Home Vacation Rentals By Owner In Oakland, MD

Showing 20 Of 569 Vacation Rentals
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Exceptional(131)

$657.11

/ Nightly
Private Vacation Home

Peaceful Lakefront! Private deep water dock, evening sun, quiet dead end street!

Oakland, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(9)

$1069.64

/ Nightly
Private Vacation Home

Vibrant Lakeview Chalet w/ Huge Deck

OAKLAND, Maryland, United States

Bed 6

Bed

Bath 5

Bath

Sleep 15

Sleeps
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$392.73

/ Nightly
Cabin

Cozy Deep Creek Log Cabin - Hot Tub, Firepit & Dock Slip

Oakland, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 12

Sleeps
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Exceptional(140)

$570.28

/ Nightly
Private Vacation Home

5 STAR OWNER Managed, Lake Xcess, dock, Pool, Pickle-ball, Home Theater, firepit

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 12

Sleeps
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$610.19

/ Nightly
Private Vacation Home

New! Mountain Lake Area Getaway w/ Hot Tub!

Oakland, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(3)

$426.15

/ Nightly
Private Vacation Home

Great Escape | 2BR/2BA Lakefront Dock & Firepit

Oakland, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(193)

$555.98

/ Nightly
Private Vacation Home

Lake Front 4 Bedroom Home With A Dock Centrally Located 5 Minutes To Wisp & Unos

Oakland, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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$903.17

/ Nightly
Cabin

Majestic Mountain Cabin Retreat near Deep Creek Lake in Maryland

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(18)

$497.84

/ Nightly
Cabin

Cozy Log Cabin w/ Hot Tub & Fireplace

Oakland, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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$236.31

/ Nightly
Cabin

Contemporary 2BR Cabin - HOT TUB & Fireplace - Oakland

Oakland, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$269.05

/ Nightly
Lodge

Bright and Cheery Suite for a Weekend Getaway near Savage River State Forest, Maryland

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$248.1

/ Nightly
Lodge

Romantic Suite Rental with a Hot Tub near Savage River State Forest, Maryland

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(2)

$636

/ Nightly
Cabin

Authentic Cabin in the Woods!

Oakland, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 12

Sleeps
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$265.2

/ Nightly
Lodge

Luxury Rental for a Romantic Getaway near Swallow Falls State Park, Maryland

Oakland, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(27)

$266.32

/ Nightly
Condo

Lake Loft at Deep Creek Lake

Oakland, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 5

Sleeps
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$607.66

/ Nightly
Private Vacation Home

Blue Skies | 5BR/4BA Oakland retreat w/ hot tub

Oakland, Maryland, United States

Bed 6

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(3)

$1075.63

/ Nightly
Private Vacation Home

Spacious 5-bedroom house 4 miles from Wisp. Close to all things in Deep Creek!

Oakland, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 13

Sleeps
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$739.27

/ Nightly
Private Vacation Home

Lakefront house, 2 bedroom 3 bath

Oakland, Maryland, United States

Bed 2

Bed

Bath 3

Bath

Sleep 4

Sleeps
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Exceptional(15)

$589.51

/ Nightly
Private Vacation Home

Rockwell | 4BR En Suites | Dog Friendly + Hot Tub & Pool

Oakland, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 10

Sleeps
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$525.9

/ Nightly
Private Vacation Home

Everwoods @ Deep Creek Lake - Speakeasy, hot tub, bunk room on private acreage

Oakland, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Home Most popular vacation rentals in Oakland

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$742.84

/ Nightly
Private vacation home

Dog Friendly Retreat Near Deep Creek w/ Hot Tub!

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 11

Sleeps
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$716.28

/ Nightly
Private vacation home

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

Oakland, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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$731.03

/ Nightly
Private vacation home

New! Woodsy Hideaway w/ Hot Tub & Fire Pit

Oakland, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 12

Sleeps
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$731.28

/ Nightly
Private vacation home

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

Oakland, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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$738.12

/ Nightly
Private vacation home

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

Oakland, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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$739.25

/ Nightly
Private vacation home

Black Bear Lodge | Lake Access, Shared Indoor Pool

Oakland, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 12

Sleeps
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$740.33

/ Nightly
Private vacation home

Prime Location w Hot tub & Firepit

Oakland, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 12

Sleeps
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$763.19

/ Nightly
Cabin

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

Oakland, Maryland, United States

Bed 7

Bed

Bath 4

Bath

Sleep 18

Sleeps
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$762.78

/ Nightly
Private vacation home

Stylish Lakefront Escape w/ Hot Tub, Bar & Dock

Oakland, Maryland, United States

Bed 4

Bed

Bath 5

Bath

Sleep 12

Sleeps
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$758.95

/ Nightly
Private vacation home

Luxury Expansive Lakefront, Newly Renovated!

Oakland, Maryland, United States

Bed 4

Bed

Bath 6

Bath

Sleep 10

Sleeps

Most Popular Cities in Maryland