Home Vacation Home Rentals By Owner In Oakland, MD

Showing 260 Of 372 Vacation Rentals
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Exceptional(8)

$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)

$725.71

/ Nightly
Private Vacation Home

New! Wooded Lakefront Hideaway w/ Dock & Fire Pit

Oakland, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 11

Sleeps
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Exceptional(3)

$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(15)

$726.65

/ Nightly
Private Vacation Home

Putter Place | Gorgeous Lakefront, Water Views!

Oakland, Maryland, United States

Bed 6

Bed

Bath 5

Bath

Sleep 16

Sleeps
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$727.76

/ Nightly
Private Vacation Home

Charming Dog Friendly Lake Area Home w/ Hot Tub

Oakland, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(7)

$729.91

/ Nightly
Private Vacation Home

Glencoe | Lakefront + Private Dock, 1 mi to Shops

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(16)

$732.02

/ Nightly
Private Vacation Home

Hot Tub Hideaway Near Deep Creek Fun

OAKLAND, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 14

Sleeps
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$732.59

/ Nightly
Private Vacation Home

Evergreen: NEW, Lake Access, Hot Tub, Dogs OK, Fire Pit, Accessibility Features

Oakland, Maryland, United States

Bed 4

Bed

Bath 5

Bath

Sleep 11

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(6)

$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(67)

$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)

$738.23

/ 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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$739.27

/ Nightly
Private Vacation Home

Lakefront house, 2 bedroom 3 bath

Oakland, Maryland, United States

Bed 2

Bed

Bath 3

Bath

Sleep 4

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(2)

$740.53

/ Nightly
Private Vacation Home

Chic Rustic Log Cabin Near Lake w/ Fire Pit

Oakland, Maryland, United States

Bed 4

Bed

Bath 5

Bath

Sleep 12

Sleeps
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Exceptional(6)

$742.56

/ Nightly
Private Vacation Home

Valhalla | Amazing Lakes Views, Hot Tub, Sauna, Game Room!

Oakland, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(3)

$743.23

/ Nightly
Private Vacation Home

Nature Escape w/ Dock, Fire Pit & Foosball

Oakland, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 14

Sleeps
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Exceptional(5)

$743.52

/ Nightly
Private Vacation Home

Woodsy Retreat w/ Fire Pit, Hot Tub & Game Room

Oakland, Maryland, United States

Bed 5

Bed

Bath 6

Bath

Sleep 14

Sleeps
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Exceptional(5)

$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
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Exceptional(29)

$747.02

/ Nightly
Private Vacation Home

Heavenly Grove | Fire Pit & Pool Table! Walk to Lake!

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Home Most popular vacation rentals in Oakland

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Exceptional(29)

$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(29)

$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(29)

$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(29)

$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(29)

$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(29)

$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
Slider Thumb
Exceptional(29)

$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(29)

$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(29)

$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(29)

$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