Vacation Home Rentals By Owner In Oakland, MD

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

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(1)

$756.69

Wooded Tranquil Retreat w/ Hot Tub & Fireplace

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(8)

$758.95

Luxury Expansive Lakefront, Newly Renovated!

Oakland, Maryland, United States

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Bath

Sleeps

$760.91

Charming Dog Friendly Cottage w/ Modern Touches

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(6)

$764.51

Cozy Chalet w/ Lake Access & Game Room

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(6)

$767.41

Chic Dog Friendly Retreat w/ Hot Tub & Fireplace

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(13)

$768.78

Waterfront Fun Dog Friendly Home w/ Hot Tub & Dock

OAKLAND, Maryland, United States

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Bath

Sleeps

$769.41

Lakefront 4BR/3.5BA retreat with beautiful views

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(93)

$769.84

Fancy Free | Lakefront, Hot Tub, Pet Friendly

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(7)

$770.81

Modern + Stunning! Private + Flat Lakefront!

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(79)

$774.53

Dog Friendly Mountain Chalet w/ Fireplaces

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(8)

$775.65

Lakeside Vista | Lakefront, Private Dock + Views

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(64)

$777.24

Highland Retreat | Incredible Lakefront, Deck

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(4)

$778.58

Dog Friendly Lake Home w/ Easy Walk to Dock & Pool

Oakland, Maryland, United States

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Bath

Sleeps

$781.53

Cozy Lakefront Escape w/ Private Dock & Hot Tub

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(3)

$783.05

Nautical Lakefront Retreat w/ Dock & Hot Tub

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(35)

$784.15

Eagle's Landing | Lakefront Home on Quiet Cove

Oakland, Maryland, United States

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Bath

Sleeps

$788.7

Secluded Lake Escape w/ Dock, Fire Pit & Views

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(6)

$792.41

Dockside Bliss w/ Hot Tub, Fire Pit & Big Deck

Oakland, Maryland, United States

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Bath

Sleeps

$794.4

View 372 Private vacation home

Secluded Chalet w/ Hot Tub & Pool Table

Oakland, Maryland, United States

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Bath

Sleeps

Rent a place that suits your needs

Private vacation home

Cabin

View 49 Cabin

Condo

View 57 Condo

Most popular vacation rentals in Oakland

$738.12

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

$719.68

Dog Friendly Retreat Near Deep Creek w/ Hot Tub!

Oakland, Maryland, United States

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Bath

Sleeps

$719.97

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

Oakland, Maryland, United States

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Bath

Sleeps

$724.63

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

Oakland, Maryland, United States

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Bath

Sleeps

$725.89

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

Oakland, Maryland, United States

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Bath

Sleeps

$732.77

New! Woodsy Hideaway w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

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Bath

Sleeps

$735.39

Stylish Lakefront Escape w/ Hot Tub, Bar & Dock

Oakland, Maryland, United States

Bed

Bath

Sleeps

$756.84

Cabin

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

$756.69

Wooded Tranquil Retreat w/ Hot Tub & Fireplace

Oakland, Maryland, United States

Bed

Bath

Sleeps

$746.39