Home Vacation Home Rentals By Owner In Oakland, MD

Showing 300 Of 372 Vacation Rentals
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Exceptional(3)

$798.17

/ Nightly
Private Vacation Home

Spacious Lakefront w/ Games & Sunroom

OAKLAND, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 14

Sleeps
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Exceptional(10)

$805.07

/ Nightly
Private Vacation Home

Loch Nest | Lakefront, Private Dock, Dog Friendly!

Oakland, Maryland, United States

Bed 5

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(1)

$808.55

/ Nightly
Private Vacation Home

Nature's Retreat | Private Dock, Community Pool!

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(6)

$815.03

/ Nightly
Private Vacation Home

Amazing Flat Lakefront Home with Hot Tub + Fire Pit!

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(10)

$817.02

/ Nightly
Private Vacation Home

Modern Dog Friendly Cabin w/ Pool & Hot Tub

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(3)

$821.15

/ Nightly
Private Vacation Home

A Lil Slice of Heaven | Pet Friendly, Hot Tub, Billiards

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(3)

$826.84

/ Nightly
Private Vacation Home

Cozy Lakefront Retreat w/Dock, Hot Tub & Fireplace

Oakland, Maryland, United States

Bed 6

Bed

Bath 5

Bath

Sleep 12

Sleeps
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Exceptional(16)

$830.37

/ Nightly
Private Vacation Home

Huge, Beautiful + Quiet Home with Amazing Amenities

Oakland, Maryland, United States

Bed 6

Bed

Bath 5

Bath

Sleep 16

Sleeps
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Exceptional(9)

$832.87

/ Nightly
Private Vacation Home

Dog Friendly Escape w/ Dock & Fire Pit

Oakland, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(10)

$832.92

/ Nightly
Private Vacation Home

Elevated Dog Friendly Escape w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

Bed 6

Bed

Bath 5

Bath

Sleep 16

Sleeps
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Exceptional(50)

$835.42

/ Nightly
Private Vacation Home

Luxury Log Chalet Overlooking Deep Creek

Oakland, Maryland, United States

Bed 5

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(6)

$839.09

/ Nightly
Private Vacation Home

Luxury Lake Escape w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

Bed 5

Bed

Bath 5

Bath

Sleep 12

Sleeps
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Exceptional(18)

$839.2

/ Nightly
Private Vacation Home

Sunset Pointe | Dock, Hot Tub, Pool Table!

Oakland, Maryland, United States

Bed 6

Bed

Bath 5

Bath

Sleep 16

Sleeps
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Exceptional(4)

$856.99

/ Nightly
Private Vacation Home

Dog Friendly, Lake Views, Dock & Cozy Nights

Oakland, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(1)

$857.16

/ Nightly
Private Vacation Home

As You Lake It | New Build, Hot Tub, Pool Table

Oakland, Maryland, United States

Bed 6

Bed

Bath 5

Bath

Sleep 12

Sleeps
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Exceptional(4)

$858.82

/ Nightly
Private Vacation Home

Lakefront Charm w/ Enchanted Kitchen & Deck

Oakland, Maryland, United States

Bed 5

Bed

Bath 6

Bath

Sleep 16

Sleeps
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Exceptional(8)

$861.21

/ Nightly
Private Vacation Home

Year-Round Gem w/Dock, Hot Tub & Pool Table

OAKLAND, Maryland, United States

Bed 6

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(1)

$874.47

/ Nightly
Private Vacation Home

New! Split Lakefront Home w/ Hot Tub & Dock

Oakland, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(35)

$880.14

/ Nightly
Private Vacation Home

Stargazer | Phenomenal Lakefront Views!

Oakland, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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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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Home Most popular vacation rentals in Oakland

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Exceptional(10)

$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(10)

$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(10)

$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(10)

$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(10)

$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(10)

$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(10)

$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(10)

$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(10)

$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(10)

$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