Oakland Vacation Rentals

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Vacation Rentals in Oakland

Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing

Oakland MD

When you stay at this vacation home in Oakland, you'll be on the waterfront, within a 15-minute drive of Deep Creek Lake and Wisp Resort.

Hot Tub

Kitchen

Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip

Oakland MD

With a stay at this vacation home in Oakland, you'll be on the waterfront, within a 10-minute drive of Deep Creek Lake and Youghiogheny Wild River Natural Environmental Area.

Hot Tub

Kitchen

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Oakland MD

With a stay at this vacation home in Oakland, you'll be on the waterfront, within a 10-minute drive of Deep Creek Lake and Youghiogheny Wild River Natural Environmental Area.

Hot Tub

Kitchen

Beautiful lakefront home with hot tub, game room, washer/dryer & private dock

Oakland MD

With a stay at this vacation home in Oakland (Blakeslee), you'll be a 3-minute drive from Deep Creek Lake and 14 minutes from Mount Nebo Wildlife Management Area.

Pool

Hot Tub

Central Deep Creek Retreat w/ Hot Tub

Oakland MD

When you stay at this vacation home in Oakland, you'll be on a lake, within a 15-minute drive of Deep Creek Lake and Wisp Resort.

Hot Tub

Kitchen

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

Oakland MD

With a stay at this vacation home in Oakland (Paradise Point), you'll be within a 15-minute drive of Deep Creek Lake and Wisp Resort.

Hot Tub

Kitchen

Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi

Oakland MD

When you stay at this vacation home in Oakland, you'll be in the mountains, a 3-minute drive from Deep Creek Lake and 10 minutes from Wisp Resort.

Kitchen

Washer

Private Lodge sleeps 25 guests Spectacular Views

Oakland MD

$1,370 nightly

$1,452 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

With a stay at this vacation home in Oakland, you'll be within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State Park.

Kitchen

Washer

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

Oakland MD

When you stay at this vacation home in Oakland, you'll be on the waterfront, a 1-minute drive from Deep Creek Lake and 8 minutes from Wisp Resort.

Hot Tub

Kitchen

Lakeslee Lodge: Spacious 6BR retreat with lake access and community pool in Oakland, MD.

Oakland MD

With a stay at this vacation home in Oakland (Blakeslee), you'll be a 3-minute drive from Deep Creek Lake and 13 minutes from Mount Nebo Wildlife Management Area.

Pool

Hot Tub

Vibrant Lakeview Chalet w/ Huge Deck

OAKLAND MD

With a stay at this vacation home in Oakland (The View), you'll be within a 15-minute drive of Deep Creek Lake and Wisp Resort.

Hot Tub

Kitchen

Serene Mountain Escape: Hot Tub, Foosball, Views

Oakland MD

With a stay at this vacation home in Oakland, you'll be in the mountains, within a 10-minute drive of Deep Creek Lake and Mount Nebo Wildlife Management Area.

Hot Tub

Kitchen

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.