Oakland Holiday Rentals : Search Short-Term Rentals

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Holiday 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!"

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!"

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

"Location was great , house was just missing bed linens"

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

"I took the family of 6 to the lake. It was chilly outside but this property was perfect. Plenty of space for us all, each couple had a bathroom. The living room open concept with kitchen was perfect for us being able to enjoy the tv, games, food and beverages together. "

"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"

"The inside of the house was very clean and very tastefully decorated. The view was out of this world! The one thing that we would like to note, is that prior guests left large dog poop on the balcony that was not cleaned up by the staff. In addition, there was a bag of dog poop left in front of the home. Everything else was excellent and we still appreciate it being dog-friendly."

"We had a Wonderful stay in this Property.. enjoyed the view and the location was perfect.. very clean and comfortable"

"First time visiting Deep Creek and the Tiny House didnt dissapoint"

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

"Liked the old school cabin look"

"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! "

"Thoroughly enjoyed our stay. The home was super clean, the property was beautiful and location super since it was close to multiple state parks."

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

"Plenty of room for our large group and the house is in great condition. Checking in and out was simple, and the hosts were very responsive to questions before our stay."

"We enjoyed the gathering place and our time at Deep creek. This house was very nice."

"We were so impressed!!! So much fun and so relaxing."

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

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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, 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 favourite 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 depend 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 per night. Entering your travel dates in the search wizard might find you 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.

Recent reviews of Oakland properties

5/5 Excellent

Cute little place in the woods.

"The.house had everything thing we needed. The master bed was very comfortable and hot tub was amazing. The only problem we encountered was that as soon as we pulled up i realized i no longer had cell service so we had to go back to the main gate so we could pull up the code information. This was really our fault as i should have written it down ahead of time. Our whole reason for going was to rest which we definitely did. Very relaxing. "

A verified traveller stayed at Cabin in the Woods

Posted 3 days ago

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

5/5 Excellent

Just enough

"This is a great spot with a cool design aesthetic. It was just enough space for me, my husband and dog. So many places I’ve stayed have an abundance of “stuff” and things can be hard to find. The love shack had just enough of everything and it felt like an actual home. Place was super clean and the location is great. Communication was easy and straightforward"

A verified traveller from Alexandria, VA stayed at The Love Shack-- The BEST Couples and Small Family Retreat at Deep Creek Lake!

Posted 2 weeks ago

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

5/5 Excellent

Great stay!

"The property was great. Everything worked well. A rustic little place but with modern amenities. We had a great time! "

A verified traveller stayed at Dog-friendly secluded cabin with hot tub, firepit, lawn games, & great deck

Posted 3 weeks ago

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 Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp and Deep Creek Lake views from the elevated deck & deluxe suite - near golf.

How many holiday rentals are there in Oakland?

With 645 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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Oakland Holiday Rentals

Check prices for these dates

Holiday Rentals in Oakland

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

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

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

Wandering Woods- Dog-friendly 3 bedroom home with lake access and hot tub!

Bright condo with Deep Creek Lake views, wood fireplace

Deep Creek Lake views from the elevated deck & deluxe suite - near golf

Cabin in the Woods

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

EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

Will O' The Wisp 706H: Top Lakefront Panoramic View Condo, Sleeps 4, Free WIFI!

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

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

Dog-friendly Lakefront Log Home on a Quiet Cove with Front Deck & Private Dock

Deep Creek Lake Townhome w/ Deck & Water Views

Dog-friendly home near state parks with firepit, pool table, fireplace, & decks

Huge, Beautiful and Quiet Home with Amazing Amenities

Amazing Central Location! Lakefront! Hot tub/dock!

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

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

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

Find out more about Oakland

Recent reviews of Oakland properties

Cabin in the Woods

The Garrett Inn

Will O' The Wisp 706H: Top Lakefront Panoramic View Condo, Sleeps 4, Free WIFI!

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

Deep Creek Lake views from the elevated deck & deluxe suite - near golf

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

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

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Wandering Woods- 3 Bedroom Home with Hot Tub and Firepit

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