Oakland Vacation Rentals from $306: Search Short-Term Rentals

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Our top choices for Oakland vacation 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.

$210 nightly

Nov 5 - Nov 6

Total with taxes and fees

A living room with a dark blue sofa, a tan armchair, a glass coffee table, and a patterned rug. There is a kitchen visible in the background with wooden cabinets and a microwave.

2. Lovely 2-bedroom basement apartment in t Oakland Md perfect for your stay

Oakland

$261 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

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

Oakland

Angela

$260 nightly

Oct 31 - Nov 1

Total with taxes and fees

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

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

Oakland

Abby H.

$635 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

5. Suites at Silver Tree: A118 Studio Standard View

Oakland

Mark

$237 nightly

Oct 31 - Nov 1

Total with taxes and fees

A balcony with a table and chairs, overlooking a lake and a beach.

6. Will O' The Wisp: 203A Efficiency/One Bath

Oakland

Joe and Becky D.

$257 nightly

Oct 31 - Nov 1

Total with taxes and fees

7. Captain's Quarters Deep Creek Log Cabin Oasis

Oakland

Brendan P.

$365 nightly

Nov 4 - Nov 5

Total with taxes and fees

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

Oakland

Erin C.

$260 nightly

Nov 2 - Nov 3

Total with taxes and fees

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Top Oakland Hotel Reviews

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

10/10 Excellent

"It was very nice and quiet, we had a great time and the location is excellent"

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!"

Find out more about Oakland

Everything you need to know about Oakland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oakland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oakland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $306 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland vacation 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 vacation.

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.

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Frequently asked questions

Can I find vacation rentals in Oakland?

Yes, there are vacation rentals close to top points of interest in Oakland, or you can choose a more remote option if you'd like a relaxing place to 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's the top vacation rental that Oakland has to offer?

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,: This highly rated vacation home rental in Oakland offers a patio, a barbecue grill, 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 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 vacation rentals are there in Oakland?

With 465 Expedia vacation rentals, you're sure 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 vacation rental in Oakland like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Oakland. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for family gatherings.

Oakland Vacation Rentals

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Our top choices for Oakland vacation rentals

1. Deer Pass – Luxury Glamping Yurt Near Deep CreekMd

2. Lovely 2-bedroom basement apartment in t Oakland Md perfect for your stay

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

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

5. Suites at Silver Tree: A118 Studio Standard View

6. Will O' The Wisp: 203A Efficiency/One Bath

7. Captain's Quarters Deep Creek Log Cabin Oasis

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

9. Suites at Silver Tree: A124 Studio Standard View

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

11. That Special Place

12. Dar's Deep Creek Log Cabin Timber Hideaway

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

14. Suites at Silver Tree: A204 Studio Standard View

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

16. Log chalet w/ hot tub & BBQ grill

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

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

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

20. Suites at Silver Tree: A210 Studio Standard View

Find vacation rentals that suit your style

Top Oakland Hotel Reviews

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

Find out more about Oakland

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