Oakland Holiday Rentals from AU$411: Search Short-Term Rentals

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Our top choices for Oakland holiday rentals

A cabin with a deck and a fire pit in the foreground.

1. Deer Pass – Luxury Glamping Yurt Near Deep CreekMd

Oakland

Holly M.

includes taxes & fees

8 Nov - 9 Nov

A cozy cabin interior with leather recliners, a stone fireplace, and a wooden wall with cabin rules posted.

2. Captain's Quarters Deep Creek Log Cabin Oasis

Oakland

Brendan P.

includes taxes & fees

28 Oct - 29 Oct

A living room with a sofa, a fireplace, a stone wall, and a balcony with curtains.

3. Lake Views! HOT TUB! Walk to Lake Rentals, Coffee & Eats. Minutes to Everything!

Oakland

Abby H.

includes taxes & fees

16 Nov - 17 Nov

A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

4. Suites at Silver Tree: A118 Studio Standard View

Oakland

Mark

includes taxes & fees

3 Nov - 4 Nov

5. Suites at Silver Tree: A114 One Bedroom Standard View

Oakland

Cristian

includes taxes & fees

27 Oct - 28 Oct

A wooden deck with Adirondack chairs, a sign reading 'WELCOME TO OUR PORT,' and a forested background.

6. Charming 4BR Home - HOT TUB - Oakland

Oakland

Steven P.

includes taxes & fees

29 Oct - 30 Oct

A spacious living area with a stone fireplace, wooden beams, a staircase, and a view of a lake.

7. Suites at Silver Tree: A212 One Bedroom Standard View

Oakland

Erin C.

includes taxes & fees

25 Oct - 26 Oct

8. Will O' The Wisp: 105A Efficiency/One Bath

Oakland

Patrick B.

includes taxes & fees

25 Oct - 26 Oct

A log cabin interior with a wooden staircase, a living area with two sofas, a coffee table, and a dining area with a table and chairs.

9. The winter is coming !!!

Oakland

"For those that like indoor entertainment and relaxation, this place is for you. There is air hockey, a video game machine, hot tub and tv in every room. The hot tub and air hockey is in an enclosed room off the living room so no worry about chlorine smells in the home. The video game Pac-Man is in the loft. You can relax by the fireplace place in the super comfy couches or sit on the porch swing and watch the deer or ground hogs walking by in the side yard."

Shere

includes taxes & fees

26 Oct - 27 Oct

10. Suites at Silver Tree: A124 Studio Standard View

Oakland

Lisa G.

includes taxes & fees

27 Oct - 28 Oct

A two-story log cabin with a balcony, surrounded by trees and snow.

11. That Special Place

Oakland

Patti R.

includes taxes & fees

25 Oct - 26 Oct

12. Will O' The Wisp: 302B One Bedroom/One Bath

Oakland

Cheryl W.

includes taxes & fees

26 Oct - 27 Oct

13. Will O' The Wisp: 107B One Bedroom/One Bath

Mountainside

Stacy S.

includes taxes & fees

26 Oct - 27 Oct

14. Dar's Deep Creek Log Cabin Timber Hideaway

Oakland

includes taxes & fees

8 Nov - 9 Nov

A spacious living room with a large sectional sofa, a round coffee table with a plant, and a sliding glass door leading to a deck.

15. Swings, Lakeview A-frame + Hot Tub, 120” screen

Oakland

Tyrone C.

includes taxes & fees

26 Oct - 27 Oct

A spacious cabin with a large living area, wooden floors, and a kitchen with stone accents.

16. Log chalet w/ hot tub & BBQ grill

Oakland

Jennifer M.

includes taxes & fees

25 Oct - 26 Oct

17. Suites at Silver Tree: A218 One Bedroom Standard View

Oakland

Ann Mahling

includes taxes & fees

1 Nov - 2 Nov

18. Suites at Silver Tree: A210 Studio Standard View

Oakland

Darlene

includes taxes & fees

26 Oct - 27 Oct

19. Suites at Silver Tree: A115 One Bedroom Lake View

Oakland

Angela

includes taxes & fees

8 Nov - 9 Nov

A log cabin interior with a fireplace, wooden walls, a sofa, a coffee table, and a dining area.

20. Luxury Deep Creek Lake Cabin • Sauna • Hot Tub • Arcade • Fire Pit •Pet Friendly

Oakland

Alex M.

includes taxes & fees

18 Nov - 19 Nov

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Top Oakland Hotel Reviews

Baja Motel

8/10 Good

"Nice stay. Two story property with only stairs access."

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

10/10 Excellent

"We had a wonderful time during our stay! There were several nice touches like doggie supplies and materials for smores. We truly enjoyed the hot tub and beautiful scenery all around. The house was roomy and the beds were super comfortable. The only minor complaints would be the slight smell of cigarette smoke throughout the house and strange placement of the lighting and switches."

