Holiday houses in Oakland

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Top-rated holiday rentals in Oakland

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

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Top Guest favourite
The treehouse is elevated among bare branches, featuring a large deck with seating. Warm lighting highlights the wooden exterior, and expansive windows provide views of the surrounding forest. Steps lead down to the ground, enhancing accessibility to the natural setting.
Treehouse in McHenry
5 out of 5 average rating, 143 reviews

Bird's Eye View

Nestled high amidst the sturdy branches, "Bird's Eye View" is a sanctuary suspended between earth and sky. Located less than 5 minutes from Deep Creek Lake and perched among the foliage, our treehouse offers a panoramic perspective of the surrounding forest, granting its visitors an unparalleled vantage point to observe nature's wonders. Relax in the hot tub and take in an amazing sunset. The home is a harmonious blend of locally-crafted art and furniture to add rustic charm and modern comfort.

Guest favourite
A bright sleeping area features a spacious bed adorned with a patterned blue and white bedspread, complemented by yellow accent pillows. Natural light filters through two windows, which are framed by wooden trim. A wooden side table and a chair are positioned next to the bed.
Cabin in Oakland
4.99 out of 5 average rating, 163 reviews

Molly

Molly has a garage style window that opens up overlooking our creek at the point of 7 little waterfalls for your sleeping and hangout pleasure! A shared kitchen and bath completes the 3 small structures. Full bath plus an outdoor shower makes for great accommodations. We're within 5 miles from 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 - check other things to note about pets.

Top Guest favourite
A rustic cabin is nestled among trees, showcasing a gabled roof and large windows. The exterior is composed of wooden siding, blending with the autumn landscape. A small set of steps leads to the entrance, surrounded by fallen leaves and a natural, wooded setting.
Cabin in Friendsville
4.97 out of 5 average rating, 101 reviews

Fern Hill Cabin - rustic cabin near Deep Creek

Enjoy a comfortable rustic cabin with two bedrooms, one full bathroom, a powder room, spacious living room, kitchen and a dining area. Outside you can relax on a large screened porch or by the firepit under a blanket or stars. Some of the most beautiful areas such as Swallow Falls, Herrington Manor and Rock Maze are only a short drive away. Enjoy skiing at Wisp Resort or boating and swimming at Deep Creek State Park. Many wonderful restaurants and fun things to do are also a short drive away.

Guest favourite
A cozy living area features two comfortable sofas, adorned with festive pillows. A round ottoman sits in the center on a patterned rug. Wall shelves display decorative items, while natural light fills the space through multiple windows covered with sheer curtains.
Home in Swanton
4.96 out of 5 average rating, 108 reviews

The cozy cottage!

Hidden away in a serene natural atmosphere you will find our cozy cottage. This is an up to date, stylish and cozy cottage in North Glade on Oakway Rd. Perfect weekend retreat for a couple or a solo peaceful stay. The cottage has an open floor plan with all modern finishes. New furniture and modern appliances for your convenience. Stylish kitchen with open shelving, flat top stove with built in air fryer, farm sink, large under the counter fridge, microwave and keurig. No shared spaces.

Guest favourite
A spacious two-story home is set against a backdrop of greenery, showcasing a combination of stone and siding. A well-maintained lawn leads to a paved driveway, and large windows with decorative trim are visible along the facade, inviting natural light indoors.
Guest suite in Swanton
4.82 out of 5 average rating, 243 reviews

The View

Spacious, clean, modern basement efficiency apartment. Private entrance, private bath w/shower, private kitchenette with full size fridge & microwave (no stove), 1 queen size bed. Pool table, bar area and living room space with large TV equipped with satellite service. More space than a hotel room. View of Deep Creek Lake from front lawn in the distance, 11 Miles to Wisp, 6 miles to Deep Creek State Park and 1 mile to Thousand Acres Golf Course. NO Smoking, No Pets. We now have WIFI!!

Top Guest favourite
The tiny house features a wooden exterior, complemented by a sloped metal roof. A wooden deck with two chairs is positioned at the entrance, surrounded by greenery. Large windows allow natural light to fill the living space, offering a connection with the outdoors.
Cabin in Oakland
4.98 out of 5 average rating, 175 reviews

SUGARBUSH - Sweet Serenity Tiny House

Welcome to SUGARBUSH! "Suga" is a 450 sq. ft. custom built tiny house. She will comfortably accommodate 2 adults or a family with 2 small children. AGE REQUIREMENT to book this space is 25+. At this time we DO NOT allow pets. Suga sits on a 3+ acre lot that use to be used for cross country skiing. She got her name from two trails, Sugarbush Run and Sugarbush Shortcut that ran through the lot! We welcome you to stay and enjoy our wonderful little getaway here in Pleasant Valley.

