Vacation Home Rentals By Owner In Oakland, MD

Showing 60 Of 372 Vacation Rentals

Exceptional(2)

$722.45

/ Nightly

Private Vacation Home

Hot Tub, Dock & Walkable Access to Deep Creek Fun

Oakland, Maryland, United States

Bed

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(7)

$719.68

/ Nightly

Private Vacation Home

Dog Friendly Retreat Near Deep Creek w/ Hot Tub!

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

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(7)

$707.95

/ Nightly

Private Vacation Home

Sleek Mountain Luxury Home w/ Dock Slip & Fire Pit

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(1)

$706.48

/ Nightly

Private Vacation Home

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$631.93

/ Nightly

Private Vacation Home

Gulfway Hideaway | Great Views, Hot Tub, Pool Table

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(12)

$650.4

/ Nightly

Private Vacation Home

Luxury Mountain Escape w/ Hot Tub & Fireplaces

OAKLAND, Maryland, United States

Bed

Bath

Sleeps

Exceptional(1)

$649.47

/ Nightly

Private Vacation Home

New! Gorgeous Mountain Cabin w/ Hot Tub & Games

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(168)

$648.74

/ Nightly

Private Vacation Home

American Pride | Dog Friendly, Dock Slip, Hot Tub

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(85)

$648.23

/ Nightly

Private Vacation Home

Fir Reel | Spacious Cabin, Hot Tub, Game Room

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(14)

$645.01

/ Nightly

Private Vacation Home

Peaceful Rustic Chalet w/ Hot Tub & Fireplace

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(8)

$639.31

/ Nightly

Private Vacation Home

5 Bedroom in Deep Creek

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(30)

$638.49

/ Nightly

Private Vacation Home

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(8)

$638.32

/ Nightly

Private Vacation Home

Stylish Lakeview Getaway w/ Hot Tub & Lake Access

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

Bed

Bath

Sleeps

Exceptional(92)

$635.51

/ Nightly

Private Vacation Home

Lazy Days | Charming Lakefront Cottage

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(1)

$634.5

/ Nightly

Private Vacation Home

Deep Creek Aframe Cabin

Garrett County, Maryland, United States

Bed

Bath

Sleeps

$616.33

/ Nightly

Private Vacation Home

New! Mountain Lake Area Getaway w/ 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

$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

Bed

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

Bed

Bath

Sleeps

$739.25

/ Nightly

Private vacation home

Black Bear Lodge | Lake Access, Shared Indoor Pool

Oakland, Maryland, United States

Bed

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

Bed

Bath

Sleeps

Vacation Home Rentals By Owner In Oakland, MD

$722.45

$719.97

$719.68

$717.32

$708.06

$707.95

$706.48

$631.93

$650.4

$649.47

$648.74

$648.23

$645.01

$639.31

$638.49

$638.32

$637.7

$635.51

$634.5

$616.33

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