Vacation Home Rentals By Owner In Oakland, MD

Showing 371 Of 371 Vacation Rentals

Exceptional(50)

$1600.95

/ Nightly

Private Vacation Home

Indoor Pool, Huge Home, Best View of the Lake!

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(9)

$1645.74

/ Nightly

Private Vacation Home

Grand Chestnut Lodge | Lakefront w/ Game Room, Hot Tub & Dock!

Oakland, Maryland, United States

Bed

Bath

Sleeps

$1666.11

/ Nightly

Private Vacation Home

5 bedroom, 4.5 bath Log Cabin in Deep Creek Lake

Oakland, 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

Exceptional(6)

$1736.47

/ Nightly

Private Vacation Home

The Haven | Lakefront + 8 Suites, Indoor Pool, Hot Tub, Dock!

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(23)

$1785.64

/ Nightly

Private Vacation Home

Luxury Log Chalet w/ Pool & Fireplace

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$1927.61

/ Nightly

Private Vacation Home

Private Lodge sleeps 31 guests Spectacular Views

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(1)

$2027.37

/ Nightly

Private Vacation Home

New! Luxury Lakefront w/ Pool, Dock & Hot Tub

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(8)

$2071.8

/ Nightly

Private Vacation Home

Under the Stars: Private Indoor & Outdoor Pools, 2 Hot Tubs, & BIG Lake

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(11)

$2659.28

/ Nightly

Private Vacation Home

20-Acre Estate w/ Pool, Games & Meeting Space

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(4)

$525.76

/ Nightly

Private Vacation Home

Spacious Family Gem ~ Scenic Lake Views ~ 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

Exceptional(4)

$742.84

/ Nightly

Private vacation home

Dog Friendly Retreat Near Deep Creek w/ Hot Tub!

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(4)

$716.28

/ Nightly

Private vacation home

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(4)

$731.03

/ Nightly

Private vacation home

New! Woodsy Hideaway w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(4)

$731.28

/ Nightly

Private vacation home

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(4)

$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(4)

$739.25

/ Nightly

Private vacation home

Black Bear Lodge | Lake Access, Shared Indoor Pool

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(4)

$740.33

/ Nightly

Private vacation home

Prime Location w Hot tub & Firepit

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(4)

$763.19

/ Nightly

Cabin

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(4)

$762.78

/ Nightly

Private vacation home

Stylish Lakefront Escape w/ Hot Tub, Bar & Dock

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(4)

$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

$1600.95

$1645.74

$1666.11

$1682.75

$1736.47

$1785.64

$1927.61

$2027.37

$2071.8

$2659.28

$525.76

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