Vacation Rentals By Owner In Oakland, MD

Showing 560 Of 569 Vacation Rentals

Exceptional(4)

$337.95

/ Nightly

Private Vacation Home

An Apple Away | Verdant Views + Hot Tub

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(1)

$624.96

/ Nightly

Private Vacation Home

Deep Creek Aframe Cabin

Garrett County, Maryland, United States

Bed

Bath

Sleeps

Exceptional(9)

$647.66

/ Nightly

Cabin

Group Getaway w/ Loft, Fireplace & Hot Tub

McHenry, Maryland, United States

Bed

Bath

Sleeps

Exceptional(90)

$1682.75

/ Nightly

Private Vacation Home

AMAZING LAKE FRONT 7 BR Home, Hot Tub, Fire Pit, Dock, Pool Table, NEW FIRE PIT

Oakland, Maryland, United States

Bed

Bath

Sleeps

$536.65

/ Nightly

Private Vacation Home

Charming Luxe Cabin w/ Hot Tub, Fire Pit & Views

Oakland, Maryland, United States

Bed

Bath

Sleeps

$1272.02

/ Nightly

Private Vacation Home

Dog Friendly Ranch Escape w/ Ponds & Trails

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(8)

$294.15

/ Nightly

Private Vacation Home

3-bed, charming modernized cottage tucked into wooded hillside in Deep Creek, MD

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(24)

$366.1

/ Nightly

Private Vacation Home

Evergreen | Wooded Views from Balcony + Private Hot Tub

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(1)

$512.97

/ Nightly

Private Vacation Home

New! Dog Friendly Wooded Escape w/ Hot Tub

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(3)

$366.23

/ Nightly

Condo

Will O' The Wisp: 508G Two Bedroom/One Bath

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(117)

$201.22

/ Nightly

Private Vacation Home

Sisters Treehouse

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(415)

$346.49

/ Nightly

Cabin

Spa Cabin: Lakefront w Private Sauna & Hot Tub, Kayaks, Dock, 5 Star Clean Rated

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(38)

$272.45

/ Nightly

Private Vacation Home

Mountain Escape | Hot Tub | Game Room | Fire Pit

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$600.31

/ Nightly

Private Vacation Home

Lake Access Lodge w/ Fireplace & Hot Tub

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$550.6

/ Nightly

Private Vacation Home

Dog Friendly Chalet Near Deep Creek w/ Dock Slip

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

Bed

Bath

Sleeps

Exceptional(10)

$606.67

/ Nightly

Private Vacation Home

Family-Friendly Lodge Minutes from the Lake

Oakland, Maryland, United States

Bed

Bath

Sleeps

$780.31

/ Nightly

Private Vacation Home

Cozy Lakefront Escape w/ Private Dock & Hot Tub

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(22)

$366.4

/ Nightly

Private Vacation Home

Private Family Home w/ Deck, Porch + Forest Views!

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(3)

$323.58

/ Nightly

Condo

Will O' The Wisp: 107B One Bedroom/One Bath

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

Bed

Bath

Sleeps

Vacation Rentals By Owner In Oakland, MD

$337.95

$624.96

$647.66

$1682.75

$536.65

$1272.02

$294.15

$366.1

$512.97

$366.23

$201.22

$346.49

$272.45

$600.31

$550.6

$769.41

$606.67

$780.31

$366.4

$323.58

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