Holiday rentals in Oakland

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Top-rated holiday rentals in Oakland

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

Guest favourite
Home in Oakland
Cozy&Private|HotTub|CARC|Firewood|Essentials|5 Str
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.
27 Jan – 3 FebIndividual Host,
£491 per night
4.94 out of 5 average rating, 193 reviews
Guest favourite
Cabin in Oakland
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. Pet 50extra
1–8 MayIndividual Host,
£232 per night
4.9 out of 5 average rating, 351 reviews
Guest favourite
Tiny home in Oakland
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".
3–10 MayIndividual Host,
£113 per night
4.98 out of 5 average rating, 168 reviews

Popular amenities for Oakland holiday rentals

Stay near Oakland's top sights

Walmart Supercenter75 locals recommend
Browning's Shop n Save48 locals recommend
El Canelo Restaurant13 locals recommend
Farmers Market44 locals recommend
China Wok5 locals recommend
Englander’s Antiques and Grill46 locals recommend

Other great holiday rentals in Oakland

Guest favourite
Cabin in Maysville
Modern cabin in Dolly Sods w/ sauna & EV charger
5–12 Feb
£288 per night
5.0 out of 5 average rating, 133 reviews
Guest favourite
Cabin in Oakland
Mountain Escape - Hot Tub, Game Room, Fire Pit
13–20 OctIndividual Host,
£291 per night
4.86 out of 5 average rating, 125 reviews
Guest favourite
Townhouse in Oakland
Lake view condo with wood fireplace!
29 Sept – 6 Oct
£164 per night
4.9 out of 5 average rating, 155 reviews
Superhost
Home in Oakland
The Wise Quack - A Taste of Deep Creek Lake!
30 Apr – 7 MayIndividual Host,
£80 per night
4.87 out of 5 average rating, 60 reviews
Guest favourite
Cottage in Oakland
Cheerful cottage minutes from Wisp and Deep Creek
1–8 Jan
£126 per night
4.92 out of 5 average rating, 52 reviews
Guest favourite
Holiday home in Oakland
1-Bedroom near Deep Creek Lake with Mountain View
15–22 Jun
£111 per night
4.93 out of 5 average rating, 29 reviews
Guest favourite
Home in Oakland
Lovers Loft Lodge on the Lake, NO cleaning Fee!
2–9 Nov
£118 per night
4.98 out of 5 average rating, 43 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
10–17 Jun
£131 per night
4.85 out of 5 average rating, 40 reviews
Superhost
Cabin in Oakland
~Cabin on a Mountain Sanctuary w/pond
27 Jun – 4 JulIndividual Host,
£91 per night
4.81 out of 5 average rating, 58 reviews
Guest favourite
Tiny home in Swanton
Tiny House-Dream Catcher Cabin #2
10–17 Sept
£82 per night
5.0 out of 5 average rating, 12 reviews
Guest favourite
Tiny home in Mineral County
Glamping in a Creekside Aframe
21–28 Jan
£150 per night
4.96 out of 5 average rating, 93 reviews
Guest favourite
Cabin in Oakland
Cabin in the Woods
1–8 Sept
£166 per night
5.0 out of 5 average rating, 27 reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Garrett County
  5. Oakland