Vacation Home Rentals By Owner In Oakland, MD

Showing 140 Of 372 Vacation Rentals

Exceptional(1)

$2033.42

/ Nightly

Private Vacation Home

New! Luxury Lakefront w/ Pool, Dock & Hot Tub

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(2)

$1946.69

/ Nightly

Private Vacation Home

Private Lodge sleeps 31 guests Spectacular Views

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(6)

$1779.78

/ Nightly

Private Vacation Home

The Haven | Lakefront + 8 Suites, Indoor Pool, Hot Tub, Dock!

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(23)

$1770.8

/ Nightly

Private Vacation Home

Luxury Log Chalet w/ Pool & Fireplace

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(91)

$1682.75

/ Nightly

Private Vacation Home

AMAZING LAKE FRONT 7 BR Home, Hot Tub, Fire Pit, Dock, Pool Table, NEW FIRE PIT

Oakland, Maryland, United States

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Bath

Sleeps

$1657.42

/ Nightly

Private Vacation Home

5 bedroom, 4.5 bath Log Cabin in Deep Creek Lake

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(9)

$1652.16

/ Nightly

Private Vacation Home

Grand Chestnut Lodge | Lakefront w/ Game Room, Hot Tub & Dock!

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(50)

$1587.87

/ Nightly

Private Vacation Home

Indoor Pool, Huge Home, Best View of the Lake!

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(3)

$1553.04

/ Nightly

Private Vacation Home

Cozy Lake Retreat w/ Dock, Fire Pit & Views

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(8)

$1442.94

/ Nightly

Private Vacation Home

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

OAKLAND, Maryland, United States

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Bath

Sleeps

Exceptional(7)

$1300.42

/ Nightly

Private Vacation Home

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

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(2)

$1303.09

/ Nightly

Private Vacation Home

Serene Lakefront Getaway w/ Dock, Hot Tub & Views

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(8)

$1305.6

/ Nightly

Private Vacation Home

Dog Friendly Mountain Escape w/ Pool & Game Room

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(22)

$1375.44

/ Nightly

Private Vacation Home

Ever After | Lakefront, Hot Tub + Dock Slip

Oakland, Maryland, United States

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Bath

Sleeps

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

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Bath

Sleeps

Exceptional(9)

$1502.28

/ Nightly

Private Vacation Home

Dog Friendly Luxury Estate w/ Hot Tub & Dock

Oakland, Maryland, United States

Bed

Bath

Sleeps

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

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Bath

Sleeps

Exceptional(8)

$1509.56

/ Nightly

Private Vacation Home

Magical Lake Escape w/ Dock Slip & Game Room

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(64)

$1032.88

/ Nightly

Private Vacation Home

Amazing Central Location! Lakefront! Hot tub/dock!

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(13)

$1455.51

/ Nightly

Private Vacation Home

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

Oakland, Maryland, United States

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Bath

Sleeps

Rent a place that suits your needs

Private vacation home

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Cabin

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Condo

View 57 Condo

Most popular vacation rentals in Oakland

Exceptional(13)

$738.12

/ Nightly

Private vacation home

Lakefront 5BR retreat with hot tub, game room, and boat slip.

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(13)

$719.68

/ Nightly

Private vacation home

Dog Friendly Retreat Near Deep Creek w/ Hot Tub!

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(13)

$719.97

/ Nightly

Private vacation home

Central Lake House, Private Dock! Walk to Area Hot Spots!

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(13)

$724.63

/ Nightly

Private vacation home

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

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(13)

$725.89

/ Nightly

Private vacation home

New! Historic Lake Cottage w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(13)

$732.77

/ Nightly

Private vacation home

New! Woodsy Hideaway w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(13)

$735.39

/ Nightly

Private vacation home

Stylish Lakefront Escape w/ Hot Tub, Bar & Dock

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(13)

$756.84

/ Nightly

Cabin

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

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(13)

$756.69

/ Nightly

Private vacation home

Wooded Tranquil Retreat w/ Hot Tub & Fireplace

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(13)

$746.39

/ Nightly

Private vacation home

Relaxing Lakefront in Prime Location w/Lake Access

Oakland, Maryland, United States

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Bath

Sleeps

Vacation Home Rentals By Owner In Oakland, MD

$2033.42

$1946.69

$1779.78

$1770.8

$1682.75

$1657.42

$1652.16

$1587.87

$1553.04

$1442.94

$1300.42

$1303.09

$1305.6

$1375.44

$1408.61

$1502.28

$1520.8

$1509.56

$1032.88

$1455.51

Rent a place that suits your needs

Most popular vacation rentals in Oakland

$738.12

$719.68

$719.97

$724.63

$725.89

$732.77

$735.39

$756.84

$756.69

$746.39

Most Popular Cities in Maryland