Home Vacation Home Rentals By Owner In Oakland, MD

Showing 360 Of 372 Vacation Rentals
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$1222.71

/ Nightly
Private Vacation Home

Luxor Mountaintop Cabin-Castle at Deep Creek Lake

Oakland, Maryland, United States

Bed 7

Bed

Bath 5

Bath

Sleep 22

Sleeps
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Exceptional(11)

$1225.11

/ Nightly
Private Vacation Home

Dog Friendly Luxury Escape w/ Hot Tub & Views

OAKLAND, Maryland, United States

Bed 7

Bed

Bath 6

Bath

Sleep 20

Sleeps
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Exceptional(27)

$1229.23

/ Nightly
Private Vacation Home

Friday's Escape | 5 Master Suites! Stunning Lakefront + Hot Tub

Oakland, Maryland, United States

Bed 7

Bed

Bath 6

Bath

Sleep 18

Sleeps
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Exceptional(5)

$1246.1

/ Nightly
Private Vacation Home

The Birch Bower: Luxury Lakefront Home

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 10

Sleeps
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Exceptional(8)

$1250.49

/ Nightly
Private Vacation Home

Hot Tub, Fire Pit & Stunning Lake Views

Oakland, Maryland, United States

Bed 8

Bed

Bath 7

Bath

Sleep 24

Sleeps
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Exceptional(90)

$1253.57

/ Nightly
Private Vacation Home

Deep Creek Ski Boat Golf Fish prvt indoor pool hot tub updated cancellation plcy

McHenry, Maryland, United States

Bed 8

Bed

Bath 7

Bath

Sleep 20

Sleeps
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$1267.68

/ Nightly
Private Vacation Home

Copper Canoe | Indoor Pool, Hot Tub, Movie Theater

Oakland, Maryland, United States

Bed 6

Bed

Bath 5

Bath

Sleep 16

Sleeps
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$1272.96

/ Nightly
Private Vacation Home

Dog Friendly Ranch Escape w/ Ponds & Trails

Oakland, Maryland, United States

Bed 5

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(8)

$1285.76

/ Nightly
Private Vacation Home

Chic Lake Stay w/ Pool, Dock & Fireplaces

Oakland, Maryland, United States

Bed 5

Bed

Bath 6

Bath

Sleep 14

Sleeps
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Exceptional(83)

$1288.25

/ Nightly
Private Vacation Home

Celebration at Deep Creek | Indoor Pool, Game Room, Hot Tub

Oakland, Maryland, United States

Bed 8

Bed

Bath 7

Bath

Sleep 22

Sleeps
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Exceptional(7)

$1300.42

/ Nightly
Private Vacation Home

New! Epic Lake Views, Games, Hot Tub Comfort & A/C

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(2)

$1303.09

/ Nightly
Private Vacation Home

Serene Lakefront Getaway w/ Dock, Hot Tub & Views

Oakland, Maryland, United States

Bed 4

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(8)

$1305.6

/ Nightly
Private Vacation Home

Dog Friendly Mountain Escape w/ Pool & Game Room

Oakland, Maryland, United States

Bed 5

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(22)

$1375.44

/ Nightly
Private Vacation Home

Ever After | Lakefront, Hot Tub + Dock Slip

Oakland, Maryland, United States

Bed 7

Bed

Bath 8

Bath

Sleep 18

Sleeps
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Exceptional(1)

$1408.61

/ Nightly
Private Vacation Home

Modern Deep Creek Lakefront Home, Movie Theater, Hot Tub, 7BR/6BA, Sleeps 16

Oakland, Maryland, United States

Bed 7

Bed

Bath 6

Bath

Sleep 16

Sleeps
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Exceptional(8)

$1442.94

/ Nightly
Private Vacation Home

Lakefront Chalet w/ Pool, Private Dock, & Hot Tub

OAKLAND, Maryland, United States

Bed 8

Bed

Bath 6

Bath

Sleep 24

Sleeps
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Exceptional(13)

$1455.51

/ Nightly
Private Vacation Home

2 Homes, 1 Estate w/ Dock, Fire Pit & Game Room

Oakland, Maryland, United States

Bed 10

Bed

Bath 6

Bath

Sleep 18

Sleeps
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Exceptional(9)

$1502.28

/ Nightly
Private Vacation Home

Dog Friendly Luxury Estate w/ Hot Tub & Dock

Oakland, Maryland, United States

Bed 9

Bed

Bath 5

Bath

Sleep 25

Sleeps
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Exceptional(8)

$1509.56

/ Nightly
Private Vacation Home

Magical Lake Escape w/ Dock Slip & Game Room

Oakland, Maryland, United States

Bed 8

Bed

Bath 7

Bath

Sleep 22

Sleeps
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Exceptional(6)

$1520.8

/ Nightly
Private Vacation Home

VVS - Very Very Special: Private Dock in Prime Location, Hot Tub & Game Room

Oakland, Maryland, United States

Bed 8

Bed

Bath 7

Bath

Sleep 19

Sleeps
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Home Most popular vacation rentals in Oakland

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Exceptional(6)

$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(6)

$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(6)

$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(6)

$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(6)

$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(6)

$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(6)

$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(6)

$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(6)

$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