Oakland Cabin Rentals

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Cabin Rentals in Oakland

New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

Oakland MD

$637 nightly

$720 total

Dec 11 - Dec 12

Total with taxes and fees

With a stay at this cabin in Oakland, you'll be within a 15-minute drive of Deep Creek Lake and Wisp Resort.

Hot Tub

Kitchen

That Special Place

Oakland MD

$452 nightly

$479 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

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

Cabin in the Woods

Oakland MD

Located in Oakland, this cabin is a 4-minute drive from Youghiogheny Wild River Natural Environmental Area and 5 minutes from Youghiogheny River.

Hot Tub

Kitchen

Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!

Oakland MD

Located in Oakland, this cabin is within a 15-minute drive of Deep Creek Lake and Wisp Resort.

Swallow Falls Cabin 1- Cozy 1-Bedroom Perfect for a Romantic Getaway!

Oakland MD

With a stay at this cabin in Oakland, you'll be within a 15-minute drive of Deep Creek Lake and Wisp Resort.

Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek

Oakland MD

When you stay at this cabin in Oakland, you'll be on a lake, a 2-minute drive from Deep Creek Lake and 9 minutes from Wisp Resort.

Dog-friendly secluded cabin with hot tub, firepit, lawn games, & great deck

Oakland MD

When you stay at this cabin in Oakland, you'll be within a 10-minute drive of Cranesville Swamp Natural Area and Cranesville Swamp Preserve.

Hot Tub

Kitchen

Rustic Luxury w/ Pool Table, Dock & Views

Oakland MD

With a stay at this cabin in Oakland, you'll be on the waterfront, within a 15-minute drive of Deep Creek Lake and Mount Nebo Wildlife Management Area.

3BR Cabin, Hot Tub, Lake Access, Pet-Friendly – 30% Weekly Discount Excl. Summer

Oakland MD

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

The winter is coming !!!

Oakland MD

$384 nightly

$407 total

Dec 15 - Dec 16

Total with taxes and fees

With a stay at this cabin in Oakland, you'll be within a 15-minute drive of Deep Creek Lake and Wisp Resort.

Recreational Therapy- Private 2 Bedroom with Hot Tub and Firepit

Oakland MD

With a stay at this cabin in Oakland, you'll be in the mountains, within a 15-minute drive of Deep Creek Lake and Swallow Falls State Park.

Luxury Private Ski Cabin on 6 acres-6BR, Hot Tub, Massage Chair, Deep Creek Lake

Oakland MD

Located in Oakland, this cabin is a 1-minute drive from Youghiogheny River and 8 minutes from Cathedral State Park.

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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.