Oakland Vacation Rentals from CA $168: Short-Term Rentals for 2025

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Vacation Rentals in Oakland

"This was perfect for our family’s ski weekend at Wisp with our teens. We loved the hot tub, fireplace, and close proximity to restaurants. We’ll come back again!"

"This was my first time staying with VRBO. It was a million dollar view. There were just a few minor things that were mentioned before on other reviews that were not taken care of such as the hole in the master bedroom door, the smell of sewage in the kitchen the garbage disposal area, and also the stairs down to the dock area didn't seem too stable. I would have liked to have seen the fountain on but I do realize it's earlier in the year. The owners may want to change the curtains because not...

"Loved the location of this beautiful cabin - while the weather wasn’t always ideal for outdoor activities during our time in Deep Creek, we enjoyed spending time in the cabin!"

"Other than a hell of a lot of mosquitos being inside the home everything else was perfect after about an hour or 2 they were gone or maybe after a few drinks but I will be booking again the home was amazing"

"We had a great stay! Thank goodness for the dryer to dry our snow gear to keep us out on the slopes! The place awesome! And the host is great to work with and very responsive to needs!! Would love to come back again in the summer! Definitely recommend to anyone!"

CA $484 total

includes taxes & fees

Jul 30 - Jul 31

"The property was clean, comfortable and well stocked."

"This was our favorite of all the vacation rentals we have done. The cabin is charming and the amenities outstanding. The hot tub and firepit in the yard are great. We really enjoyed our stay"

"We had such a nice stay at the tiny house! The inside was adorable and the location is perfect. The views were beautiful and there were lots of hiking trails and delicious food nearby. We definitely plan to come back for another stay soon!"

"Host had great communication and was very friendly. Space was clean and welcoming. We loved the view, as well as how close it is to Wisp. We would stay again! "

Smart TV, fireplace, DVD player, table tennis

"Nice place for a weekend getaway"

"Communication was excellent (the most thorough welcome email I've ever received!)Very thoughtfully stocked (books, videos, marshmallows, etc)Lighting and decor created a very cozy ambianceClose to every place we wanted to go to (Wisp, Deep Creek State Park, Firewater, etc)"

"My family and I had a great time at the Red Cottage. We would definitely stay here again."

"The property was exactly as advertised and just what we wanted from our weekend!"

"Great family place. House is as described. User friendly appliances, tv’s and hot tub! All 14 of us enjoyed our stay."

2 bedrooms, iron/ironing board, WiFi, bed sheets

"I absolutely loved staying at the Love Shack! It was really cozy and cute. It’s dog friendly which was great! The hot tub was a great little add on to the property and the cabin is close to a lot of great places. We would definitely stay here again!"

"Property was wonderful. Location was great. Enjoyed our stay at this property. Thank you for letting us use your place."

"We had a great time, the location was great and the place was clean"

"Enjoyed our stay..location is great..close to restaurants and entertainment. "

"Nice place in the middle of deep creek. Short walk from lake, nice view."

"Property host never sent check in information nor did they answer any questions. The phone number listed was for someone who wasn’t even associated with the property so you couldn’t even talk anyone. Needless to say we weren’t able to actually stay there due to no communication from the host. Vrbo was useless in getting us a place to stay. Their guarantee turned out to be the biggest joke. They did nothing to find us a place to stay but we’re going to give us credit for future stays. So we were...

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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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland vacation rentals we have selected for you start as low as CA $168 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 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.

