Vacation Rentals By Owner In Oakland, MD

Showing 540 Of 570 Vacation Rentals

Exceptional(93)

$769.84

/ Nightly

Private Vacation Home

Fancy Free | Lakefront, Hot Tub, Pet Friendly

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(86)

$395.54

/ Nightly

Private Vacation Home

Cedarwoods | Hot Tub + Private Wooded Setting

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

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Exceptional(60)

$515.07

/ Nightly

Private Vacation Home

Cedar Ridge | Private Hot Tub, Fantastic Location

Oakland, Maryland, United States

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Exceptional(29)

$403.91

/ Nightly

Private Vacation Home

Knotty Pines | Dock Slip + Near State Parks

Oakland, Maryland, United States

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Sleeps

Exceptional(15)

$341.53

/ Nightly

Private Vacation Home

By the Stream | Tranquil + Streamside, Near Wisp!

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(25)

$395.04

/ Nightly

Private Vacation Home

Acorn Cottage | Luxe Vibes, Outdoor Living Spaces + Breathtaking Lake Views!

Oakland, Maryland, United States

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Sleeps

Exceptional(2)

$942.34

/ Nightly

Private Vacation Home

Treeline Lodge | Walk to Honi + Lakefront + Tiki Bar Vibes

Oakland, Maryland, United States

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Sleeps

Exceptional(39)

$719.97

/ 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(3)

$725.89

/ Nightly

Private Vacation Home

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

Oakland, Maryland, United States

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Sleeps

Exceptional(3)

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Private Vacation Home

Spacious Lake Escape w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(1)

$1088.33

/ Nightly

Private Vacation Home

Lakefront Oasis w/ Hot Tub, Pool, Courts & 2 Homes

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(13)

$1455.51

/ Nightly

Private Vacation Home

2 Homes, 1 Estate w/ Dock, Fire Pit & Game Room

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(4)

$763.19

/ Nightly

Cabin

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

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(2)

$602.43

/ Nightly

Private Vacation Home

New! Dog Friendly Retreat w/ Hot Tub & Fireplace

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(7)

$485.78

/ Nightly

Private Vacation Home

Deep Creek Escape w/ Hot Tub & Fireplaces

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(20)

$308.75

/ Nightly

Private Vacation Home

Windy Acres | Dog Friendly + Hot Tub & Great Views!

Oakland, Maryland, United States

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Sleeps

Exceptional(7)

$770.81

/ Nightly

Private Vacation Home

Modern + Stunning! Private + Flat Lakefront!

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(4)

$568.62

/ Nightly

Chalet

ON THE ROCKS Lakeside Mountain Chalet

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(10)

$832.92

/ Nightly

Private Vacation Home

Elevated Dog Friendly Escape w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

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Bath

Sleeps

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Cabin

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Private vacation home

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Condo

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Most popular vacation rentals in Oakland

Exceptional(10)

$742.84

/ Nightly

Private vacation home

Dog Friendly Retreat Near Deep Creek w/ Hot Tub!

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(10)

$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(10)

$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(10)

$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(10)

$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(10)

$739.25

/ Nightly

Private vacation home

Black Bear Lodge | Lake Access, Shared Indoor Pool

Oakland, Maryland, United States

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Bath

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Exceptional(10)

$740.33

/ Nightly

Private vacation home

Prime Location w Hot tub & Firepit

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(10)

$763.19

/ Nightly

Cabin

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(10)

$762.78

/ Nightly

Private vacation home

Stylish Lakefront Escape w/ Hot Tub, Bar & Dock

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(10)

$758.95

/ Nightly

Private vacation home

Luxury Expansive Lakefront, Newly Renovated!

Oakland, Maryland, United States

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Vacation Rentals By Owner In Oakland, MD

$769.84

$395.54

$1229.23

$515.07

$403.91

$341.53

$395.04

$942.34

$719.97

$725.89

$1088.33

$1455.51

$763.19

$602.43

$485.78

$308.75

$770.81

$568.62

$832.92

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