
Apartment holiday 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.

Vintage Studio Apartment
My place is on historic Second St. Walking distance to downtown shops, farmer's market, library. Hospital and more. It is a 3rd floor apt with no elevator. It has beautiful views of nature. It is small, but comfortable. It has a small bathroom, shower only, kitchen and closet. Mini splits with air and heat as well as ceiling fans in livingroom/bedroom and kitchen. Take your stroll down nearby walking paths, parks and short drive to waterfalls, Deep Creek Lake and eateries. On Autumn Glory route

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

Country Home
Relax with family, friends, or enjoy a solo retreat at this peaceful place to stay in the country. Chestnut House was built in the early 1940s, with Wormy Chestnut wood everywhere! It is a unique home, with an apartment built over a garage / wood working shop.. then connected to the main house later. This space available to rent is separate and fully functional from the main house where we live. Enjoy 2 bedrooms, 1 bathroom, full kitchen and living area.. along with the large outdoors!

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.

Corner Pocket in The Flats
A creative flat in the heart of Thomas, WV. This apartment is located central to our town providing a minutes walk to the businesses of Front St. Five galleries, TipTop (WV's best Coffeeshop), retail, restaurants, and the famed Purple Fiddle music venue are all right out the door. The space is simple, functional, thoughtful, clean and carefully decorated from local art spaces, Bloom and Creature in Thomas (in the same building).

Riverside Loft with Huge Deck on GAP Trail
The new, spacious Loft sits on the banks of the Casselman River on the top floor of the former Confluence high school. The loft sleeps up to 8. It features an open floor plan, large windows and enormous deck with a great view of the river, mountains and town. The building is powered by solar panels. Easy access to town and just off the GAP bike trail. The perfect location for recreating and relaxing in the Laurel Highlands.
Popular amenities for Oakland apartment rentals
Weekly apartment rentals

The Nest near Deep Creek

Lake Happiness - No Wake Zone Unit 1 of 3

Alice's Place

Riverview Suite

Private Unit on Farm with Kitchen & Balcony

Lucky Duck * New LIsting*

Romantic Getaway with Beautiful Lake Views

Loft apartment
Private apartment rentals

Lake Happiness - No Wake Zone Unit 1 of 3

Barn Suite with Kitchen, Jacuzzi & Fireplace

Pool Table & Shared Sauna! Potomac River Basecamp

In historic downtown, 2 minute walk to everything!

2 Bed 1 Bath Apt. by Wisp Resort & Deep Creek Lake

Stay with us in comfort - Upstairs apartment.

Charming 1-bdrm with balcony, Close to Everything.

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

Private Unit on Farm with Kitchen & Balcony

Oakland Home Efficiency Apartment

Pit Stop Penthouse

Furnished Apartment inTerra Alta

Splendid dog-friendly home with hot tub, deck
Quick stats about apartment rentals in Oakland

Nightly prices starting at
Oakland holiday rentals start at $103 NZD 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!
Destinations to explore
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- Wisp Resort
- Fallingwater
- Timberline Mountain
- Seven Springs Mountain Resort
- Ohiopyle State Park
- Canaan Valley Resort & Conference Center
- White Grass
- Canaan Valley Ski Resort
- Blackwater Falls State Park
- Tygart Lake
- Laurel Hill State Park
- Swallow Falls State Park
- Rock Gap State Park
- West Virginia University
- Deep Creek Lake State Park
- Coopers Rock State Forest
- Hidden Valley Resort
- Fort Necessity National Battlefield
- Lodestone Golf Course
- Smoke Hole Caverns
- Audra State Park
- Western Maryland Scenic Railroad




