Vacation Home Rentals By Owner In Oakland, MD

Showing 20 Of 372 Vacation Rentals

$727.76

/ Nightly

Private Vacation Home

Charming Dog Friendly Lake Area Home w/ Hot Tub

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(6)

$742.56

/ Nightly

Private Vacation Home

Valhalla | Amazing Lakes Views, Hot Tub, Sauna, Game Room!

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$740.53

/ Nightly

Private Vacation Home

Chic Rustic Log Cabin Near Lake w/ Fire Pit

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(3)

$740.33

/ Nightly

Private Vacation Home

Prime Location w Hot tub & Firepit

Oakland, Maryland, United States

Bed

Bath

Sleeps

$739.27

/ Nightly

Private Vacation Home

Lakefront house, 2 bedroom 3 bath

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(3)

$738.23

/ Nightly

Private Vacation Home

Black Bear Lodge | Lake Access, Shared Indoor Pool

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(67)

$738.12

/ Nightly

Private Vacation Home

Lakefront 5BR retreat with hot tub, game room, and boat slip.

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(6)

$735.39

/ Nightly

Private Vacation Home

Stylish Lakefront Escape w/ Hot Tub, Bar & Dock

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$732.77

/ Nightly

Private Vacation Home

New! Woodsy Hideaway w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

Bed

Bath

Sleeps

$732.59

/ Nightly

Private Vacation Home

Evergreen: NEW, Lake Access, Hot Tub, Dogs OK, Fire Pit, Accessibility Features

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(16)

$732.02

/ Nightly

Private Vacation Home

Hot Tub Hideaway Near Deep Creek Fun

OAKLAND, Maryland, United States

Bed

Bath

Sleeps

Exceptional(7)

$729.91

/ Nightly

Private Vacation Home

Glencoe | Lakefront + Private Dock, 1 mi to Shops

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(1)

$706.48

/ Nightly

Private Vacation Home

Bear Foot Cove | Private Dock, 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(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(52)

$717.32

/ Nightly

Private Vacation Home

All About the View | Lakefront, Awe-Inspiring View

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(2)

$725.71

/ Nightly

Private Vacation Home

New! Wooded Lakefront Hideaway w/ Dock & Fire Pit

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(15)

$726.65

/ Nightly

Private Vacation Home

Putter Place | Gorgeous Lakefront, Water Views!

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(15)

$742.84

/ Nightly

Private vacation home

Dog Friendly Retreat Near Deep Creek w/ Hot Tub!

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(15)

$716.28

/ Nightly

Private vacation home

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(15)

$731.03

/ Nightly

Private vacation home

New! Woodsy Hideaway w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(15)

$731.28

/ Nightly

Private vacation home

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(15)

$738.12

/ Nightly

Private vacation home

Lakefront 5BR retreat with hot tub, game room, and boat slip.

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(15)

$739.25

/ Nightly

Private vacation home

Black Bear Lodge | Lake Access, Shared Indoor Pool

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(15)

$740.33

/ Nightly

Private vacation home

Prime Location w Hot tub & Firepit

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(15)

$763.19

/ Nightly

Cabin

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(15)

$762.78

/ Nightly

Private vacation home

Stylish Lakefront Escape w/ Hot Tub, Bar & Dock

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(15)

$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

$727.76

$742.56

$740.53

$740.33

$739.27

$738.23

$738.12

$735.39

$732.77

$732.59

$732.02

$729.91

$719.97

$706.48

$707.95

$708.06

$717.32

$719.68

$725.71

$726.65

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