Home Vacation Home Rentals By Owner In Oakland, MD

Showing 20 Of 371 Vacation Rentals
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$724.58

/ 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)

$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)

$741.64

/ 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(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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$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)

$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(12)

$738.84

/ Nightly
Private Vacation Home

Deep Creek Gem w/ Dock, Fire Pit, Views & Hot Tub

Oakland, Maryland, United States

Bed 7

Bed

Bath 3

Bath

Sleep 14

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(29)

$736.99

/ 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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Exceptional(39)

$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(2)

$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(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(2)

$713.98

/ Nightly
Private Vacation Home

Hot Tub, Dock & Walkable Access to Deep Creek Fun

Oakland, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 11

Sleeps
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Exceptional(3)

$696.67

/ Nightly
Private Vacation Home

Owl Be Back | Pet Friendly, Hot Tub, Lake Access!

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 10

Sleeps
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Exceptional(51)

$697

/ Nightly
Private Vacation Home

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Oakland, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(1)

$705.59

/ Nightly
Private Vacation Home

Bear Foot Cove | Private Dock, Hot Tub, Fire Pit

Oakland, Maryland, United States

Bed 5

Bed

Bath 6

Bath

Sleep 12

Sleeps
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Exceptional(3)

$706.85

/ Nightly
Private Vacation Home

New! Lake Area Mountain Gem w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(52)

$711.28

/ Nightly
Private Vacation Home

All About the View | Lakefront, Awe-Inspiring View

Oakland, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 10

Sleeps
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Exceptional(7)

$719.08

/ Nightly
Private Vacation Home

Sleek Mountain Luxury Home w/ Dock Slip & Fire Pit

Oakland, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 13

Sleeps
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Exceptional(16)

$722.81

/ 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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Home Most popular vacation rentals in Oakland

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Exceptional(16)

$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(16)

$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(16)

$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(16)

$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(16)

$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(16)

$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(16)

$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(16)

$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(16)

$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(16)

$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