Top Guest favourite
An outdoor seating area is surrounded by trees, featuring four dark chairs arranged around a circular firepit. The house in the background is light blue with a stone chimney and deck, offering a cozy woodland retreat.
Cabin in McHenry
4.98 out of 5 average rating, 110 reviews

1BR Romantic Couples Getaway!

Looking for a relaxing getaway with your significant other? We have you covered! Deep Creek Charm is nestled in the woods just a few minutes from Deep Creek Lake and all it has to offer! Enjoy the summer nights with the newly added outdoor firepit or soaking in the hot tub. For the colder evenings you can sit in by the cozy indoor fireplace and read a good book or watch tv on the large flat screen. You'll leave relaxed and ready to come back again in the future. Hope to see you soon!

Top Guest favourite
A wine bottle labeled 'Cherry Monmor' is positioned alongside a filled wine glass on a wooden table. The background features a panoramic view of a serene lake embraced by tree-covered hills displaying autumn foliage under a clear blue sky.
Home in Oakland
4.95 out of 5 average rating, 136 reviews

Lake View Loft Lodge on Deep Creek Lake

Seconds away from the lake, Trader's Coffee House, Brenda's Pizzeria, High Mountain Sports, and minutes away from Wisp Ski Resort, entertainment, shopping, food, and anything else you could want. Just eight miles south of Deep Creek Lake is historic Oakland, MD. Oakland is known for its small-town feel with local restaurants, small businesses, and popular festivals. Taking the time to visit Downtown Oakland is a must-see on your to-do list at Deep Creek Lake.

Top Guest favourite
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, 130 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.

Guest favourite
Two black rocking chairs are positioned on a stone patio, each adorned with a decorative pillow. A wide window provides views into the interior, framed by a white picket fence in the background, enhancing the outdoor sitting area.
Cottage in Oakland
4.96 out of 5 average rating, 162 reviews

Cheerful cottage 2 minutes from Deep Creek Lake

Just the right size and location for enjoying all Deep Creek Lake has to offer- including scenic hikes on many nearby trails, skiing at Wisp, or just enjoying time on the lake amongst bustling lake life. Then retreat back to our quaint cottage and enjoy time together. You will love our place because of its coziness, location, cleanliness, affordability and perfect size for a single family stay. *bathroom is in the bedroom *we have parking for a boat*

Superhost
A charming cottage is shown nestled in a snowy landscape. The exterior features wooden siding and two balconies that provide access to the home. Surrounding trees are visible, along with a clear blue sky overhead, creating a serene winter scene.
Cottage in Oakland
4.9 out of 5 average rating, 202 reviews

Pet friendly-Cottage in the Woods

Tucked conveniently between Swallow Falls State Park and Deep Creek Lake, this recently renovated 2 bd cottage has everything you need for a weekend getaway or a much needed week(s) long vacation!  Inside you will find a completely stocked kitchen, open living/dining area,  full size bathroom, 2 bedrooms and a cozy nook with sleeper sofa and desk.  Relax and unwind in the spacious backyard or charming balcony. *pets stay free

Guest favourite
A cozy sleeping area features a spacious bed covered in a textured teal quilt. Natural light floods the room through overhead skylights, highlighting the wooden ceiling beams. A round mirror and an accent lamp add functional elements to the inviting space.
Cabin in Davis
4.95 out of 5 average rating, 421 reviews

The Davis Loft - The Best Location in Davis!

The Davis Loft is the closest home rental to Blackwater Falls and is within walking distance to all that Davis has to offer. The loft has all the modern touches you would expect but still retains the right amount of rustic nostalgia that blends in so perfectly with the culture and landscape of the magnificent Canaan Valley. Have a front row seat to one of the most beautiful places in eastern North America.

Popular amenities for Oakland holiday rentals

Quick stats about holiday rentals in Oakland

  • Total holiday rentals

    Explore 10 holiday rentals in Oakland

  • Nightly prices starting at

    Oakland holiday rentals start at $105 NZD per night before taxes and fees

  • Verified guest reviews

    Over 750 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    10 of Oakland holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Oakland rentals

  • 4.8 Average rating

    Oakland stays are highly rated by guests—averaging 4.8 out of 5!

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