Oakland vacation rentals

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Top-rated vacation rentals in Oakland

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

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Guest favorite

Cabin in Oakland

4.95 out of 5 average rating, 203 reviews

Private/Tubing/Pool Acc/Deck Fireplace/Many Extras

Business Name: LAZY BEAR LODGE AT DEEP CREEK LAKE Need some quality time away but want to avoid crowds & still be close to everything at the Lake? Secluded, private and located on 3 acres in a serene forest of hemlock trees & boulders, this natural space is calming & architecturally pleasing to the eye and soul! Let your cares slip away with the smell of a real wood fire, rustic décor, warm color paints, stone and wood. HotTub by fireplace on deck. CARC membership, lots of firewood and supplies.

Guest favorite

Tiny home in Oakland

4.97 out of 5 average rating, 182 reviews

The Original Hob

We have the Original Hob and Molly (separate listing) overlooking our creek at the point of 7 little waterfalls for your sleeping and hangout pleasure! A shared sweet kitchen and bath completes the 3 small structures. Full bath plus an outdoor shower makes for great accommodations. We're within 5 miles of State Parks and Deep Creek Lake. Come see the Garrett County stars, hear the creek and birds and be a million miles from where you are. Friendly dogs are welcomed -see "other things to note".

Guest favorite

Cabin in Oakland

4.99 out of 5 average rating, 107 reviews

HotTub-FirePit-8MintoWisp-Arcade-4BD-NoCleaningFee

Jamesons Cabin: Spacious and pet-friendly, 8 mins from Wisp Resort - Sleeps 12 with 3 bedrooms + loft (4th bedroom), and a full sofa bed. - 75 inch tv over a cozy wood burning fireplace - Hot tub with a bar! - 4-player arcade, karaoke, and darts for entertainment - Putterball golf to show off your skills - A galaxy lamp for kids to sleep under the stars - Full kitchen, coffee bar and grill for delicious meals - 48W EV charger We want to help you make unforgettable memories. Reach out today!

Guest favorite

Chalet in Oakland

4.96 out of 5 average rating, 280 reviews

Private (5 Star!) Lake Access Chalet w/ Hot Tub

Lake Forest Chalet is located on a private, dead end secluded lane with very little traffic. Bring your bikes and strollers for a stroll down the lane where kids can play and enjoy themselves without the worry of traffic rushing by. A short walk to the lake! Boat slip, Hot Tub, Firepits, and awesome outdoor area w/ Playset, Cornhole, and horseshoes. 5G internet & desk space in loft! Garage is off limits to guests, for owners use only. Disinfecting deep clean performed before every stay!

Guest favorite

Guest suite in Swanton

4.81 out of 5 average rating, 221 reviews

The View

Spacious, clean, modern basement efficiency apartment. Private entrance, private bath w/shower, private kitchenette with full size fridge & microwave (no stove), 1 queen size bed. Pool table, bar area and living room space with large TV equipped with satellite service. More space than a hotel room. View of Deep Creek Lake from front lawn in the distance, 11 Miles to Wisp, 6 miles to Deep Creek State Park and 1 mile to Thousand Acres Golf Course. NO Smoking, No Pets. We now have WIFI!!

Guest favorite

Cabin in Oakland

4.98 out of 5 average rating, 168 reviews

SUGARBUSH - Sweet Serenity Tiny House

Welcome 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. AGE REQUIREMENT to book this space is 25+. 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.

Guest favorite

Guest suite in Accident

4.98 out of 5 average rating, 249 reviews

New! The Butterfly Suite at Enchanted Table Meadow

Minutes from Wisp Ski Resort & Deep Creek Lake! Come as you are & take a seat at nature’s table under the canopy of stars. Embrace the wooded ambiance and meadow views from our 825 sq. ft suite as you melt your cares away in front of the fireplace. Located between I-68 and Deep Creek Lake/Wisp. Our hope is to provide a serene landscape where you can find peace and rest through nature. Our setup works well for business travelers & as a couple's romantic escape!

Guest favorite

Cabin in Deep Creek

4.97 out of 5 average rating, 117 reviews

Boulder Ridge Cabin, close to Deep Creek, Maryland

Boulder Ridge Cabin is surrounded by woods, but within 15 minutes of Deep Creek Lake, swimming, boating, hiking, shopping, restaurants, Wisp Resort with skiing, snowboarding, mountain coaster, whitewater rafting at Adventure Sports Center International, rock climbing, hiking. Swallow Falls State Park and Herrington Manor State Park are about 15 minutes drive. Piney Mountain State Forest is within walking distance. Mountain biking and fishing are also close by.

Guest favorite

Tiny home in Accident

4.96 out of 5 average rating, 225 reviews

Romantic Getaway In The Pines

Looking for a romantic stay for you and your significant other??Then this unique romantic cabin is the perfect place for you! Nestled in the mountains near Deep Creek Lake, you can enjoy the fresh mountain air from the deck or hot tub with peaceful, scenic views. Propane and wood fireplaces outside along with and outdoor tv that you can watch from the hot tub! Soak in the beauty of Garrett County and all Deep Creek Lake has to offer. Hope to see you soon!

Guest favorite

Cottage in Oakland

4.94 out of 5 average rating, 214 reviews

Pet-Friendly Cozy Home w/Hot Tub & Fire Pit

Wisp Away to this lovely cozy home. Located walking distance from Deep Creek Lake and only a short drive to Wisp Resort. Centrally located near all the area's amenities including parks, restaurants, golfing, boating, beaches and so much more. This home features a queen-sized bed, a full bathroom, and a kitchenette. Relax at home by the firepit or soaking in the hot tub. Pets are welcome. We look forward to sharing our cabin with you and your fur baby.

Guest favorite

Cottage in Oakland

4.94 out of 5 average rating, 105 reviews

Cheerful cottage 2 minutes from Deep Creek Lake

Just the right size and location for enjoying all Deep Creek Lake has to offer- including scenic hikes on many nearby trails, skiing at Wisp, or just enjoying time on the lake amongst bustling lake life. Then retreat back to our quaint cottage and enjoy time together. You will love our place because of its coziness, location, cleanliness, affordability and perfect size for a single family stay. *bathroom is in the bedroom *we have parking for a boat*

Guest favorite

Cottage in Oakland

4.92 out of 5 average rating, 143 reviews

Pet friendly-Cottage in the Woods

Tucked conveniently between Swallow Falls State Park and Deep Creek Lake, this recently renovated 2 bd cottage has everything you need for a weekend getaway or a much needed week(s) long vacation! Inside you will find a completely stocked kitchen, open living/dining area, full size bathroom, 2 bedrooms and a cozy nook with sleeper sofa and desk. Relax and unwind in the spacious backyard or charming balcony. *pets stay free