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Apartment vacation rentals in Oakland

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Top-rated apartment rentals in Oakland

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

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Guest favorite
The kitchen features white cabinetry and modern appliances, including a stove and refrigerator. A wooden bar with stools offers a casual dining space. Natural light enters through the door leading outside, illuminating the warm wood accents on the walls and floor.
Apartment in Friendsville
4.93 out of 5 average rating, 195 reviews

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.

Apartment in Westernport
4.75 out of 5 average rating, 4 reviews

Pool Table & Shared Sauna! Potomac River Basecamp

Walk to Local Eats | Private Patio w/ Dining Space | Near Year-Round Recreation High-altitude fun meets valley-floor comfort at this Westernport vacation rental. The apartment places you in the heart of North Branch fishing territory, and offers easy highway access to scenic hikes and Wisp Resort’s powdery slopes. After an adventurous day, unwind with a billiards battle, enjoy dinner on the private patio, or relax your muscles in the sauna. Let the mountains show you a good time — book today!

A cozy living area features a navy blue sofa adorned with decorative cushions. A wooden coffee table sits on a patterned rug, while a small dining table with two chairs is positioned near a vase of sunflowers. A ceiling fan is mounted above for comfort.
Apartment in Oakland

Downtown Healing Retreat Aptmt

Take it easy at this unique and tranquil getaway. One-bed room apartment at second floor of a multi-unit building in the heart of downtown Oakland. Walking distance to downtown museums, historic railroads and train station. walk half a block to multiple restaurants, bakeries, gift shops and hardware stores. The apartment is completely newly renovated with all new flooring, kitchen and bathroom. All towels, sheets and 100% organic cotton. Concierge healing services acupuncture available.

Top guest favorite
A vibrant sunset casts shades of pink and orange across the sky, reflecting on the calm waters of the lake. Silhouettes of trees and a bridge are visible in the background, enhancing the serene outdoor landscape.
Apartment in Addison
5 out of 5 average rating, 10 reviews

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

Top guest favorite
The entrance features a green door with glass panels, accompanied by a welcome mat that reads 'hello.' A decorative sign displaying 'Alice's Place' is mounted on the wall. A potted plant with red flowers and a wooden rocking chair are positioned nearby.
Apartment in Aurora
5 out of 5 average rating, 47 reviews

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.

Top guest favorite
Apartment in Oakland
4.89 out of 5 average rating, 19 reviews

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.

A living area features a comfortable leather couch with decorative cushions and an accent chair. Light-colored walls are complemented by a contrasting turquoise wall, and framed artwork is displayed above the seating area. Natural light enters through a doorway leading outside.
Private room in Oakland
4.57 out of 5 average rating, 7 reviews

Oakland Home Efficiency Apartment

This efficiency apartment is great for a single person or a couple. The steel door in the bathroom leads to the garage and the shared washer and dryer. The freezer in the garage under the stairwell is only for the convenience of those occupying the efficiency apartment. All other games, table tennis, chairs etc., in the garage, are to be shared. The upper balcony and hot-tub can be shared with those occupying the upper level. Respecting each group's privacy is expected.

Apartment in McHenry
New place to stay

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

Welcome to Chillaxin Chillaxin is a 3-bedroom, 3.5-bathroom condo that sleeps up to 8 guests - and it earns its name from the moment you walk in. With a bubbling hot tub, a wood-burning fireplace in the main living room, and sweeping views of the woods and Wisp Resort, this is the kind of place where plans get replaced with deep breaths and long evenings on the deck. Whether you're here for the slopes, the scenery, or simply each other, Chillaxin delivers.

Top guest favorite
A spacious living area features a large leather sectional sofa with accent pillows, paired with rustic wooden coffee tables. A sleek entertainment center holds a wall-mounted TV, while framed landscape artwork adorns the walls, adding a touch of color to the room.
Apartment in Accident
5 out of 5 average rating, 160 reviews

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.

Apartment in Oakland
4.82 out of 5 average rating, 84 reviews

Large 2-bdrm apt. Walking distance to everything

Great Location! 2 bdr/1 ba large and charming apt., Walking distance (within 1/5 mile to Garrett Memorial Hospital and historic district including antique shops, dining, farmers market, train station, library, hospital, courthouse, pharmacy). Short drive to Deep Creek Lake and Wisp Resort area, Swallow Falls State Park, and many more!. Large and charming 2-bedroom, fully remodeled, 1 bathroom with shower tub, large closets in each bedroom.

Superhost
Apartment in Oakland
New place to stay

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.

A comfortable living area is displayed, featuring a golden-brown upholstered sofa adorned with colorful throw pillows. A wooden coffee table sits in front, accompanied by a cozy armchair. Floral artwork is visible on the walls, and natural light enters through wooden blinds.
Apartment in Rowlesburg
4.83 out of 5 average rating, 6 reviews

Stay with us in comfort - Upstairs apartment.

Take it easy at this unique and tranquil getaway. Rowlesburg is tucked away in the Cheat River Valley surrounded by majestic hills, rising on all sides from the banks of the beautiful Cheat River. October is Autumn Glory month. The Downtown Rowlesburg Historic District was listed on the National Register of Historic Places. There are many interesting and fun things to do and see in town, in Preston County and beyond.

Popular amenities for Oakland apartment rentals

Quick stats about apartment rentals in Oakland

  • Nightly prices starting at

    Oakland vacation rentals start at G$12,531 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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