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Apartment vacation rentals in Oakland

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Popular amenities for Oakland apartment rentals

Weekly apartment rentals

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, 106 reviews

New! The Nest near Deep Creek

CherylRating, 5 stars1 day ago
This place was excellent a great find. Diane was pleasant she greeted us with a smile and knew me by name. We arrived early and wasn’t a problem. To add to everything she left us some fresh eggs in the refrigerator. One of the cleanest places I ever stay in. Thank you Diane continue to the person God designed you to be and I will definitely be back.
Guest favorite
A cozy living area features a dark sectional couch complemented by a patterned area rug. A small table is positioned beside the couch, and a television rests on a wooden console, creating a comfortable space for relaxation.
Apartment in Frostburg
4.9 out of 5 average rating, 173 reviews

The GreyLoo

TrentRating, 5 stars1 week ago
This a great place. The living room is very cozy, and the bedroom has a lot of space. Located in a nice quiet neighborhood. This was a very good deal, especially for the price!
Superhost
A spacious living area is shown with large windows offering views of trees outside. A comfortable sofa with decorative pillows faces a coffee table, while a sitting area includes two chairs and a small table. Natural light fills the room, enhancing the open layout.
Apartment in Confluence
4.95 out of 5 average rating, 21 reviews

Modern, spacious Loft with River View just off GAP

Hui-MinRating, 5 stars4 months ago
Kara’s loft is very modern and functional. It’s both spotlessly clean and welcoming. Our two families of 7 enjoyed our two-night stay. Visited the famous Fallingwater, and made good use of the well-equipped kitchen for warm family gatherings. Thank you, Kara, for the opportunity to stay in this unique unit.
Guest favorite
The living area features a vibrant blue sofa adorned with decorative cushions. A cozy patterned chair complements the space. A wooden coffee table is set with a tray. Natural light enters through a large window, framed by sheer white curtains, while wooden paneling adds warmth.
Apartment in Friendsville
4.94 out of 5 average rating, 147 reviews

Riverview Suite

JulieRating, 5 stars2 days ago
Wandas place was great and nice and clean This location is only a short drive to deep creek and surrounding areas. it is very walkable and my dogs enjoyed the nearby trail. Wanda allowed my 2 dogs and was very responsive and let is check in a tad earlier. Wanda put a lot of time into the cute and welcoming decor in the apartment and it was very clean. Thanks for a great stay.
Superhost
The living room features large windows that provide natural light, with decorative curtains framing the space. A coffee table sits centered on a patterned area rug, surrounded by comfortable seating including leather recliners and a sofa. A piano adds a touch of character to the room.
Apartment in Oakland
4.83 out of 5 average rating, 81 reviews

Large 2-bdrm apt. Walking distance to everything

AllenRating, 5 stars6 months ago
Older, very roomy apartment in a quiet neighborhood, just the way we like it. Carmen was very responsive to all our inquiries. Would stay again.
Top guest favorite
A warm wood fireplace stands as a focal point, complemented by a mounted TV above it. Shelves built into the wall display curated items, while the room features hardwood flooring and a doorway leading outside.
Apartment in Oakland
4.91 out of 5 average rating, 120 reviews

Private Unit on Farm with Kitchen & Balcony

KeeshaRating, 5 stars6 months ago
Our stay on the farm was peaceful and quiet. The view was amazing. The suite was clean and private. Kam was super responsive to an issue we had with the jacuzzi tub and was there within 15 minutes along with her maintenance man. Definitely recommended Haley Farm if you desire peace and that down on the farm feel!
Top guest favorite
A corner seating area features two plush gray armchairs beside a small round table. Natural light enters through a window adorned with sheer curtains, while a decorative plant and a cozy blanket add subtle touches to the space.
Apartment in Salisbury
4.96 out of 5 average rating, 126 reviews

Ord St Inn Unit Two, spacious 2nd floor apartment

ChristopherRating, 5 stars1 week ago
Absolutely 100% Top notch! Immaculately clean, quiet, comfortable and Joe is a great host. I can't say enough about how perfectly this was setup.
Superhost
The living room showcases a combination of wooden beams and warm wood tones in the ceiling and walls. A leather sofa and a cushioned chair are arranged around a small coffee table. Natural light fills the space, highlighting a potted plant and a sliding glass door leading to an outdoor deck.
Apartment in Confluence
4.77 out of 5 average rating, 31 reviews

"Sweet Suite'

ThomasRating, 5 stars9 months ago
We loved the place, such an awesome little community, already planning our return.

