Home Vacation Home Rentals By Owner In Oakland, MD

Showing 180 Of 372 Vacation Rentals
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Exceptional(10)

$880.93

/ Nightly
Private Vacation Home

Foxcroft: Lake Access, Hot Tub, Game Room, Pool Table, Dogs OK

Oakland, Maryland, United States

Bed 5

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(81)

$881

/ Nightly
Private Vacation Home

Claralea Lodge | Secluded, Lakefront, Private Dock

Oakland, Maryland, United States

Bed 5

Bed

Bath 5

Bath

Sleep 12

Sleeps
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Exceptional(48)

$892.24

/ Nightly
Private Vacation Home

Luxury Dog Friendly Escape w/ Hot Tub & Views

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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$939.7

/ Nightly
Private Vacation Home

Luxury 4BR Mansion - HOT TUB - Lake View - Oakland

Oakland, Maryland, United States

Bed 4

Bed

Bath 5

Bath

Sleep 12

Sleeps
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Exceptional(5)

$1027.9

/ Nightly
Private Vacation Home

Modern Lakehouse w/ Dock, Fire Pit, Hot Tub

OAKLAND, Maryland, United States

Bed 6

Bed

Bath 5

Bath

Sleep 15

Sleeps
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Exceptional(4)

$1026.51

/ Nightly
Private Vacation Home

7BR Deep Creek Lodge w/ Fire Pit & Views

Oakland, Maryland, United States

Bed 7

Bed

Bath 6

Bath

Sleep 16

Sleeps
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$1020.71

/ Nightly
Private Vacation Home

New! Charming Lakefront w/ Dock & Mountain Views

Oakland, Maryland, United States

Bed 5

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(14)

$998.23

/ Nightly
Private Vacation Home

Signature Lakefront w/ Dock & Pool Table

OAKLAND, Maryland, United States

Bed 7

Bed

Bath 6

Bath

Sleep 22

Sleeps
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Exceptional(5)

$991.98

/ Nightly
Private Vacation Home

Modern Dog Friendly Mountain Retreat w/ Hot Tub

Oakland, Maryland, United States

Bed 6

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(2)

$991.85

/ Nightly
Private Vacation Home

Dog Friendly Deep Creek Estate w/ Fire Pit & Views

Oakland, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 14

Sleeps
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Exceptional(17)

$979.36

/ Nightly
Private Vacation Home

Huge + Quiet + Hot Tub + Theatre Room

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(9)

$959.79

/ Nightly
Private Vacation Home

Elegant Lakefront Retreat w/ Hot Tub & Fireplaces

Oakland, Maryland, United States

Bed 5

Bed

Bath 5

Bath

Sleep 10

Sleeps
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Exceptional(4)

$952.41

/ Nightly
Private Vacation Home

Beautiful 65 Acre Farm with Wrap Around Porch

Oakland, Maryland, United States

Bed 6

Bed

Bath 6

Bath

Sleep 12

Sleeps
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Exceptional(4)

$945.69

/ Nightly
Private Vacation Home

Bear on the Lake | Boat Dock, Hot Tub, Fire Pit

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(2)

$942.34

/ Nightly
Private Vacation Home

Treeline Lodge | Walk to Honi + Lakefront + Tiki Bar Vibes

Oakland, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(79)

$905.24

/ Nightly
Private Vacation Home

Bear Hollow Lodge | Pet-Friendly, Boat Dock, Hot Tub

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(4)

$911.26

/ Nightly
Private Vacation Home

Stylish Lakefront Home w/ Foosball & Hot Tub

Oakland, Maryland, United States

Bed 5

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(4)

$907.75

/ Nightly
Private Vacation Home

Serene Lakefront Chalet w/ Dock Hot Tub & Fire Pit

Oakland, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(4)

$912.92

/ Nightly
Private Vacation Home

Johnny Appleseed | Lakefront, Hot Tub, Private Dock

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(2)

$902.17

/ Nightly
Private Vacation Home

Lake Days & Game Nights w/ Hot Tub

Oakland, Maryland, United States

Bed 5

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Home Most popular vacation rentals in Oakland

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Exceptional(2)

$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(2)

$719.68

/ 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(2)

$719.97

/ 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(2)

$724.63

/ Nightly
Private vacation home

Stone Haven: Sauna, Lake Access, 4 Suites, Hot Tub

Oakland, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 10

Sleeps
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Exceptional(2)

$725.89

/ 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(2)

$732.77

/ 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(2)

$735.39

/ 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(2)

$756.84

/ Nightly
Cabin

Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger!

Oakland, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(2)

$756.69

/ Nightly
Private vacation home

Wooded Tranquil Retreat w/ Hot Tub & Fireplace

Oakland, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(2)

$746.39

/ Nightly
Private vacation home

Relaxing Lakefront in Prime Location w/Lake Access

Oakland, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 11

Sleeps

Most Popular Cities in Maryland