Oakland Vacation Rentals

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Wisp'd Away
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Luxury lakefront home on Tranquil cove - 3.5 private acres w/ dock. Sledding hill, private trails, year-round fun. Fire pit, Hot Tub and much more

4 Bedrooms
3½ Bathrooms
4 Guides
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10 reviews
$688 / night (excl. fees & taxes)
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Mountain Air
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Cabin in the woods, low fees, hot tub, pool table, fire pit, swing set

4 Bedrooms
2½ Bathrooms
4 Guides
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71 reviews
$178 - $713 / night (excl. fees & taxes)
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Absolutely Shore
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Level lakefront, family-friendly, low fees, private dock

4 Bedrooms
3½ Bathrooms
4 Guides
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118 reviews
$270 - $815 / night (excl. fees & taxes)
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Black Eyed Susan
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Close to everything DCL, spacious cottage, fun for the whole family

3 Bedrooms
2½ Bathrooms
4 Guides
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68 reviews
$101 - $509 / night (excl. fees & taxes)
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New Lakefront~4/5 BR! Hot Tub~Game Rom & Firepit!
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New Lakefront~4/5 BR! Hot Tub~Game Rom & Firepit!

5 Bedrooms
3 Bathrooms
4 Guides
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2 reviews
$449 - $1933 / night (excl. fees & taxes)
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Mountain Escape! Deep Creek Lake, MD
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Cozy Mountain Escape with Hot Tub, Game Room, Fire Pit and More!

3 Bedrooms
2½ Bathrooms
4 Guides
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118 reviews
$160 - $868 / night (excl. fees & taxes)
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Mulligan Manor on WISP Mountain & Lodestone Golf!
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Deep Creek Lake / WISP area! HOT TUB, Game room with POOL Table, fire pit & amazing views! 🌄 1.5 miles from Lake and 3 mins from Wisp! HUGE Porch!

3 Bedrooms
2½ Bathrooms
4 Guides
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62 reviews
$230 - $799 / night (excl. fees & taxes)
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"Campfire Cottage" at Deep Creek Lake MD
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Cozy private cottage with hot tub, central air, huge fire pit, indoor fireplace and private dock slip!

3 Bedrooms
2 Bathrooms
4 Guides
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16 reviews
$299 / night (excl. fees & taxes)
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Indoor Pool Cabin! Brand New~Game Room~EV Charger
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Indoor Pool Cabin! Brand New~Game Room~EV Charger

5 Bedrooms
5 Bathrooms
4 Guides
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3 reviews
$699 - $1299 / night (excl. fees & taxes)
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Lakefront pup-friendly home on Deep Creek Lake!
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Lakefront pup-friendly home on Deep Creek Lake!

4 Bedrooms
3 Bathrooms
4 Guides
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29 reviews
$595 / night (excl. fees & taxes)
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The Blue Sky Bungalow: A-frame/Lake Access/Firepit
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The Blue Sky Bungalow: A-frame/Lake Access/Firepit

3 Bedrooms
2 Bathrooms
4 Guides
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44 reviews
$114 - $315 / night (excl. fees & taxes)
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Point View 2.0
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Brand New Lakefront Home with Unbeatable Lake Views Close to Everything!

4 Bedrooms
2 Bathrooms
4 Guides
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2 reviews
$450 / night (excl. fees & taxes)
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Bracken Lodge - 22 acres of private luxury & fun!
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Your private mountain retreat - 11 acres of forest, trails, views and fun! Minutes to everything Deep Creek but no noise or neighbors. Relax & unwind!

5 Bedrooms
5½ Bathrooms
4 Guides
$975 / night (excl. fees & taxes)
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Lake Front Home w/ Hot Tub & Firepit, walk to Wisp
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Lake View Retreat w/ Hot Tub, Walk to Wisp Resort!

3 Bedrooms
3 Bathrooms
4 Guides
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218 reviews
$237 - $800 / night (excl. fees & taxes)
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Slippery Slope Cabin! #1 in DCL!  Walk to Wisp!
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3 Bedroom / 3 Bath Cabin! Game Room~Pool Table, Skee-Ball & Arcade! HOT TUB, gas grill & walk to Wisp!! Close to everything in McHenry!

3 Bedrooms
3 Bathrooms
4 Guides
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113 reviews
$289 - $2853 / night (excl. fees & taxes)
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Deep Creek Serenity Retreat
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Deep Creek Serenity Retreat: Indoor Heated Pool, Patio, Hot Tub, Sauna, and Gym

6 Bedrooms
5½ Bathrooms
4 Guides
$850 / night (excl. fees & taxes)
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Hummingbird Retreat Ohiopyle
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Serene getaway near Ohiopyle, unique house and property on stream

3 Bedrooms
2 Bathrooms
4 Guides
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3 reviews
$225 / night (excl. fees & taxes)
    1 – 17 Rentals