Vacation Rentals in Oakland, Maryland

50 Properties Available

Private vacation home

New: Lakefront Luxury Home with Private Indoor Heated Pool!

$2046 / night

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Private vacation home

Under the Stars: Private Indoor & Outdoor Pools, 2 Hot Tubs, & BIG Lake

$1980 / night

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Private vacation home

VVS - Very Very Special: Private Dock in Prime Location, Hot Tub & Game Room

$1445 / night

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Private vacation home

New! Epic Lake Views, Games, Hot Tub Comfort & A/C

$1300 / night

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Private vacation home

LakeAccess 4BR DeckSlide OD Movies HotTub Kayaks

$1221 / night

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Private vacation home

Stylish Lakefront Home w/ Foosball & Hot Tub

$912 / night

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Private vacation home

New! Split Lakefront Home w/ Hot Tub & Dock

$896 / night

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Private vacation home

Lakefront Maryland Home - Deck, Grill & Pool Table

$883 / night

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Private vacation home

Angler's Cove: Lakefront, Private Dock, Hot Tub, Fire Pit!

$875 / night

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Private vacation home

Wynsome Run Lodge: Lakefront, Fireplaces, Dock Slip, Fire Pit!

$856 / night

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Private vacation home

Dog Friendly Escape w/ Dock & Fire Pit

$853 / night

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Private vacation home

Huge, Beautiful + Quiet Home with Amazing Amenities

$845 / night

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Private vacation home

5BR lakefront retreat with hot tub, sauna, & dock

$809 / night

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Chalet

Swings, Lakeview A-frame + Hot Tub, 120” screen

$781 / night

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Private vacation home

Lakeside Vista | Lakefront, Private Dock + Views

$775 / night

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Private vacation home

Cozy Chalet w/ Lake Access & Game Room

$751 / night

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Private vacation home

New Construction! Amazing Lakefront Home with Hot Tub + Firepit!

$751 / night

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Private vacation home

Lake Access Lodge w/ Fireplace & Hot Tub

$740 / night

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Private vacation home

Hot Tub, Dock & Walkable Access to Deep Creek Fun

$728 / night

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Private vacation home

Fab Lakeview + Lake Access + Dock Slip + Hot Tub!

$695 / night

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Agritourism

Beautiful 65 Acre Farm with Wrap Around Porch

$666 / night

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Private vacation home

Innisfree | Lake Front, Pet Friendly, Hot Tub, Dock

$660 / night

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Private vacation home

BEST outdoor amenities (2 dock slips, covered hot tub, sauna, pizza oven, more!)

$649 / night

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Private vacation home

Maple Ridge: New, Lake Access, Hot Tub, Sauna

$646 / night

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Private vacation home

Loch Nest | Lakefront, Private Dock, Dog Friendly!

$631 / night

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Private vacation home

Canoe Cottage | In the Heart of Deep Creek Lake!

$624 / night

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Private vacation home

Johnny Appleseed | Lakefront + Pool Access

$624 / night

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$New! Lakeside Paradise: Lakefront, Foosball Table, A\/C!$ Private vacation home

New! Lakeside Paradise: Lakefront, Foosball Table, A\/C!

$595 / night

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$Beautiful Lake View w\/Hot tub, Fireplace,& firepit$ Private vacation home

Beautiful Lake View w\/Hot tub, Fireplace,& firepit

$587 / night

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Private vacation home

Deep Creek Hideaway w/ Pool Table & Fire Pit

$586 / night

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Private vacation home

Pet Friendly! Huge + Central, Hot Tub

$586 / night

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Private vacation home

Peaceful Escape w/ Hot Tub, Fireplaces & Fire Pit

$575 / night

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$Lakefront\/Dock\/Amazing views HotTub$ Private vacation home

Lakefront\/Dock\/Amazing views HotTub

$566 / night

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Private vacation home

Best Location, lakefront, dockslip, family friendly, safe.

$558 / night

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Private vacation home

Sleek Chalet Retreat w/ Hot Tub & Fire Pit

$553 / night

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Chalet

Family Friendly Lakeside Chalet - Hot Tub, Game Room, Fireplace, & Near Wisp

$544 / night

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Cabin

The Lake House | 5BR/5BA Oakland Cabin | Hot Tub

$537 / night

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Private vacation home

Nature's Retreat | Private Dock, Community Pool!

$528 / night

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Private vacation home

Good Time Pine | 4BR/3.5BA Oakland Log Home w/ Hot Tub

$520 / night

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Private vacation home

Spacious Family Gem ~ Scenic Lake Views ~ Hot Tub!

$505 / night

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Private vacation home

Luxury 4BR Mansion - HOT TUB - Lake View - Oakland

$499 / night

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Private vacation home

Somewhere | Great Views, Boat Dock, Fire Pit

$495 / night

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Private vacation home

New! Skipper's Lagoon: Lakefront, Dogs Welcome, Dock Slip, Hot Tub!

$481 / night

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Private vacation home

S'more Fun | Pet Friendly, Ping Pong, Fire Pit, Boat Slip

$474 / night

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Private vacation home

Level lakefront, family-friendly, hot tub, low fees, private dock

$467 / night

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Private vacation home

Crosswinds | Hot Tub, Walk to Dining + Marina

$457 / night

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Private vacation home

Lakefront, Wooded, & Secluded Home - Family Dogs Welcome.

$455 / night

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Private vacation home

Biltmore Chalet | Hot Tub & Patio Dining + Pool Table!

$450 / night

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Private vacation home

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

$449 / night

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Private vacation home

New! Paradise Retreat: Lakefront, Dock Slip, Hot Tub, Pool Table!

$441 / night

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