
Apartment vacation rentals in Oakland
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Top-rated apartment rentals in Oakland
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Riverview Suite
Come stay at our unique three-bedroom suite adjacent to the Youghiogheny River, white water rafting, and the Kendall Trail. Thoughtfully designed with many amenities for your comfort and located upstairs for a peaceful river view. There is a big private and free parking lot in the back for your stay. We are in walkable length to local restaurants, gas stations, bank, pub, post office, vehicle mechanic, park, pharmacy, and good people. Come stay and be our guests. Deep Creek Lake 8 miles away.

Pit Stop Penthouse
Room for the whole family at this newly renovated, comfortable abode located above a motorsports store and garage (closed on weekends). A perfect pit stop in the Canaan Valley for skiing, hiking and all your outdoor adventures. Large balcony with hot tub and view. Located steps from a brewery and restaurant. Nice walk or short drive to downtown Thomas, within 10-minute drive of Canaan Valley State Park, Blackwater Falls State Park, Timberline Mountain Ski Resort, and the beloved town of Davis.

Coopers Rock Retreat
Industrial farmhouse studio apartment nestled in the hills of West Virginia. Located just 15 minutes to downtown Morgantown and 5 short minutes away from Coopers Rock State Forest. Spectacular landscape views from dusk to dawn and breathtaking star gazing on clear nights. Guests have their own private entrance to come and go as they please, a full kitchenette, large bathroom with walk-in shower, queen size bed, and an extra long single futon. Guests need to be at least 21 years of age book.

Dandy Flats - The Quaintrelle
Tucked inside the oldest historic buildings on the main drag in Thomas and adorned with 135-year old plaster walls, original woodwork, encaustic tile and purple marble - this tastefully styled flat is for those looking for the transportive experience historic buildings deliver. With espresso, galleries, live music, shops, food, and drinks steps away, you have the forests and a tiny cityscape just steps out your door. This apartment is offered at the Dandy Flats - a lovingly restored Inn.

Lovin' Lake Life - No Wake Zone Unit 3 of 3
Enjoy this cozy, clean, lakeside hotel-like efficiency. Perfect place to relax after enjoying outdoor fun in the Laurel Highlands! Walk out your door to the Youghiogheny Lake boat/kayak launch, fishing and picnic area. Kayak, paddle board and pontoon boat rentals in walking distance. Each unit has a private entrance and access to an outdoor common area porch. Under 30-minute drive to local attractions: Ohiopyle Park, biking/hiking trails, winery, casino, Deep Creek Lake and more! No pets

Stunning Historic 3-Bedroom Apt Thomas River View
Beautifully renovated 1890's historic apartment overlooking Blackwater River in central Thomas! Gourmet kitchen/extra large deck/stylish front porch/large master private bath. Go back in time with all modern conveniences - best location! Right out your door-art galleries, specialty boutiques, Tip Top Coffee, famous Purple Fiddle for entertainment, stroll along Black Water River, walk to hiking trails, 15 min drive to Timberline Mountain/Canaan State Park/Whitegrass! Non-smoking property

Alice's Place
Welcome to Alice’s Place your little retreat in the Appalachian Mountains! You may wake up to the smell of our smoker cooking something delicious! Maybe you will get a sample to try our bbq sauce that awaits you! Relax by the outdoor fire pit and make some s’more’s, or cozy up by the indoor fireplace with your favorite book. Enjoy a walk at the beautiful Cathedral State Park, just a 5 min drive. The smallest church in 48 states is just a 13 min drive. Such a fun, unique place.

Romantic Getaway with Beautiful Lake Views
Relax and enjoy this cozy condo with beautiful Deep Creek lake and mountain views from the living room or while relaxing on the hanging swing on the outdoor deck while enjoying your morning cup of coffee. Conviently located within walking distance to a popular restaurant, coffee shop and kayak rentals. Perfectly positioned in central Deep Creek with a short drive to everything including the Wisp Ski Resort, shops, multiple state parks, arcade, mini golf and a movie theater.

Dandy Flats - The Nonchalant
Located in a historic building on the main drag and adorned with 135-year old hardwood floors, original woodwork, local art, huge rain shower, and forest views - this tastefully styled flat feels like being transported to a 19th century boarding house. With espresso, galleries, live music, shops, food, and drinks steps away, you have the forests and a tiny cityscape just steps out your door. This apartment is offered at the Dandy Flats - a lovingly restored Inn.

The Nest near Deep Creek
Kick back and relax in this calm, stylish space. Brand new, beautiful one bedroom apartment above a detached garage just 5 miles from Deep Creek Lake. Beautifully designed space with craftsman quality large kitchen, king size neo-industrial walnut bed, live-edge vanity and wall cap, articulating lamp, all made by local craftsman. Leather pull out couch with queen bed sleeps two extra guests. Relax by the fire pit and listen to the birds in the woods.

Over the Top - Entire Apartment In Thomas
Be on top of the Thomas vibes in this centrally located spacious apartment perched above the new TipTop Coffee Shop location. Wake up to the smell of freshly ground coffee, stroll down Front Street, take in the arts and culture of the galleries, Purple Fiddle music venue and eclectic shops. The Blackwater Canyon rail trail is right outside your door step, and hundreds of miles of hiking, biking and ski trails call you to adventure.

Cozy Sage Retreat (Renovated 1BR Apartment)
Unwind in the heart of Oakland, Maryland, at this thoughtfully renovated one-bedroom (King Bed), first floor apartment retreat where modern comfort meets mountain-town charm. With calming sage-green tones, stylish furnishings, and a spa-inspired bathroom, this cozy apartment is the perfect home base for couples, solo travelers, remote workers, and outdoor enthusiasts exploring Deep Creek Lake and the surrounding mountains.
Popular amenities for Oakland apartment rentals
Weekly apartment rentals

The Nest near Deep Creek

Alice's Place

Riverview Suite

Private Unit on Farm with Kitchen & Balcony

The Blue Door in The Flats

Coopers Rock Retreat

Loft apartment

Main St Apt w/ Pool Table & Sauna in Westernport!
Private apartment rentals

Lake Happiness - No Wake Zone Unit 1 of 3

Large 2-bdrm apt. Walking distance to everything

Corner Pocket in The Flats

Barn Suite with Kitchen, Jacuzzi & Fireplace

Pool Table & Shared Sauna! Potomac River Basecamp

In historic downtown, 2 minute walk to everything!

Stay with us in comfort - Upstairs apartment.

Private Unit on Peaceful Farm, Convenient to Lake
Apartment rentals with a hot tub

Charming 3BR Condo - HOT TUB - Wisp View - McHenry

Pit Stop Penthouse

Private Unit on Farm with Kitchen & Balcony

Oakland Home Efficiency Apartment
Quick stats about apartment rentals in Oakland

Nightly prices starting at
Oakland vacation rentals start at G$12,547 GYD per night before taxes and fees

Verified guest reviews
Over 190 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Oakland rentals

4.8 Average rating
Oakland stays are highly rated by guests—averaging 4.8 out of 5!
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- Fallingwater
- Wisp Resort
- Seven Springs Mountain Resort
- Timberline Mountain
- Ohiopyle State Park
- Canaan Valley Resort & Conference Center
- Blackwater Falls State Park
- Canaan Valley Ski Resort
- White Grass
- Tygart Lake
- West Virginia University
- Rock Gap State Park
- Deep Creek Lake State Park
- Swallow Falls State Park
- Laurel Hill State Park
- Coopers Rock State Forest
- Fort Necessity National Battlefield
- Lodestone Golf Course
- Audra State Park
- Smoke Hole Caverns
- Western Maryland Scenic Railroad





