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Vacation rentals in Oakland

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.

Casa Cossick
SUPERHOSTEntire townhouse · 6 guests · 2 beds · 1 bath
Casa Cossick

Seconds away from the lake, Trader's Coffee House, Brenda's Pizzeria, High Mountain Sports, and minutes away from Wisp Ski Resort, entertainment, shopping, food, and anything else you could want.

What guests are saying:

“Photos don’t do this place justice! My favorite part of Zach’s spot was his patio, great views of the lake and sunset. WiFi worked out perfectly to work from home. Such a great location and cozy spot, only a 10 min drive to Deep Creek Lake State Park. Walkable distance to Brenda’s Pizzeria (highly recommend the shrimp scampi pizza) and Ace’s down the road has great crab cake sandwiches. Highly recommend and would stay again!”

Winter is Coming
SUPERHOSTEntire cabin · 10 guests · 3 beds · 3 baths
Winter is Coming

Your mountain vacation will be filled with magical memories when you choose to stay in this spectacular 3 master suite bedroom log home. You and your guests will immediately feel at home when you step through the front door. Luxurious décor compliments the gorgeous hardwood floors giving the cabin a warm and inviting feel. Cuddle up in front of the wood fireplace after an invigorating day of snowboarding at nearby Wisp Resort or enjoy your morning coffee on the covered porch swing.

What guests are saying:

“Chris was a wonderful host. We loved our stay. “Winter Is Coming” was a great place to unwind from any stresses and still be close to everything. We came for a long weekend and enjoyed every moment. We went to Swallow Falls, rented a boat, explored Oakland a bit and relaxed in the hot tub. Time went too fast. Wish we had stayed longer.”

Priv. Indoor Pool, Hot Tub, Free Golf&Mini,Tennis
Entire house · 14 guests · 11 beds · 5 baths
Priv. Indoor Pool, Hot Tub, Free Golf&Mini,Tennis

Clubhouse Chalet Private Indoor Pool Wisp Ski Resort 7 miles away BUSH FAMILY VACATIONED HERE IN 2009 - ASK FOR COMMUNITY NEWSLETTER Tennis courts, Mini golf, 3 par golf right next to the house (ALL FREE) Canoe and kayak racks by lake access (5 minute walk) Catch and Release fishing pond (10 minute walk) Covered Deck w/ grill (hooked to gas line) and furniture overlooking the tennis courts and Mini Golf Patio w/ Hot Tub, Fire Pit and furniture overlooking the golf course and lake Pool table

What guests are saying:

“I highly recommend this beautiful cozy and spacious home as it had everything a family would want from A to Z as a vacation place!!!! The owner is very responsive and friendly and when requested a few things she was very accommodating and helpful! Also, the area is very peaceful and the home was wonderful all around-we will definitely rest this home again for more skiing and hiking and in Summer for lake trips! Thank you again Mattis for opening up your home to us!”

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

Lovin' Life Deep Creek - Luxury home w/ lake views
SUPERHOSTEntire chalet
Lovin' Life Deep Creek - Luxury home w/ lake views
Price:$367 CAD/night
Incredible Cozy Cabin Immersed in Nature
SUPERHOSTEntire cabin
Incredible Cozy Cabin Immersed in Nature
Price:$247 CAD/night
3-Bedroom Renovated Lakeside Townhouse Near Wisp
SUPERHOSTEntire townhouse
3-Bedroom Renovated Lakeside Townhouse Near Wisp
Price:$310 CAD/night
May the forest be with you
SUPERHOSTEntire cabin
May the forest be with you
Price:$304 CAD/night
A "Sweet Retreat" at Deep Creek & Wisp Ski Resort
SUPERHOSTEntire chalet
A "Sweet Retreat" at Deep Creek & Wisp Ski Resort
Price:$232 CAD/night
*Secluded Forest* Cozy*Deck Fireplace*Hot Tub*Wifi
SUPERHOSTEntire house
*Secluded Forest* Cozy*Deck Fireplace*Hot Tub*Wifi
Price:$347 CAD/night
Family friendly Cozy, private dock Sparkling CLEAN
SUPERHOSTEntire house
Family friendly Cozy, private dock Sparkling CLEAN
Price:$343 CAD/night
Famous Lakefront Home Deep Creek Lake
Entire house
Famous Lakefront Home Deep Creek Lake
Price:$1,136 CAD/night
The View
Entire guest suite
The View
Price:$102 CAD/night
One of a Kind - Lake Farm Suite w Private Entrance
SUPERHOSTEntire guest suite
One of a Kind - Lake Farm Suite w Private Entrance
Price:$109 CAD/night
Molly
SUPERHOSTEntire cabin
Molly
Price:$167 CAD/night
R & R Retreat
SUPERHOSTEntire chalet
R & R Retreat
Price:$301 CAD/night
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