Oakland Holiday Rentals from AU$365: Search Short-Term Rentals

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Holiday Rentals in Oakland

"The house was beautiful and clean and in a great location (and smelled great too!). We arrived on Thanksgiving day and were pleasantly surprised to find a decorated Christmas tree lit by the fireplace. The house is a very convenient 10-15 minute drive to Oakland or McHenry. We loved sitting in the hot tub while it was snowing. Our granddaughter enjoyed the arcade game upstairs and was really excited about the bunk bed room. We had a wonderful stay and would love to come back in the warmer...

"A beautifully furnished cabin so close to the amenities and state parks of Deep Creek Lake. So well stocked with everything you need "

"Nice spot. A little loud with the highway and would have liked to have been able to use hottub but it didnt look clean. Otherwise great spot, super convenient for popping around the lake area."

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

"Thank you give us a great Thanksgiving."

"Great central location right off busy Garrett Highway. Nice amenities, could even suit 3 distinct groups with sleeping for 14. Walk out lower level directly to the lake, steps away. Nice hot tub, dock and kayaks. Fun game table and some arcade games if children come along. Enjoyable evening by the fire pit with s'mores! Easy to find, easy to book, responsive owners."

"The place had a perfect unobstructed view of the lake. The place was nice and warm for our winter trip. Comfortable furniture and bed for lounging around. The only complaint we had was when we arrived there was pee in the toilet and on the seat. The first thing we had to do was clean that ourselves not a fun start to the vacation. Overall though it was a good place and would recommend. "

"Our family enjoys DCL every other year for Thanksgiving. This year, we stayed at Magnolia and we were not disappointed. The house was well stocked with every-thing we needed. We loved the different sitting arrangements that afforded all of us a place to escape from the chaos, when necessary. "

"We had a fantastic time. The cabin was just as pictured. It was decorated so cute and had everything we needed for an enjoyable stay. We especially appreciated the fireplace as it was cold and snowing most of the time. The host was very attentive and responded to any questions very quickly. The area was so nice and the lake was beautiful. We will definitely be back and will definitely stay in the "Nirvana" cabin again. "

"Everything was just as described. Very clean and in a great location! Owner was so easy to work with. I would definitely book again! "

"Property was as listed. Great restaurants located on the property. Convenient location(driving distance) to get to Wisp resort or hiking trails. The walls were pretty thin, I could hear the conversation next door while trying to sleep one night. Upon arrival to the property we just noticed hair on the couch and remotes when we got there. Overall great place for cozy weekend."

includes taxes & fees

7 Jan - 8 Jan 2025

"Very clean. Great location and view of the lake. Loved having a fire pit and grill. Hosts were very communicative. Note that one of the bedrooms has a queen bed and the other one now has a bunk bed (twin on top, double on bottom). Would definitely stay here again!"

"Very clean and well maintained. Decor includes interesting items from around the world. Master bed was comfy, and owner was friendly on the phone. When she learned we were coming for my husband's birthday, she left a fun card for him with all the check-in info. We went in October and enjoyed the cozy gas fireplace and beautiful lake view. A busy road stands between the condo and the lake, but it's not a huge issue in cold weather when windows are closed. If you're looking for remote mountain...

"Enjoyed the house love you Can see the lake from "

"Cabin situated back in woods, beautiful grounds! Cabin Cottman’s very clean Swallow Falls was awesome. We really enjoyed the fire pit. all was great!!! "

"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 love the fire pit making s’mores with family and friends! Loved the hot tub! Very quiet wooded area, saw a black bear at the end of the property! We loved our stay! "

"My sister, daughter and I were in wow mode from the moment we walked in the door. The pictures on line did not do justice to the "Million Dollar View" description. The place was very clean, inviting, accommodating and beautiful! Appliances were very updated and snacks and treats were also left on the counter for us. Owner thought of everything to make this as pleasant as it was for us. We will definitely return again. Thank you"

"This was the second time we stayed at this house. We had beautiful weather, but the house was a wonderful retreat when we needed to cool down and relax. It's a quiet neighborhood that is located perfectly to get to town quickly or enjoy state parks."

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

"Great place and close to Wisp. Really enjoyed our stay! Will book there again. Great location with fire pit and yard! Just one small issue - there were dozens of lady bugs in the upstairs bedroom. It was fine but thought you all should know."

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Other types of properties in Oakland you may be interested in

"We’ve stayed here many times for quick trips. It’s always clean and a pleasant experience. Staff is friendly and helpful. "

includes taxes & fees

5 Jan - 6 Jan 2025

"A beautifully furnished cabin so close to the amenities and state parks of Deep Creek Lake. So well stocked with everything you need "

"Nice spot. A little loud with the highway and would have liked to have been able to use hottub but it didnt look clean. Otherwise great spot, super convenient for popping around the lake area."

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 AU$365 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.

Oakland Holiday Home Travel Info

Number of holiday homes	245
Popular accommodation	Oakland private holiday homes
Known landmarks	Herrington Manor State Park, Wolf Den Run State Park and Swallow Falls State Park
International airports	Washington, DC (IAD-Washington Dulles Intl.), Washington, DC (DCA-Ronald Reagan Washington National) and Morgantown, WV (MGW-Morgantown Municipal)

Recent reviews of Oakland properties

5/5 Excellent

"We’ve stayed here many times for quick trips. It’s always clean and a pleasant experience. Staff is friendly and helpful. "

A verified traveller stayed at The Garrett Inn

Posted 7 days ago

Amazing Central Location! Lakefront! Hot tub/dock!

