Vacation Home Rentals By Owner In Oakland, MD

Showing 240 Of 372 Vacation Rentals

Exceptional(2)

$685.14

/ Nightly

Private Vacation Home

Stylish Lakeview Cabin w/ Pool Table & Hot Tub

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(11)

$686.36

/ Nightly

Private Vacation Home

Skylodge | Log Home, Hot Tub, Fun Attractions!

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$687.96

/ Nightly

Private Vacation Home

Lake View Lodge with Hot Tub, Sauna, Fire Pit, Games, Gym, & EV Friendly

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(9)

$688.92

/ Nightly

Private Vacation Home

Maple Ridge: New, Lake Access, Hot Tub, Sauna

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(3)

$689.09

/ Nightly

Private Vacation Home

Leap Away | Private Dock, Hot Tub, & Pool Table!

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(22)

$691.05

/ Nightly

Private Vacation Home

Solar Delight | Lafe View, Private Dock, Hot Tub!

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(10)

$692.71

/ Nightly

Private Vacation Home

Mountain Laurel: Accessibility Features, Lake Access, Dog Friendly

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(14)

$695.24

/ Nightly

Private Vacation Home

Fab Lakeview + Lake Access + Dock Slip + Hot Tub!

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(3)

$696.67

/ Nightly

Private Vacation Home

Owl Be Back | Pet Friendly, Hot Tub, Lake Access!

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(51)

$697

/ Nightly

Private Vacation Home

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(2)

$697.48

/ Nightly

Private Vacation Home

4BR lake-access retreat with hot tub, pool table, dogs OK, and sleeps 11

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(14)

$704.27

/ Nightly

Private Vacation Home

Spacious 5BR Retreat w/ Ping Pong & Fire Pit

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(9)

$704.9

/ Nightly

Private Vacation Home

Mountain Escape w/ Fire Pit, Pool Table & Hot Tub!

OAKLAND, Maryland, United States

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Bath

Sleeps

Exceptional(1)

$706.48

/ Nightly

Private Vacation Home

Bear Foot Cove | Private Dock, Hot Tub, Fire Pit

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(7)

$707.95

/ Nightly

Private Vacation Home

Sleek Mountain Luxury Home w/ Dock Slip & Fire Pit

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(3)

$708.06

/ Nightly

Private Vacation Home

New! Lake Area Mountain Gem w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(52)

$717.32

/ Nightly

Private Vacation Home

All About the View | Lakefront, Awe-Inspiring View

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(7)

$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(39)

$719.97

/ Nightly

Private Vacation Home

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$722.45

/ Nightly

Private Vacation Home

Hot Tub, Dock & Walkable Access to Deep Creek Fun

Oakland, Maryland, United States

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Bath

Sleeps

Rent a place that suits your needs

Private vacation home

View 372 Private vacation home

Cabin

View 49 Cabin

Condo

View 57 Condo

Most popular vacation rentals in Oakland

Exceptional(2)

$738.12

/ Nightly

Private vacation home

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$719.68

/ Nightly

Private vacation home

Dog Friendly Retreat Near Deep Creek w/ Hot Tub!

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$719.97

/ Nightly

Private vacation home

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$724.63

/ Nightly

Private vacation home

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$725.89

/ Nightly

Private vacation home

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$732.77

/ Nightly

Private vacation home

New! Woodsy Hideaway w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$735.39

/ Nightly

Private vacation home

Stylish Lakefront Escape w/ Hot Tub, Bar & Dock

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$756.84

/ Nightly

Cabin

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$756.69

/ Nightly

Private vacation home

Wooded Tranquil Retreat w/ Hot Tub & Fireplace

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(2)

$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

$685.14

$686.36

$687.96

$688.92

$689.09

$691.05

$692.71

$695.24

$696.67

$697

$697.48

$704.27

$704.9

$706.48

$707.95

$708.06

$717.32

$719.68

$719.97

$722.45

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