Oakland Holiday Rentals from €206: Search Short-Term Rentals

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Holiday Rentals in Oakland

"Great location and perfect place for a quick baseball tournament stay. Near plenty of food places, things to do and very quiet. Owners are very responsive to any questions. "

"Perfect place for a large group in close proximity to all the amenities the Deep Creek Lake region has to offer. Would rent again in a heartbeat. "

"Wonderful location and a great space for a large group!"

"In town to celebrate daughter Graduating from college! Great house, beds so comfy!!! House had all we needed & views are amazing! "

"Was a very nice home to spend a weekend at"

"Peggy was wonderful and the hayloft was great! "

includes taxes & fees

14 Oct - 15 Oct

"We had a blast at this wooded oasis. Tons of space and cozy rooms for every guest. Would love to book again. "

"Plenty of space, great access to the lake."

"Overall, a decent house, but it abuts a main road."

"We stayed in the 6A condo last year and this one was even better. Omly complaint is that a lot of the plugs were loose and we couldn’t plug anything into them except a select few."

"We loved it! Property was private, cabin was exactly as pictured but even better! Americana Decor was an added touch for the 4th of July. Was super clean. We used fire pit each night and the hot tub. You could hear Swallow Falls We would definitely recommend and would go back! Our first Vrbo experience, we were pleased!"

"Great place! Highly recommend. "

"We love this place! Our big family has stayed here each summer for years now and it’s perfect. Great location, beautiful house, helpful owner!"

includes taxes & fees

14 Oct - 15 Oct

"So many nice amenities to be comfortable for a week at a cabin in the woods, air conditioning and wifi. Many nearby trails and the private community property for nature appreciation activities."

"Beautiful home. Owner provided a lot of amenities."

"Location was great, close to lake and area amenities and a great value for location."

"We had a great stay. Everything was clean and very nice. Weather was rainy but still plenty of things to do inside. Great location and close to many activities indoors and outdoors. "

includes taxes & fees

3 Nov - 4 Nov

"It was everything and more then we could have anticipated. We would definitely rent again"

"We rented "

includes taxes & fees

29 Oct - 30 Oct

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Top Oakland Hotel Reviews

Charming Dog Friendly Cottage w/ Dock & Fire Pit

10/10 Excellent

"Excellent stay, we had a blast with the dogs. Just as advertised. The road was a little daunting to cross, but the picnic table down by the dock made it easy to stay down by the water for the day. Hot tub was great and everything in kitchen worked well (but BYO sugar & K Cups!)"

Bright condo with Deep Creek Lake views, wood fireplace

10/10 Excellent

"This was a very nice getaway. Home away from home. We were able to relax and enjoy each other without feeling like we were in someone else’s home. Shops were close by and the scenes were excellent. There was a problem with the toilet overflowing for the entire time. The TV in the downstairs bedroom didn’t work. We are pleased and will be coming back. We actually wanted to stay an extra night but it was already booked.Thank you for the opportunity to stay in your home. "

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

10/10 Excellent

"Cute tiny home with plenty of space in the kitchen and living room for two people. The house is very centrally located so it was no more than 15 mins to get anywhere we wanted to go. I particularly enjoyed the fire pit out back!"

Lakefront, dog friendly, dock slip, hot tub, and fire pit

10/10 Excellent

"Our stay at this vacation rental was truly unforgettable for our group of 12! The property is impeccably maintained and spotless. The thoughtful layout of both the home and outdoor spaces made it effortless for us to come together as a group or find quiet moments of relaxation on our own. Personally, I couldn’t get over how incredibly comfortable the beds and bedding were! The location is perfect: peaceful and scenic, while still being close to local attractions and amenities. We especially appreciated the hosts letting us know about the complimentary kayaks, paddleboards, and splash pads available at the dock—those little extras created cherished memories for our kids. This rental and responsiveness of the host went beyond all our expectations. We’re already looking forward to our next visit and wholeheartedly recommend it to anyone hoping to create lasting vacation memories. Thank you for making our getaway so special!"

Amazing Central Location! Lakefront! Hot tub/dock!

10/10 Excellent

"The stay was fabulous!! Having 2 dishwashers, 2 refrigerators 2stoves2coffeemakers! Brilliant!!We had plenty of space to cook for seventeen guests! The communal spaces were comfy and condusive for the games we played. We enjoyed the hot tub and the fire pit!"

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, apart-hotels, 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 favorite 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 depends 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 €206 per night. Entering your travel dates in the search wizard you might find 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 New: Lakefront Luxury Home with Private Indoor Heated Pool! and Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi.

How many holiday rentals are there in Oakland?

With 523 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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Holiday Rentals in Oakland

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Holiday Rentals in Oakland

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

New: Lakefront Luxury Home with Private Indoor Heated Pool!

Amazing Central Location! Lakefront! Hot tub/dock!

5BR lakefront retreat with hot tub, sauna, & dock

Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi

Couples Retreat: The HayLoft- Rustic Escape For 2

Luxury Log Chalet w/ Pool & Fireplace

Lakefront, dog friendly, dock slip, hot tub, and fire pit

Charming Dog Friendly Cottage w/ Dock & Fire Pit

Bright condo with Deep Creek Lake views, wood fireplace

Recreational Therapy- Private 2 Bedroom with Hot Tub and Firepit

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

Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock Slip

Private & Spacious 8-bedroom lodge with amazing outdoor space and game room

Dog-friendly secluded cabin with hot tub, firepit, lawn games, & great deck

Cabin in the Woods

Dog-friendly townhouse with wood-burning fireplace, balcony & washer/dryer

That Special Place

Best Location, lakefront, dockslip, family friendly, safe.

Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger!

Top Oakland Hotel Reviews

Charming Dog Friendly Cottage w/ Dock & Fire Pit

Baja Motel

The Garrett Inn

Bright condo with Deep Creek Lake views, wood fireplace

Cabin in the Woods

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

Lakefront, dog friendly, dock slip, hot tub, and fire pit

Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock Slip

Amazing Central Location! Lakefront! Hot tub/dock!

Find out more about Oakland

Frequently asked questions

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