Oakland Vacation Rentals : Search Short-Term Rentals

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In two weeks

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Our top choices for Oakland vacation rentals

Abrams Creek Center

Elk Garden

Bill

$82 nightly

Apr 23 - Apr 24

Total with taxes and fees

Parsons Semper Fi Cabin w/ Fire Pit!

Parsons

$211 nightly

Apr 27 - Apr 28

Total with taxes and fees

House, 3 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, electric kettle

Modern Mountain Retreat Near Dolly Sods & Skiing 3 Bedroom Home

Timberline

$476 nightly

May 3 - May 4

Total with taxes and fees

Cozy Anchors Away Cabin Hideaway w/ Fire Pit!

Parsons

Jack

$211 nightly

Apr 24 - Apr 25

Total with taxes and fees

Parsons Cabin w/ Fire Pit & River Access!

Parsons

$211 nightly

Apr 24 - Apr 25

Total with taxes and fees

The Lodge at Wisp Resort

McHenry

Anonymous traveler

$237 nightly

Apr 24 - Apr 25

Total with taxes and fees

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Top Oakland Hotel Reviews

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!"

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!"

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

6/10 Okay

"This place met all of our needs and we had a very nice weekend away. However, there were several things that could be addressed. It was only me and my husband, not sure there was really room for anyone else. It is quite a small condo. We aren't terribly picky and I'm not complaining, just giving a review for others to base a decision. The 2nd story bed mattress was in very poor condition. We planned on sleeping there, as that was the only room with air conditioning. My husband described it perfectly it was like sleeping in a canoe, and one side was sleeping in a canoe with a board under you. We had to move to the first floor bed to have any sort of comfort, this bed was fine. Also the condo is very dated and could use some updated kitchen utensils. We made do with what was there, so not terrible but definitely not as comfortable as home. The location was great and the host was very responsive, but this rental could definitely use some TLC.....and please please replace the 2nd floor mattress. "

Level lakefront, family-friendly, hot tub, low fees, private dock

10/10 Excellent

"This house definitely suited our needs! It was just enough space for our two families. Rick, the owner was very responsive to our few questions. The view is amazing! The deck and fire pit were enjoyed by all. It was close to stores/restaurants. There were lots of extra's in the house - the host really thought of all the "What if's", they definitely went above and beyond. We will certainly be back. "

Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek

10/10 Excellent

"This cozy cottage was filled with many details missing from other cabins we’ve rented. Art, vignettes and lots of lighting options! We also loved the outdoor area filled with boulders, lighting, bottom and fire pit. The owners also accommodated a request without extra charge. We also enjoyed the restaurants they recommended, Moonshadow where they have live music. We enjoyed exploring the area with the large Deep Creek lake sourrounded by mountains. "

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 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 Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp and Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip.

How many vacation rentals are there in Oakland?

With 473 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.

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Check prices for these dates

Our top choices for Oakland vacation rentals

Abrams Creek Center

Parsons Semper Fi Cabin w/ Fire Pit!

Modern Mountain Retreat Near Dolly Sods & Skiing 3 Bedroom Home

Cozy Anchors Away Cabin Hideaway w/ Fire Pit!

Parsons Cabin w/ Fire Pit & River Access!

The Lodge at Wisp Resort

Find vacation rentals that suit your style

Top Oakland Hotel Reviews

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

The Garrett Inn

Baja Motel

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

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

Lakefront/Dock/Amazing views HotTub

Level lakefront, family-friendly, hot tub, low fees, private dock

Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek

Find out more about Oakland

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