Oakland vacation rentals

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Top-rated vacation rentals in Oakland

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Guest favorite

Home in Oakland

4.95 out of 5 average rating, 192 reviews

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, 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. HOT TUB by FIREPLACE on deck. CARC membership, lots of firewood and supplies.

Dec 10 – 17

ﺩ.ﺇ1,889 per night

Guest favorite

Tiny home in Oakland

4.98 out of 5 average rating, 168 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".

Sep 9 – 16

ﺩ.ﺇ488 per night

Guest favorite

Chalet in Oakland

4.96 out of 5 average rating, 248 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!

Nov 8 – 15

ﺩ.ﺇ1,615 per night

Guest favorite

Guest suite in Swanton

4.8 out of 5 average rating, 198 reviews

The View now with Wi-Fi

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!!

Mar 1 – 8

ﺩ.ﺇ291 per night

Guest favorite

Home in Oakland

4.82 out of 5 average rating, 146 reviews

General Kelly Guesthouse

Welcome to our guesthouse! This place is perfectly situated for those who love the outdoors. Long walks down the lane, the rolling mountains and fields, and quiet nights can be yours to enjoy. The views are truly spectacular and can be enjoyed from the front porch in the summer or the enclosed sunroom on those chilly mornings. This house is perfect for couples or families wanting a quiet space to relax and recharge. Quaint and comfortable, each room is clean and personally decorated.

Mar 21 – 28

ﺩ.ﺇ553 per night

Guest favorite

Cabin in Oakland

4.98 out of 5 average rating, 158 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.

Nov 26 – Dec 3

ﺩ.ﺇ503 per night

Guest favorite

Cabin in Deep Creek

4.98 out of 5 average rating, 105 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.

Feb 28 – Mar 7

ﺩ.ﺇ458 per night

Guest favorite

Tiny home in Accident

4.96 out of 5 average rating, 166 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!

Sep 7 – 14

ﺩ.ﺇ593 per night

Guest favorite

Guest suite in Terra Alta

4.94 out of 5 average rating, 201 reviews

Home on the mountain

Beautiful view of the river valley andthe town of Kingwood West Virginia. Large kitchen with pots and pans. You have your own entry with open floor plan. Main house is above. There are lot’s of windows to view the picturesque valley. With vintage decor and a gas fireplace which makes for romantic setting. From sunrise to sunset the view is incredibly beautiful. 45 min from WVU 2 miles from Camp Dawson Black water falls 40 minutes. Wi-Fi available

Sep 21 – 28

ﺩ.ﺇ331 per night

Guest favorite

Cabin in Oakland

4.95 out of 5 average rating, 188 reviews

Lakehound Lodge - lake view, pet friendly

Cozy cabin in the middle of all that Deep Creek Lake area has to offer! Enjoy a dip in the hot tub by the fire with peekaboo lake views under twinkle lights. This three level cabin boasts a bedroom and bathroom on each level, two wood burning fireplaces, two living rooms, and an enclosed side porch with hot tub. Pets welcome for a fee. Close to the lake, Wisp, parks, golfing, fishing, and much more! Follow insta @lakehoundlodge

Feb 10 – 17

ﺩ.ﺇ1,318 per night

Guest favorite

Cabin in Davis

4.97 out of 5 average rating, 270 reviews

The Davis Loft - The Best Location in Davis!

The Davis Loft is the closest home rental to Blackwater Falls and is within walking distance to all that Davis has to offer. The loft has all the modern touches you would expect but still retains the right amount of rustic nostalgia that blends in so perfectly with the culture and landscape of the magnificent Canaan Valley. Have a front row seat to one of the most beautiful places in eastern North America.

Sep 5 – 12

ﺩ.ﺇ422 per night

Guest favorite

Home in Swanton

4.97 out of 5 average rating, 186 reviews

Bev's House at Sunny Meadows

Looking for a place to stay that is quiet and relaxing, but also close to many outdoor activities? Bev's House at Sunny Meadows is just that! Located just minutes from several state parks that offer boating, fishing, kayaking, swimming, hiking and biking, there's always plenty to do. Bev's House offers a quiet place with spectacular mountain views to escape the rush and noise of everyday life.

Jun 5 – 12

ﺩ.ﺇ625 per night