Recent reviews of Oakland properties

5/5 Excellent

"The restaurant next door was no longer open. We did find a lovely Italian restaurant just a mile or two down the road. Many places within a few minutes drive. "

A verified traveller stayed at Baja Motel

Posted 1 day ago

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

5/5 Excellent

"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. "

A verified traveller from Centreville, Maryland stayed at In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Posted 4 days ago

Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock Slip

5/5 Excellent

Multigenerational Family Vacation

"From the moment you enter the front door of this home the views of the lake are incredible which add to your overall peace and tranquility for your stay. This home is set up perfectly for large family gatherings There is plenty of room for everyone to have privacy with basically three master suites adding to the comfort of guests. A very short walk to boat slip is another plus. our group ranged in age from 10 to 75, everyone had a great time. David the host was very responsive to any issues. Can't say enough good things about this house"

A verified traveller stayed at Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock Slip

Posted 10 days ago

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

5/5 Excellent

Family Vaykay

"We had a wonderful vacation! The reservation and check-in process was extremely easy and streamlined! The property and home was beautiful and met all of our needs. Amenities were all inclusive! Outdoor hot tub and use of kayaks and paddleboards were awesome! We highly recommend this property! "

A verified traveller stayed at Lakefront, dog friendly, dock slip, hot tub, and fire pit

Posted 12 days ago

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

5/5 Excellent

Prefect Get away!!

"We had an amazing getaway at the Tiny House visiting from Washington, D.C. area for a couple of days. The property manager was easy to reach and made the check-in process seamless. When we first arrived, the place was a bit warm, likely due to the time of day, but it cooled down by the evening. The manager provided excellent recommendations for activities, including hiking, dining options, and a beach area for us and our dogs. We really enjoyed our stay and would definitely come back again!"

A verified traveller stayed at The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

Posted 3 weeks ago

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

5/5 Excellent

Great cabin by the lake

"It was perfect for our weekend stay. A lovely cabin on the hill with views of the lake and great lawn space for kids and pets. The space is clean and comes with linens, towels, and kitchen accessories, making it easy to have a quick or extended stay. "

A verified traveller stayed at Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Posted 3 weeks ago

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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?

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp: This highly rated vacation home rental in Oakland offers a fireplace, a selection of games, and a barbecue grill 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. You and your friends and family can relax into your vacation with amenities like a hot tub. Some other top choices in Oakland are Dog-friendly house on the lake, central AC, & EV charger and Modern house on the lake with private dock, hot tub, air hockey & central AC.

How many vacation rentals are there in Oakland?

With 561 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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Oakland Vacation Rentals

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Vacation Rentals in Oakland

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

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

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

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

EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

Modern house on the lake with private dock, hot tub, air hockey & central AC

Modern house on the lake with private dock, hot tub, air hockey & central AC

Lake Loft at Deep Creek Lake

Lake Loft at Deep Creek Lake

Bright condo with Deep Creek Lake views, wood fireplace

Bright condo with Deep Creek Lake views, wood fireplace

Cabin in the Woods

Cabin in the Woods

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

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

Deep Creek Lake Townhome w/ Deck & Water Views

Deep Creek Lake Townhome w/ Deck & Water Views

New Construction! Modern Lakefront A-Frame with Hot Tub + Fire Pit

New Construction! Modern Lakefront A-Frame with Hot Tub + Fire Pit

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

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

Charming Dog Friendly Cottage w/ Dock & Fire Pit

Charming Dog Friendly Cottage w/ Dock & Fire Pit

Charming home with furnished deck & lake view - walking distance to shops

Charming home with furnished deck & lake view - walking distance to shops

Huge, Beautiful and Quiet Home with Amazing Amenities

Huge, Beautiful and Quiet Home with Amazing Amenities

The Love Shack-- The BEST Couples and Small Family Retreat at Deep Creek Lake!

The Love Shack-- The BEST Couples and Small Family Retreat at Deep Creek Lake!

Sisters Treehouse

Sisters Treehouse

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

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

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

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

Cozy Lake Area Townhome w/ Lake Views, A/C & Grill

Cozy Lake Area Townhome w/ Lake Views, A/C & Grill

A quiet little town

A quiet little town

Find out more about Oakland

Find out more about Oakland

Recent reviews of Oakland properties

Recent reviews of Oakland properties

Baja Motel

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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Frequently asked questions