Skip to content

Vacation rentals in Oakland

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Oakland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Lil' Sumptin
SUPERHOST
Tiny house · 2 guests · 0 beds · 1 bath

Lil' SumptinLil' Sumptin is a totally unique Tiny House experience. A renovated travel trailer parked on a equally unique spot. We've added a bathroom, porch and deck. Fall asleep to the sounds of the nearby creek. Hang out at same creek the next day. Everything you need for a relaxing get away. We are right down the road from Herrington Manor and Swallow Falls State Parks. Deep Creek Lake is a short drive from here. Beautiful places to hike, bike and boat! We are close to town but you’d never know it!

SUGARBUSH - Sweet Serenity Tiny House
SUPERHOST
Entire cabin · 4 guests · 2 beds · 1 bath

SUGARBUSH - Sweet Serenity Tiny HouseWelcome to SUGARBUSH! "Suga" is a 450 sq. ft. custom built tiny house. She will comfortably accommodate 2 adults or a family with 2 small children. At this time we DO NOT allow pets. Suga sits on a 3+ acre lot that use to be used for cross country skiing. She got her name from two trails, Sugarbush Run and Sugarbush Shortcut that ran through the lot! We welcome you to stay and enjoy our wonderful little getaway here in Pleasant Valley. Adventure Awaits!!!

Lake’n It Easy Cabin
Entire cabin · 6 guests · 4 beds · 1 bath

Lake’n It Easy CabinCozy updated cabin with views of the lake from front porch! Full kitchen and bath. Queen bed in master,double bunk beds in second bedroom with a single trundle and washer and dryer. Walking distance to the lodge for dinner, indoor swimming, game room along with fitness center. Golf course view and mini golf! Short drive to boat house to rent a kayak and just around the bend enjoy a relaxing day at the beach.

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Oakland vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Oakland

  1. Entire rental unit
  2. Terra Alta
Lucky Duck * New LIsting*
SUPERHOST
  1. Entire residential home
  2. Terra Alta
Lake View Home w/Fire Pit, Indoor Pool, Dogs OK!
SUPERHOST
  1. Entire residential home
  2. Terra Alta
Dad's Dream, quiet lake home in the WV Mountains
SUPERHOST
  1. Entire residential home
  2. Oakland
Lazy Bear Cabin Oakland home in the woods.
  1. Entire cabin
  2. Terra Alta
The GetAway Cabin at Alpine lake resort 3-brm 2b
SUPERHOST
  1. Entire residential home
  2. Oakland
Valley of Hope Retreat
  1. Entire cabin
  2. Terra Alta
Wild Wild West - New Lake Listing
SUPERHOST
  1. Entire rental unit
  2. Loch Lynn Heights
Oasis in Oakland
SUPERHOST
  1. Entire cabin
  2. Oakland
May the forest be with you
SUPERHOST
  1. Entire chalet
  2. Oakland
Lake Forest Chalet- New Owners of 5 Star Home!
SUPERHOST
  1. Entire rental unit
  2. Oakland
Cozy studio nook, close to everything
  1. Entire residential home
  2. Oakland
Open-space 2 bedroom residential home with firepit

Nearby destinations