Oakland Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Oakland

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Oakland MD

With a stay at this vacation home in Oakland, you'll be a 3-minute drive from Deep Creek Lake and 7 minutes from Wisp Resort.

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.

Lakefront/Dock/Amazing views HotTub

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 Funland Go Cart Racetrace.

Sisters Treehouse

Oakland MD

When you stay at this vacation home in Oakland, you'll be on a lake, a 3-minute drive from Deep Creek Lake and 7 minutes from Wisp Resort.

Kitchen

Washer

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.

Amazing Central Location! Lakefront! Hot tub/dock!

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.

West Oak: New home, 3 suites, hot tub, boat slip, outdoor fireplace

Oakland MD

With a stay at this vacation home in Oakland, you'll be on a lake, within a 5-minute drive of Deep Creek Lake and Youghiogheny Wild River Natural Environmental Area.

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

Oakland MD

With a stay at this vacation home in Oakland, you'll be a 3-minute drive from Deep Creek Lake and 9 minutes from Wisp Resort.

Dog-friendly house on the lake, central AC, & EV charger

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 Funland Go Cart Racetrace.

AMAZING LAKE FRONT 7 BR Home, Dog Friendly, Hot Tub, Fire Pit, Dock, Pool Table

Oakland MD

With a stay at this vacation home, you'll be centrally located in Oakland, a 1-minute drive from Deep Creek Lake and 12 minutes from Wisp Resort.

Elegant Home Away: Hot Tub, Game Room, Kid Friendly!

Oakland MD

Located in Oakland, this vacation home is on a lake, within a 5-minute walk of Youghiogheny River and Youghiogheny Wild River Natural Environmental Area.

Deep Creek Gem w/ Dock, Fire Pit, Views & Hot Tub

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 Funland Go Cart Racetrace.

Don't see what you're looking for?

See all available properties in Oakland

View all properties

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.