Vacation Home Rentals By Owner In Oakland, MD

Showing 100 Of 372 Vacation Rentals

Exceptional(13)

$768.78

/ Nightly

Private Vacation Home

Waterfront Fun Dog Friendly Home w/ Hot Tub & Dock

OAKLAND, Maryland, United States

Bed

Bath

Sleeps

$769.41

/ Nightly

Private Vacation Home

Lakefront 4BR/3.5BA retreat with beautiful views

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(93)

$769.84

/ Nightly

Private Vacation Home

Fancy Free | Lakefront, Hot Tub, Pet Friendly

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(7)

$770.81

/ Nightly

Private Vacation Home

Modern + Stunning! Private + Flat Lakefront!

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(79)

$774.53

/ Nightly

Private Vacation Home

Dog Friendly Mountain Chalet w/ Fireplaces

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(8)

$775.65

/ Nightly

Private Vacation Home

Lakeside Vista | Lakefront, Private Dock + Views

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(64)

$777.24

/ Nightly

Private Vacation Home

Highland Retreat | Incredible Lakefront, Deck

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(4)

$778.58

/ Nightly

Private Vacation Home

Dog Friendly Lake Home w/ Easy Walk to Dock & Pool

Oakland, Maryland, United States

Bed

Bath

Sleeps

$781.53

/ Nightly

Private Vacation Home

Cozy Lakefront Escape w/ Private Dock & Hot Tub

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(3)

$783.05

/ Nightly

Private Vacation Home

Nautical Lakefront Retreat w/ Dock & Hot Tub

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(35)

$784.15

/ Nightly

Private Vacation Home

Eagle's Landing | Lakefront Home on Quiet Cove

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(2)

$788.7

/ Nightly

Private Vacation Home

Secluded Lake Escape w/ Dock, Fire Pit & Views

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(6)

$792.41

/ Nightly

Private Vacation Home

Dockside Bliss w/ Hot Tub, Fire Pit & Big Deck

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(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

Bed

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

Bed

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

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

$742.84

/ Nightly

Private vacation home

Dog Friendly Retreat Near Deep Creek w/ Hot Tub!

Oakland, Maryland, United States

Bed

Bath

Sleeps

$716.28

/ Nightly

Private vacation home

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

$731.03

/ Nightly

Private vacation home

New! Woodsy Hideaway w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

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Bath

Sleeps

$731.28

/ Nightly

Private vacation home

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

$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

$739.25

/ Nightly

Private vacation home

Black Bear Lodge | Lake Access, Shared Indoor Pool

Oakland, Maryland, United States

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Bath

Sleeps

$740.33

/ Nightly

Private vacation home

Prime Location w Hot tub & Firepit

Oakland, Maryland, United States

Bed

Bath

Sleeps

$763.19

/ Nightly

Cabin

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

$762.78

/ Nightly

Private vacation home

Stylish Lakefront Escape w/ Hot Tub, Bar & Dock

Oakland, Maryland, United States

Bed

Bath

Sleeps

$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

$768.78

$769.41

$769.84

$770.81

$774.53

$775.65

$777.24

$778.58

$781.53

$783.05

$784.15

$788.7

$792.41

$1246.1

$1201.08

$1207.98

$1222.71

$1225.11

$1229.23

$1267.68

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