Vacation Home Rentals By Owner In Oakland, MD

Showing 40 Of 372 Vacation Rentals

$739.27

/ Nightly

Private Vacation Home

Lakefront house, 2 bedroom 3 bath

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

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(6)

$742.56

/ Nightly

Private Vacation Home

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

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(6)

$792.41

/ Nightly

Private Vacation Home

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$788.7

/ Nightly

Private Vacation Home

Secluded Lake Escape w/ Dock, Fire Pit & Views

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(35)

$784.15

/ Nightly

Private Vacation Home

Eagle's Landing | Lakefront Home on Quiet Cove

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(3)

$783.05

/ Nightly

Private Vacation Home

Nautical Lakefront Retreat w/ Dock & Hot Tub

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

Bed

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

Exceptional(64)

$777.24

/ Nightly

Private Vacation Home

Highland Retreat | Incredible Lakefront, Deck

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(8)

$775.65

/ Nightly

Private Vacation Home

Lakeside Vista | Lakefront, Private Dock + Views

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

Bed

Bath

Sleeps

Exceptional(7)

$770.81

/ Nightly

Private Vacation Home

Modern + Stunning! Private + Flat Lakefront!

Oakland, Maryland, United States

Bed

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(29)

$747.02

/ Nightly

Private Vacation Home

Heavenly Grove | Fire Pit & Pool Table! Walk to Lake!

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(1)

$756.69

/ Nightly

Private Vacation Home

Wooded Tranquil Retreat w/ Hot Tub & Fireplace

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(12)

$749.28

/ Nightly

Private Vacation Home

Deep Creek Gem w/ Dock, Fire Pit, Views & Hot Tub

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(8)

$758.95

/ Nightly

Private Vacation Home

Luxury Expansive Lakefront, Newly Renovated!

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(8)

$742.84

/ Nightly

Private vacation home

Dog Friendly Retreat Near Deep Creek w/ Hot Tub!

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(8)

$716.28

/ Nightly

Private vacation home

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(8)

$731.03

/ Nightly

Private vacation home

New! Woodsy Hideaway w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(8)

$731.28

/ Nightly

Private vacation home

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(8)

$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(8)

$739.25

/ Nightly

Private vacation home

Black Bear Lodge | Lake Access, Shared Indoor Pool

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(8)

$740.33

/ Nightly

Private vacation home

Prime Location w Hot tub & Firepit

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(8)

$763.19

/ Nightly

Cabin

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

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(8)

$762.78

/ Nightly

Private vacation home

Stylish Lakefront Escape w/ Hot Tub, Bar & Dock

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(8)

$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

$739.27

$740.33

$740.53

$742.56

$769.41

$792.41

$788.7

$784.15

$783.05

$781.53

$778.58

$777.24

$775.65

$774.53

$770.81

$769.84

$747.02

$756.69

$749.28

$758.95

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