart-hotel

Suites at Silver Tree: A304 Studio & Loft Standard View

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(4)

$305.01

/ Nightly
Condo

Suites at Silver Tree: A316 Studio & Loft Standard View

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 6

Sleeps
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$317.18

/ Nightly
Condo

Suites at Silver Tree: B204 One Bedroom Lake View

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(1)

$348.28

/ Nightly
Condo

Suites at Silver Tree: B203 One Bedroom & Loft Lake View

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 6

Sleeps
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$317.18

/ Nightly
Apart-hotel

Suites at Silver Tree: B104 One Bedroom Lake View

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(1)

Select Dates for Price
Apart-hotel

Suites at Silver Tree: B106 One Bedroom Standard View

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$318.34

/ Nightly
Apart-hotel

Suites at Silver Tree: B105 One Bedroom Lake View

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(5)

$292.18

/ Nightly
Apart-hotel

Suites at Silver Tree: A310 Studio & Loft Standard View

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(5)

$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(5)

$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(5)

$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(5)

$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(5)

$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(5)

$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(5)

$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(5)

$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(5)

$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(5)

$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