Oakland Vacation Rentals from $385: Search Short-Term Rentals

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Our top choices for Oakland vacation rentals

Deer Pass – Luxury Glamping Yurt Near Deep CreekMd

Oakland

Holly M.

$211 nightly

May 6 - May 7

Total with taxes and fees

In the heart of Deep Creek Lake! - "Shamrock Inn"

Mountainside

Michael M.

$441 nightly

May 6 - May 7

Total with taxes and fees

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

Mountainside

Stacy S.

$285 nightly

May 6 - May 7

Total with taxes and fees

“Moonbeam” (Airstream)

Oakland

Scott H.

$205 nightly

May 6 - May 7

Total with taxes and fees

Enjoyable 2-bedroom apartment in lovely Oakland near local hotspots

Oakland

$222 nightly

May 6 - May 7

Total with taxes and fees

Suites at Silver Tree: A118 Studio Standard View

Oakland

Anonymous traveler

$236 nightly

May 21 - May 22

Total with taxes and fees

Will O' The Wisp: 205A Efficiency/One Bath

Oakland

Raymond K.

$262 nightly

May 6 - May 7

Total with taxes and fees

Suites at Silver Tree: A210 Studio Standard View

Oakland

David H.

$237 nightly

May 25 - May 26

Total with taxes and fees

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Top Oakland Hotel Reviews

The Garrett Inn

10/10 Excellent

"We have stayed at the Garrett Inn numerous times over the past ten years. The staff/owners are always very courteous and the rooms are always clean. A very nice and quiet place to stay the night."

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

6/10 Okay

"Cute little place. Our only complaint was that the cleaning was not great. There was dog hair everywhere. I know it's pet friendly but it didn't even look like they ran the vacuum for a while. The owner was responsive and refunded the cleaning fee. I take a getaway to relax not to clean someone else's house."

Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip

10/10 Excellent

"A perfect getaway for family! We had so much fun at the lake- fishing and swimming. The hot tub was also very popular after time at the lake:) The house had ample space and was well stocked -lots of room to spread out! The kids loved the game room in the basement and the deck outside was a great place to sit and talk. We are definitely talking about coming back next year. Thank you to the hosts that reached out to see how our stay was going throughout the weekend!"

Sisters Treehouse

10/10 Excellent

"We enjoyed our stay it was a nice place to come back to winddown after a day of walking the parks, shopping, and sightseeing. Thank You.The Host was nice, and was quick to respond to emails with rental information, we needed to know for our stay at the beginning of April.The Kitchen was clean, well stocked with the essential kitchen equipment - dishes utensils, pots and pans to cook a stay-in meal.Fireplace was not working, but the Host did let us know that ahead of time in the rental information.Rooms were neat and tidy, pillows and blankets were provided by Host as well as some cleaning ,paper products, trash bags and toiletries. We needed to bring sheets and pillowcases, also towels for kitchen and bathrooms, and for swimming.We had a nice view of Deep Creek Lake from the back of the home, spacious deck off of livingroom and a lower level patio.We were located right off the main road that goes around the lake which was convenient to local restaurants, shopping, and sight seeing in the area. We were in close proximity to three State Parks-Deep Creek, Herrington Manor and Swallow Falls. "

EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

10/10 Excellent

"This is the best VRBO I have ever been to! Absolutely spotlessly clean, such a private and cozy feel. We spent 2 days here relaxing and just having a girls getaway and I have NO notes. A beautiful cabin, despite the cabin right next door we felt secluded. It was quiet, comfortable, and the perfect space for us. Communication with the owners is easy and they’re very kind and responsive. I will 100% be back!! "

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

10/10 Excellent

"Walking into the cabin and seeing the view from the living room was amazing! ... a beautiful sweeping view of a cow pasture on the hillside and a mountain ridge. Fireplace with provided firelogs and electric candles on the mantel made for a relaxing evening. Hot tub was great after a day of hiking. Little touches like the couch cover, ball and petwipes for dogs was nice. Carol even provided dog bowls and makings for s'mores! Rooms and bathrooms very clean with nice private views thru the woods. Watching a pileated woodpecker and a red-headed woodpecker while breakfasting was special. Would definitely stay there again, and I'd like to see the cabin in other seasons. Decks with rockers were nice, although the weather turned cold when we were there so I couldn't sit outside for long. Our family of 4 adults 1 dog stayed there April 5-8, 2026. Thanks, Carol, for sharing your cabin and answering our questions so promptly!"

Dog-friendly house on the lake, central AC, & EV charger

8/10 Good

"This property was well worth the money we paid for it. Breathtaking view of the Lake. For a lakefront property, all others don't compare! A few things need some attention such as, the upstairs fireplace does not come on and we had a few days of below freezing temperatures. Had to up the setting on the whole house furnace, which worked very well by warming up the house quickly. One of the downstairs showers (angle one) leaks pretty badly when using, and the shower head is very loose. For a dog-friendly house, there is essentially no yard to take our pet out to. And the driveway going down to the house is very tricky to navigate. But we had a good time in a very lovely and clean house with a well furnished kitchen. (The icemake doesn't spit out ice, just water). Would visit this house again in the future."

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 $385 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 Dog-friendly house on the lake, central AC, & EV charger and Lakefront/Dock/Amazing views HotTub.

How many vacation rentals are there in Oakland?

With 472 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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Check prices for these dates

Our top choices for Oakland vacation rentals

Deer Pass – Luxury Glamping Yurt Near Deep CreekMd

In the heart of Deep Creek Lake! - "Shamrock Inn"

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

“Moonbeam” (Airstream)

Enjoyable 2-bedroom apartment in lovely Oakland near local hotspots

Suites at Silver Tree: A118 Studio Standard View

Will O' The Wisp: 205A Efficiency/One Bath

Suites at Silver Tree: A210 Studio Standard View

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

Lakeview Chalet in Deep Creek Lake + Hot Tub

Suites at Silver Tree: A212 One Bedroom Standard View

Rustic cabin w/hot tub & game room near Wisp

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

Suites at Silver Tree: A123 Studio Lake View

Luxor Mountaintop Cabin-Castle at Deep Creek Lake

Suites at Silver Tree: A218 One Bedroom Standard View

Suites at Silver Tree: A216 Studio Standard View

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

Suites at Silver Tree: A314 Studio & Loft Standard View

Will O' The Wisp: 710H Studio Loft/One Bath

Find vacation rentals that suit your style

Top Oakland Hotel Reviews

The Garrett Inn

Find out more about Oakland

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