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

Private|LAKE|Waterfalls|Firewood|Comm. PoolHot Tub

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.

Mar 25 – Apr 1

G$108,745 GYD 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".

Dec 28 – Jan 4

G$27,683 GYD 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!!

Nov 8 – 15

G$16,401 GYD 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.

Jun 5 – 12

G$26,797 GYD 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.

Dec 13 – 20

G$28,550 GYD per night

Guest favorite

Tiny home in Hambleton

4.97 out of 5 average rating, 148 reviews

Cozy Camper on the Rail Trail

Unique, dog-friendly camper-to-tiny home conversion. Wake up to amazing views with mountains in every direction. The Allegheny Highlands rail trail greets you as you step out the front door. No pet fees! Perfect for those looking for a peaceful and safe location, just off the beaten path. Surrounded by the Monongahela Forest, and the Cheat River, this valley is an outdoor recreation paradise. Rustic and simple, the guest house offers you what you need for a comfy stay.

Oct 12 – 19

G$18,713 GYD per night

Guest favorite

Guest suite in Accident

4.98 out of 5 average rating, 240 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!

Mar 4 – 11

G$21,339 GYD 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.

Jan 31 – Feb 7

G$26,010 GYD per night

Guest favorite

Tiny home in Accident

4.95 out of 5 average rating, 169 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 8 – 15

G$33,657 GYD per night

Guest favorite

Guest suite in Terra Alta

4.94 out of 5 average rating, 202 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

Aug 25 – Sep 1

G$18,812 GYD 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 20 – 27

G$69,594 GYD per night

Guest favorite

Cabin in Davis

4.97 out of 5 average rating, 271 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.

Apr 17 – 24

G$23,632 GYD per night