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Oakland Vacation Rentals

1 - 33 of 33 rentals
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The Gathering - Oakland, MD Vacation Rental

The Gathering

Oakland, MD
5 Bed 4 Bath Sleeps 12
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Ashianeh - Oakland, MD Vacation Rental

Ashianeh

Oakland, MD
4 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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Still Meadows - Oakland, MD Vacation Rental

Still Meadows

Oakland, MD
3 Bed 1 Bath Sleeps 6
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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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Mary's Landing - Oakland, MD Vacation Rental

Mary's Landing

Oakland, MD
3 Bed 2.5 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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Bee Tree II - Oakland, MD Vacation Rental

Bee Tree II

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

Terp's Hideaway

Oakland, MD
5 Bed 3 Bath Sleeps 11
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Great Escape - Oakland, MD Vacation Rental

Great Escape

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

A Wispful Dream

McHenry, MD
4 Bed 3 Bath Sleeps 10
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Casa Miranda - Swanton, MD Vacation Rental

Casa Miranda

Swanton, MD
5 Bed 4 Bath Sleeps 14
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Sunset View - Swanton, MD Vacation Rental

Sunset View

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

Sunflower

Swanton, MD
3 Bed 2 Bath Sleeps 10
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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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Pee Wee Acres - Swanton, MD Vacation Rental

Pee Wee Acres

Swanton, MD
3 Bed 1.5 Bath Sleeps 8 (6 Adults Max)
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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 Cove #2 - McHenry, MD Vacation Rental

Ski Cove #2

McHenry, MD
2 Bed 2.5 Bath Sleeps 6
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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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Mainstead - McHenry, MD Vacation Rental

Mainstead

McHenry, MD
3 Bed 2 Bath Sleeps 8
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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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Driftwood #6 - McHenry, MD Vacation Rental

Driftwood #6

McHenry, MD
2 Bed 1 Bath Sleeps 5
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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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Kara's Chalet - McHenry, MD Vacation Rental

Kara's Chalet

McHenry, MD
2 Bed 1 Bath Sleeps 6
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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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VOW Slopeside #29 - McHenry, MD Vacation Rental

VOW Slopeside #29

McHenry, MD
3 Bed 3 Bath Sleeps 10
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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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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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October Moon - Swanton, MD Vacation Rental

October Moon

Swanton, MD
3 Bed 3 Bath Sleeps 8
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About Oakland

Oakland rated 4.8 out of 5 based on 33 reviews Oakland, MD

Oakland's visitors know that time slows down during a walk past the main street's historic sights and shops, and the magic lingers through a drive out to nearby Deep Creek Lake, where outdoor adventure resides year-round. Book one of our vacation rentals in Oakland to experience Maryland's forests and mountains in every season, and stick around for the town's quaint charms. 

Oakland, MD: A Main Street Community

Whether you're out shopping for antiques or ordering an old-fashioned milkshake at Englander's, your stay at one of our Oakland vacation rentals means a peek into a simpler time. Join locals at the Oakland Golf Club for a round on a championship course, or make your way down the Glades or 88 Bridge walking and biking paths for some scenic exercise. A day's drive brings you to Baltimore or Pittsburgh, while neighboring towns such as McHenry and Swanton are just a short drive away.

Year-Round Outdoor Adventure in Oakland, MD

Oakland sits in the heart of Garrett County's woods, and guests at our Oakland rentals encounter Deep Creek adventure in any season. A 14-mile drive brings you to Wisp's winter ski slopes, while summer means rafting tours and kayaking on the Youghiogheny River right outside of town. 

Deep Creek Lake, a destination for bass fishermen, beckons adventure seekers with boating, water skiing, and more, while Deep Creek Lake State Park is home to some of the area's most satisfying hiking and camping.

When the lake freezes over, try your hand at ice fishing. Never gone dog sledding? You'll get your chance at Husky Power in the nearby town of Accident, where sled dogs pull passengers over snow and dry ground alike. 

No matter the season, our vacation rentals in Oakland are your key to the beauty of the Deep Creek area!

Photo Credit: marabuchi via Flickr

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