Vacation Rentals By Owner In Oakland, MD

Showing 569 Of 569 Vacation Rentals

Exceptional(2)

$731.03

/ Nightly

Private Vacation Home

New! Woodsy Hideaway w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(3)

$444.14

/ Nightly

Private Vacation Home

Keep Dreaming | Hot Tub, Fire Pit, Great Location

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(2)

$628.86

/ Nightly

Private Vacation Home

4BR lake-access retreat with hot tub, pool table, dogs OK, and sleeps 11

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(6)

$837.87

/ Nightly

Private Vacation Home

Luxury Lake Escape w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(45)

$414.98

/ Nightly

Chalet

Spacious family-friendly chalet w/fenced dog run & large deck near the lake/Wisp

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(4)

$910.92

/ Nightly

Private Vacation Home

Johnny Appleseed | Lakefront, Hot Tub, Private Dock

Oakland, Maryland, United States

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Bath

Sleeps

Exceptional(22)

$465.3

/ Nightly

Private Vacation Home

Cedars on the Rocks | Mins to Activities + Skiing

Oakland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(216)

$587.43

/ Nightly

Private Vacation Home

Sunny Escape 2 - A new era for a well loved lake front home

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

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Bath

Sleeps

Rent a place that suits your needs

Cabin

View 49 Cabin

Private vacation home

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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

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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

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Bath

Sleeps

Vacation Rentals By Owner In Oakland, MD

$731.03

$444.14

$628.86

$837.87

$414.98

$910.92

$465.3

$587.43

$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