Charming Dog Friendly Cottage w/ Dock & Fire Pit

8/10 Good

"The Red Cottage was a nice place to stay on our four night vacation away with our dog. The house was clean and did not smell of pets at all. Our dog adjusted well to the change of scenery and being in the mountains with new smells. The house was clean and well-stocked with kitchen supplies. Even with the request to bring paper products, there was a bag left for us with a roll of paper towels, two rolls of toilet paper, and mini dish and laundry soap, which was a nice surprise. The sleep number bed was super comfortable and we slept amazingly well. The proximity to downtown McHenry and Oakland is perfect, with lots of places to stop and explore within a short distance of the house. This was the perfect time of year to visit with Autumn Glory in full swing at Deep Creek. Our only complaint is the highway noise at the edge of the property was too much and made it hard to sit outside to enjoy the view. We enjoyed the hot tub very much, yet the last night we were there, the hot tub temp dropped to 95 degrees and the bubble stopped working. Given everything was so well maintained, this is sure to be quickly repaired."

The Garrett Inn

8/10 Good

"When we arrived to the Garrett Inn, we were able to check in, and were given a key to the room, and told where to park (each room's number was plainly painted on the space for each room, however, due to the configuration of the parking lot vs the way the room's were situated, the parking spaces were off-set from the individual rooms, so when parked for the room assigned, the space was two spaces offset. The room was well appointed, two full beds, a bathroom with a pocket door, a small table with two chairs. There was a microwave and room size refrigerator in the corner of the room, with coffee fixings and a coffee pot. The beds were firm but slept good. However, there was a bit of car noise from the busy highway (Rt 219), but it calmed down after about 11 pm. There was a great restaurant across the street, and also about a quarter of a mile down the road from the motel, both served great food. This motel was perfect for those who were exploring the local area and require a base to work from, this motel is perfect. It's not a chain motel, but it's quaint and fills all the basic needs of a motel."

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

10/10 Excellent

"Great, open property. Very clean. Fire pit was awesome! Lake access was perfect. Bill was amazing. If we needed anything, he was there in less than 5 minutes. We will definitely re-book!"

Lakefront/Dock/Amazing views HotTub

10/10 Excellent

"The guest house was absolutely beautiful. The space was exactly what we needed. We had room to gather and do things as a larger group but also had the space to be alone if we wanted to. The views are amazing, the house was clean, the bedrooms and bathrooms were wonderful as well. We thoroughly enjoyed our stay. I appreciated the quick response when I had questions both before and during our stay. I would absolutely recommend this property to anyone and would also stay again!"

The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

10/10 Excellent

"This place is exceptional! Very cozy, the beds are comfy, and that's including the sofa bed. Plenty of linens, towels and essentials. The fire pit was perfect, although we did not use the hot tub. Loved everything about this place, centrally located, it's clean and tidy, a lot of little extras, including vinyl records, a turntable, and games to play. We had a wonderful anniversary weekend getaway! Jeff is an ideal host. I HIGHLY recommend this place. Give it a try. You won't be disappointed!!"

Find out more about Oakland

Everything you need to know about Oakland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Oakland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakland. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland holiday rentals we have selected for you start as low as AU$411 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oakland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find holiday rentals in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Oakland. Make sure you have time to check out the ski areas and ecotours during your trip.

What are some of the best holiday rentals that Oakland has to offer?

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,: This highly rated holiday home rental in Oakland offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Some other top choices in Oakland are Lakefront/Dock/Amazing views HotTub and Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp.

How many holiday rentals are there in Oakland?

With 465 Expedia holiday rentals, you're guaranteed to find just the right place for your Oakland stay.

What’s there to see and do in Oakland?

Deep Creek Lake and Youghiogheny River are a couple of lovely local spots to get outside and enjoy nature. Herrington Manor State Park and Swallow Falls State Park are other places to visit while you're in town.

What’s a holiday rental in Oakland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakland. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.

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Check prices for these dates

Our top choices for Oakland holiday rentals

1. Deer Pass – Luxury Glamping Yurt Near Deep CreekMd

2. Captain's Quarters Deep Creek Log Cabin Oasis

3. Lake Views! HOT TUB! Walk to Lake Rentals, Coffee & Eats. Minutes to Everything!

4. Suites at Silver Tree: A118 Studio Standard View

5. Suites at Silver Tree: A114 One Bedroom Standard View

6. Charming 4BR Home - HOT TUB - Oakland

7. Suites at Silver Tree: A212 One Bedroom Standard View

8. Will O' The Wisp: 105A Efficiency/One Bath

9. The winter is coming !!!

10. Suites at Silver Tree: A124 Studio Standard View

11. That Special Place

12. Will O' The Wisp: 302B One Bedroom/One Bath

13. Will O' The Wisp: 107B One Bedroom/One Bath

14. Dar's Deep Creek Log Cabin Timber Hideaway

15. Swings, Lakeview A-frame + Hot Tub, 120” screen

16. Log chalet w/ hot tub & BBQ grill

17. Suites at Silver Tree: A218 One Bedroom Standard View

18. Suites at Silver Tree: A210 Studio Standard View

19. Suites at Silver Tree: A115 One Bedroom Lake View

20. Luxury Deep Creek Lake Cabin • Sauna • Hot Tub • Arcade • Fire Pit •Pet Friendly

Find holiday rentals that suit your style

Top Oakland Hotel Reviews

Baja Motel

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

Charming Dog Friendly Cottage w/ Dock & Fire Pit

The Garrett Inn

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Lakefront/Dock/Amazing views HotTub

HotTub-FirePit-8MintoWisp-Arcade-4BD-NoCleaningFee

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

Find out more about Oakland

Frequently asked questions

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