Vacation Home Rentals By Owner In Oakland, MD

Showing 120 Of 372 Vacation Rentals

Exceptional(17)

$1092.62

/ Nightly

Private Vacation Home

Champagne Taste | Level, Lakefront, Private Dock

Oakland, Maryland, United States

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Sleeps

Exceptional(36)

$1116.4

/ Nightly

Private Vacation Home

St. Bart's Retreat | Pet Friendly, Lakefront Home!

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(3)

$1137.56

/ Nightly

Private Vacation Home

Spacious 5-bedroom house 4 miles from Wisp. Close to all things in Deep Creek!

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(15)

$1152.48

/ Nightly

Private Vacation Home

Deep Creek Gem w/ Views, Fire Pit & Pool Table

OAKLAND, Maryland, United States

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Bath

Sleeps

Exceptional(17)

$1166.94

/ Nightly

Private Vacation Home

La Bella Vita | Amazing Lake Views, Upscale Decor

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(5)

$1200.38

/ Nightly

Private Vacation Home

Cozy Dog Friendly, Private Dock & Fire Pit

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(10)

$1201.08

/ Nightly

Private Vacation Home

Dog Friendly Deep Creek Retreat w/ Hot Tub

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(17)

$1207.98

/ Nightly

Private Vacation Home

Tranquil Lakefront w/ Twin Hot Tubs & Dock

Oakland, Maryland, United States

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Bath

Sleeps

$1222.71

/ Nightly

Private Vacation Home

Luxor Mountaintop Cabin-Castle at Deep Creek Lake

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(11)

$1225.11

/ Nightly

Private Vacation Home

Dog Friendly Luxury Escape w/ Hot Tub & Views

OAKLAND, Maryland, United States

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Bath

Sleeps

Exceptional(27)

$1229.23

/ Nightly

Private Vacation Home

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

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(5)

$1246.1

/ Nightly

Private Vacation Home

The Birch Bower: Luxury Lakefront Home

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(8)

$1250.49

/ Nightly

Private Vacation Home

Hot Tub, Fire Pit & Stunning Lake Views

Oakland, Maryland, United States

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Bath

Sleeps

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

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Bath

Sleeps

$1267.68

/ Nightly

Private Vacation Home

Copper Canoe | Indoor Pool, Hot Tub, Movie Theater

Oakland, Maryland, United States

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Bath

Sleeps

$1272.96

/ Nightly

Private Vacation Home

Dog Friendly Ranch Escape w/ Ponds & Trails

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(8)

$1285.76

/ Nightly

Private Vacation Home

Chic Lake Stay w/ Pool, Dock & Fireplaces

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

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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

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Rent a place that suits your needs

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Vacation Home Rentals By Owner In Oakland, MD

$1092.62

$1116.4

$1137.56

$1152.48

$1166.94

$1200.38

$1201.08

$1207.98

$1222.71

$1225.11

$1229.23

$1246.1

$1250.49

$1253.57

$1267.68

$1272.96

$1285.76

$1652.16

$1682.75

$1657.42

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