Vacation Home Rentals By Owner In Oakland, MD

Showing 80 Of 372 Vacation Rentals

Exceptional(92)

$635.51

/ Nightly

Private Vacation Home

Lazy Days | Charming Lakefront Cottage

Oakland, Maryland, United States

Bed

Bath

Sleeps

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(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(11)

$686.36

/ Nightly

Private Vacation Home

Skylodge | Log Home, Hot Tub, Fun Attractions!

Oakland, Maryland, United States

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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

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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

Bed

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(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(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

Bed

Bath

Sleeps

Exceptional(2)

$685.14

/ Nightly

Private Vacation Home

Stylish Lakeview Cabin w/ Pool Table & Hot Tub

Oakland, Maryland, United States

Bed

Bath

Sleeps

Rent a place that suits your needs

Cabin

View 49 Cabin

Private vacation home

View 371 Private vacation home

Condo

View 57 Condo

Most popular vacation rentals in Oakland

Exceptional(2)

$742.84

/ Nightly

Private vacation home

Dog Friendly Retreat Near Deep Creek w/ Hot Tub!

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$716.28

/ Nightly

Private vacation home

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

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(2)

$731.03

/ Nightly

Private vacation home

New! Woodsy Hideaway w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(2)

$731.28

/ 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(2)

$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(2)

$739.25

/ Nightly

Private vacation home

Black Bear Lodge | Lake Access, Shared Indoor Pool

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(2)

$740.33

/ Nightly

Private vacation home

Prime Location w Hot tub & Firepit

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$763.19

/ Nightly

Cabin

Secluded Mtn Cabin: 7BR, Pool, Hot Tub, Game Room

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$762.78

/ Nightly

Private vacation home

Stylish Lakefront Escape w/ Hot Tub, Bar & Dock

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$758.95

/ Nightly

Private vacation home

Luxury Expansive Lakefront, Newly Renovated!

Oakland, Maryland, United States

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Bath

Sleeps

Vacation Home Rentals By Owner In Oakland, MD

$635.51

$637.7

$638.32

$638.49

$639.31

$645.01

$648.23

$648.74

$649.47

$650.4

$692.71

$686.36

$687.96

$688.92

$689.09

$691.05

$697

$704.27

$697.48

$685.14

Rent a place that suits your needs

Most popular vacation rentals in Oakland

$742.84

$716.28

$731.03

$731.28

$738.12

$739.25

$740.33

$763.19

$762.78

$758.95

Most Popular Cities in Maryland