5/5 Excellent

Great house we would stay here again

"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."

A verified traveller stayed at Amazing Central Location! Lakefront! Hot tub/dock!

Posted 11 days ago

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

5/5 Excellent

Thanksgiving at Deep Creek Lake

"The house was beautiful and clean and in a great location (and smelled great too!). We arrived on Thanksgiving day and were pleasantly surprised to find a decorated Christmas tree lit by the fireplace. The house is a very convenient 10-15 minute drive to Oakland or McHenry. We loved sitting in the hot tub while it was snowing. Our granddaughter enjoyed the arcade game upstairs and was really excited about the bunk bed room. We had a wonderful stay and would love to come back in the warmer months so we could enjoy the beautiful outdoor amenities, as well. The staff was very friendly and helpful with any questions we had. Would definitely recommend! "

A verified traveller stayed at Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Posted 3 weeks ago

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

5/5 Excellent

Family get together

"Everything was just as described. Very clean and in a great location! Owner was so easy to work with. I would definitely book again! "

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

Posted 3 weeks ago

Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village

5/5 Excellent

Cozy cabin

"We had a fantastic time. The cabin was just as pictured. It was decorated so cute and had everything we needed for an enjoyable stay. We especially appreciated the fireplace as it was cold and snowing most of the time. The host was very attentive and responded to any questions very quickly. The area was so nice and the lake was beautiful. We will definitely be back and will definitely stay in the "Nirvana" cabin again. "

A verified traveller stayed at Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village

Posted 3 weeks ago

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

5/5 Excellent

Thanksgiving away from home

"Our family enjoys DCL every other year for Thanksgiving. This year, we stayed at Magnolia and we were not disappointed. The house was well stocked with every-thing we needed. We loved the different sitting arrangements that afforded all of us a place to escape from the chaos, when necessary. "

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

Posted 3 weeks ago

Deep Creek Lake Townhome w/ Deck & Water Views

5/5 Excellent

Nice place

"Very clean and well maintained. Decor includes interesting items from around the world. Master bed was comfy, and owner was friendly on the phone. When she learned we were coming for my husband's birthday, she left a fun card for him with all the check-in info. We went in October and enjoyed the cozy gas fireplace and beautiful lake view. A busy road stands between the condo and the lake, but it's not a huge issue in cold weather when windows are closed. If you're looking for remote mountain solitude, this is not the place for you, but if you want a great view and don't mind the busy road, it's perfect."

A verified traveller stayed at Deep Creek Lake Townhome w/ Deck & Water Views

Posted 2 months ago

Private cabin with hot tub, outdoor dining, and fireplace

5/5 Excellent

Relaxing and enjoyable!

"Cabin situated back in woods, beautiful grounds! Cabin Cottman’s very clean Swallow Falls was awesome. We really enjoyed the fire pit. all was great!!! "

A verified traveller stayed at Private cabin with hot tub, outdoor dining, and fireplace

Posted 2 months 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?

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit: This highly rated holiday home rental in Oakland is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub. Some other top choices in Oakland are Modern house on the lake with private dock, hot tub, air hockey & central AC and Serene Mountain Escape: Hot Tub, Foosball, Views.

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?

Swallow Falls State Park and Deep Creek Lake are a couple of lovely local spots to get outside and enjoy nature. Herrington Manor State Park and Youghiogheny River 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

Plan, book, stay with confidence

Check Oakland holiday rental availability

Holiday Rentals in Oakland

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

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

Dog-friendly cabin with private hot tub, Ping-Pong & lake views

Dog-friendly cabin with private hot tub, Ping-Pong & lake views

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

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!

Lakefront/Dock/Amazing views HotTub

Lakefront/Dock/Amazing views HotTub

Bright condo with Deep Creek Lake views, wood fireplace

Bright condo with Deep Creek Lake views, wood fireplace

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

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

Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village

Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village

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,

Will O' The Wisp 203A: Lakefront Efficiency Condo, Access to Indoor Pool!

Will O' The Wisp 203A: Lakefront Efficiency Condo, Access to Indoor Pool!

Cozy, family-friendly, lakeview condo with gas grill & firepit

Cozy, family-friendly, lakeview condo with gas grill & firepit

Deep Creek Lake Townhome w/ Deck & Water Views

Deep Creek Lake Townhome w/ Deck & Water Views

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

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

Private cabin with hot tub, outdoor dining, and fireplace

Private cabin with hot tub, outdoor dining, and fireplace

Amazing Central Location! Lakefront! Hot tub/dock!

Amazing Central Location! Lakefront! Hot tub/dock!

New! Serenity Shores: Lake Area, Dogs OK, Hot Tub, Fireplace, Fire Pit, A/C!

New! Serenity Shores: Lake Area, Dogs OK, Hot Tub, Fireplace, Fire Pit, A/C!

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

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

Three Bedroom Cabin, Hot Tub, Wooded Lot, Access to Lake, Family, Pet Friendly.

Three Bedroom Cabin, Hot Tub, Wooded Lot, Access to Lake, Family, Pet Friendly.

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

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

Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough River

Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough River

Other types of properties in Oakland you may be interested in

The Garrett Inn

The Garrett Inn

Dog-friendly cabin with private hot tub, Ping-Pong & lake views

Dog-friendly cabin with private hot tub, Ping-Pong & lake views

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

Find out more about Oakland

Find out more about Oakland

Oakland Holiday Home Travel Info

Recent reviews of Oakland properties

Recent reviews of Oakland properties

The Garrett Inn

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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Frequently asked questions