Private apartment rentals

Superhost
The living room features large windows that provide natural light, with decorative curtains framing the space. A coffee table sits centered on a patterned area rug, surrounded by comfortable seating including leather recliners and a sofa. A piano adds a touch of character to the room.
Apartment in Oakland
4.83 out of 5 average rating, 81 reviews

Large 2-bdrm apt. Walking distance to everything

AllenRating, 5 stars6 months ago
Older, very roomy apartment in a quiet neighborhood, just the way we like it. Carmen was very responsive to all our inquiries. Would stay again.
Superhost
A comfortable living area features a cozy sofa positioned near a decorative fireplace. A TV is placed on a wooden stand, with a lamp casting soft light. A window dressed with light curtains allows natural light to illuminate the space.
Apartment in Oakland
4.89 out of 5 average rating, 46 reviews

Barn Suite with Kitchen, Jacuzzi & Fireplace

ShellyRating, 5 stars6 months ago
Kam accommodated us on short notice as we had to come up quickly due to a family member being hospitalized. The place is so peaceful and on beautiful grounds. It was easy to find and a Tesla charger was outside our door. I will stay here again!
Superhost
A spacious living room is presented, featuring comfortable seating with brown sofas arranged around a coffee table. A large plant adds a touch of greenery, while artwork and decorative elements are visible on the walls. Natural light filters in through a nearby window.
Apartment in Confluence
4.74 out of 5 average rating, 19 reviews

"Home Sweet Home Suite" Come Sit on Our Porch!

LynneRating, 5 stars11 months ago
Very convenient to the GAP for biking. We had a couple of minor issues, but these were addressed quickly. The beds were comfortable.
A friendly dog stands in the foreground with a gravel shore, smiling. Behind, a wooden dock stretches into the calm water surrounded by trees. The bright sky overhead highlights the natural beauty of the area.
Apartment in Swanton
New place to stay

To Valhalla II

MarkRating, 5 stars3 weeks ago
Nicole was communicative and friendly. The unit is one of three in the house, one of which belongs to Nicole. The entries are separate and the unit is private. It was quiet and easy. The place was clean and well put together. Sheets and bathroom were very clean. I enjoyed my stay.
Guest favorite
A spacious bedroom features a decorative brass bed with a floral bedspread. Soft lighting is provided by wall sconces, and a ceiling fan is mounted above. Large windows allow natural light to fill the room, while framed artwork adorns the walls.
Apartment in Oakland
4.9 out of 5 average rating, 63 reviews

Private Unit on Peaceful Farm, Convenient to Lake

JeromeRating, 5 stars9 months ago
All aspects of my stay were great. It was obvious time has been taken to ensure the suite was well furnished, clean and guests experience a home-away-from-home vibe. I definitely recommend this property if staying in the Deep Creek, MD area.

Apartment rentals with a hot tub

Top guest favorite
A warm wood fireplace stands as a focal point, complemented by a mounted TV above it. Shelves built into the wall display curated items, while the room features hardwood flooring and a doorway leading outside.
Apartment in Oakland
4.91 out of 5 average rating, 120 reviews

Private Unit on Farm with Kitchen & Balcony

KeeshaRating, 5 stars6 months ago
Our stay on the farm was peaceful and quiet. The view was amazing. The suite was clean and private. Kam was super responsive to an issue we had with the jacuzzi tub and was there within 15 minutes along with her maintenance man. Definitely recommended Haley Farm if you desire peace and that down on the farm feel!
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

LaurenRating, 5 stars42 months ago
An absolutely beautiful location! I was able to watch the leaves change in fall while soaking in the deck hot tub. The studio apartment was perfect as my home away from home while on a travel nursing assignment. I had everything I needed. I was able to bring my roku and watch my TV shows while relaxing in the recliner chair. The shower is very roomy. I love that a washer and dryer was included. The only thing I wish it had was a toaster oven…but that is a luxury not a need. The stove, toaster, and microwave were perfect for my month stay. I highly recommend this place for anyone looking to “get away” or working in nearby by Oakland, MD. The host is wonderful and very responsive.
Top guest favorite
A well-appointed kitchen features warm wood cabinetry and a spacious granite countertop. Stainless steel appliances, including a gas range and microwave, are visible. A central island provides additional preparation space, with overhead lighting illuminating the area. Natural light enters from the adjacent room.
Apartment in Grantsville
4.97 out of 5 average rating, 119 reviews

Yoder School Guest House with wifi and hot tub

MeaghanRating, 5 stars1 week ago
Rhoda’s listing was absolutely perfect! Very relaxing surroundings, private, and serene! The amenities were super helpful, too! Definitely recommend stopping by here!

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