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Oakland Vacation Rentals

1 - 42 of 42 rentals
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Tees 'N Skis - Oakland, MD Vacation Rental

Tees 'N Skis

Oakland, MD
4 Bed 3.5 Bath Sleeps 10
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Bear Necessity's - Oakland, MD Vacation Rental

Bear Necessity's

Oakland, MD
3 Bed 3 Bath Sleeps 10
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Laurel Cove - Oakland, MD Vacation Rental

Laurel Cove

Oakland, MD
6 Bed 6.5 Bath Sleeps 25
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Bee Tree II - Oakland, MD Vacation Rental

Bee Tree II

Oakland, MD
4 Bed 3 Bath Sleeps 10
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Cedar's Edge - Oakland, MD Vacation Rental

Cedar's Edge

Oakland, MD
3 Bed 1 Bath Sleeps 8
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Ashianeh - Oakland, MD Vacation Rental

Ashianeh

Oakland, MD
4 Bed 3 Bath Sleeps 10
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The Gathering - Oakland, MD Vacation Rental

The Gathering

Oakland, MD
5 Bed 4 Bath Sleeps 12
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Z Lake Retreat - Oakland, MD Vacation Rental

Z Lake Retreat

Oakland, MD
3 Bed 2.5 Bath Sleeps 8
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Great Escape - Oakland, MD Vacation Rental

Great Escape

Oakland, MD
2 Bed 2 Bath Sleeps 10
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Still Meadows - Oakland, MD Vacation Rental

Still Meadows

Oakland, MD
3 Bed 1 Bath Sleeps 6
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180 Degrees - Oakland, MD Vacation Rental

180 Degrees

Oakland, MD
3 Bed 4 Bath Sleeps 10
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Terp's Hideaway - Oakland, MD Vacation Rental

Terp's Hideaway

Oakland, MD
5 Bed 3 Bath Sleeps 11
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Eagle's Nest - Oakland, MD Vacation Rental

Eagle's Nest

Oakland, MD
3 Bed 2 Bath Sleeps 7
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Chalet in Hiding - Oakland, MD Vacation Rental

Chalet in Hiding

Oakland, MD
4 Bed 3 Bath Sleeps 12
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Mary's Landing - Oakland, MD Vacation Rental

Mary's Landing

Oakland, MD
3 Bed 2.5 Bath Sleeps 6
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5 Little Acorns - McHenry, MD Vacation Rental

5 Little Acorns

McHenry, MD
4 Bed 3.5 Bath Sleeps 10
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Ski Cove #2 - McHenry, MD Vacation Rental

Ski Cove #2

McHenry, MD
2 Bed 2.5 Bath Sleeps 6
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Waterfront Greens Chalet - Swanton, MD Vacation Rental

Waterfront Greens Chalet

Swanton, MD
4 Bed 3.5 Bath Sleeps 10
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Harmony Retreat - Swanton, MD Vacation Rental

Harmony Retreat

Swanton, MD
2 Bed 2 Bath Sleeps 6
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Casa Miranda - Swanton, MD Vacation Rental

Casa Miranda

Swanton, MD
5 Bed 4 Bath Sleeps 14
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Ohana Retreat - McHenry, MD Vacation Rental

Ohana Retreat

McHenry, MD
3 Bed 2.5 Bath Sleeps 8
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Life's A Bear - McHenry, MD Vacation Rental

Life's A Bear

McHenry, MD
2 Bed 2 Bath Sleeps 8
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A Wispful Dream - McHenry, MD Vacation Rental

A Wispful Dream

McHenry, MD
4 Bed 3 Bath Sleeps 10
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3 Hartwood Village - McHenry, MD Vacation Rental

3 Hartwood Village

McHenry, MD
3 Bed 2 Bath Sleeps 9
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Birds' Nest - Swanton, MD Vacation Rental

Birds' Nest

Swanton, MD
2 Bed 1.5 Bath Sleeps 4
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VOW Slopeside #29 - McHenry, MD Vacation Rental

VOW Slopeside #29

McHenry, MD
3 Bed 3 Bath Sleeps 10
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Lazy Bear Lodge - Swanton, MD Vacation Rental

Lazy Bear Lodge

Swanton, MD
3 Bed 2 Bath Sleeps 10
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Sunflower - Swanton, MD Vacation Rental

Sunflower

Swanton, MD
3 Bed 2 Bath Sleeps 10
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Driftwood #6 - McHenry, MD Vacation Rental

Driftwood #6

McHenry, MD
2 Bed 1 Bath Sleeps 5
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VOW Winding Way 11 - McHenry, MD Vacation Rental

VOW Winding Way 11

McHenry, MD
2 Bed 3 Bath Sleeps 8
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Kara's Chalet - McHenry, MD Vacation Rental

Kara's Chalet

McHenry, MD
2 Bed 1 Bath Sleeps 6
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Two Much Fun - Swanton, MD Vacation Rental

Two Much Fun

Swanton, MD
5 Bed 4.5 Bath Sleeps 14
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Haley's Lakeside Cottage - McHenry, MD Vacation Rental

Haley's Lakeside Cottage

McHenry, MD
3 Bed 2 Bath Sleeps 6
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October Moon - Swanton, MD Vacation Rental

October Moon

Swanton, MD
3 Bed 3 Bath Sleeps 8
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Mainstead - McHenry, MD Vacation Rental

Mainstead

McHenry, MD
3 Bed 2 Bath Sleeps 8
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Laurel Lodge - Swanton, MD Vacation Rental

Laurel Lodge

Swanton, MD
4 Bed 2.5 Bath Sleeps 12
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Ski Harbor #15 - McHenry, MD Vacation Rental

Ski Harbor #15

McHenry, MD
3 Bed 2.5 Bath Sleeps 8
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Ski Harbor #19 - McHenry, MD Vacation Rental

Ski Harbor #19

McHenry, MD
4 Bed 2.5 Bath Sleeps 10
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Water's Edge - McHenry, MD Vacation Rental

Water's Edge

McHenry, MD
3 Bed 2 Bath Sleeps 10
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Pinederosa - McHenry, MD Vacation Rental

Pinederosa

McHenry, MD
4 Bed 2 Bath Sleeps 8
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