Vacation Home Rentals By Owner In Oakland, MD

Showing 220 Of 372 Vacation Rentals

Exceptional(3)

$637.7

/ Nightly

Private Vacation Home

Knotty Dog Lodge- Hot Tub, Fire Pit, Pet Friendly!

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(8)

$638.32

/ Nightly

Private Vacation Home

Stylish Lakeview Getaway w/ Hot Tub & Lake Access

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(30)

$638.49

/ Nightly

Private Vacation Home

Innisfree | Lake Front, Pet Friendly, Hot Tub, Dock

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(8)

$639.31

/ Nightly

Private Vacation Home

5 Bedroom in Deep Creek

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(14)

$645.01

/ Nightly

Private Vacation Home

Peaceful Rustic Chalet w/ Hot Tub & Fireplace

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(85)

$648.23

/ Nightly

Private Vacation Home

Fir Reel | Spacious Cabin, Hot Tub, Game Room

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(168)

$648.74

/ Nightly

Private Vacation Home

American Pride | Dog Friendly, Dock Slip, Hot Tub

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(1)

$649.47

/ Nightly

Private Vacation Home

New! Gorgeous Mountain Cabin w/ Hot Tub & Games

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(12)

$650.4

/ Nightly

Private Vacation Home

Luxury Mountain Escape w/ Hot Tub & Fireplaces

OAKLAND, Maryland, United States

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Bath

Sleeps

Exceptional(73)

$652.38

/ Nightly

Private Vacation Home

Lakefront/Dock/Amazing views HotTub

Oakland, Maryland, United States

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Bath

Sleeps

$654.02

/ Nightly

Private Vacation Home

Just GOREgeous A Charming Lake House Escape LAKE ACCESS

Oakland, Maryland, United States

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Bath

Sleeps

$654.55

/ Nightly

Private Vacation Home

BEST outdoor amenities (2 dock slips, covered hot tub, sauna, pizza oven, more!)

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(7)

$655.16

/ Nightly

Private Vacation Home

Stylish Lake Retreat w/ Hot Tub, Dock & Fire Pit

Oakland, Maryland, United States

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Bath

Sleeps

$656.7

/ Nightly

Private Vacation Home

Secluded Wooded Hideaway w/ Hot Tub & Pool Table

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(131)

$657.11

/ Nightly

Private Vacation Home

Peaceful Lakefront! Private deep water dock, evening sun, quiet dead end street!

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(15)

$662.32

/ Nightly

Private Vacation Home

Dog Friendly Log Cabin Near Deep Creek Lake

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(12)

$666.11

/ Nightly

Private Vacation Home

Dog Friendly Chalet w/ Dock, Hot Tub & Fire Pit

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(15)

$669.18

/ Nightly

Private Vacation Home

Rockwell | 4BR En Suites | Dog Friendly + Hot Tub & Pool

Oakland, Maryland, United States

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Bath

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Exceptional(6)

$675.42

/ Nightly

Private Vacation Home

Luxury Townhome w/ Hot Tub Near Lake & Wisp

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(113)

$682.43

/ Nightly

Private Vacation Home

Boxer Overlook | Lake Views, Hot Tub, Pet Friendly, Mountainside

Oakland, Maryland, United States

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Bath

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Rent a place that suits your needs

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Bed

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Sleeps

Vacation Home Rentals By Owner In Oakland, MD

$637.7

$638.32

$638.49

$639.31

$645.01

$648.23

$648.74

$649.47

$650.4

$652.38

$654.02

$654.55

$655.16

$656.7

$657.11

$662.32

$666.11

$669.18

$675.42

$682.43

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