A sandy beach with a rocky shoreline, trees with autumn foliage, and a lake under a partly cloudy sky.

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Our top choices for Oakland holiday rentals

1. Deer Pass – Luxury Glamping Yurt Near Deep CreekMd

Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
Oakland
10.0 out of 10, Exceptional, (12 reviews)
"Great getaway"
United States
Holly M.
The price is £183
includes taxes & fees
2 Dec - 3 Dec
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd

2. Lovely 2-bedroom basement apartment in t Oakland Md perfect for your stay

Lovely 2-bedroom basement apartment in t Oakland Md perfect for your stay
Oakland
The price is £213
includes taxes & fees
18 Nov - 19 Nov
Lovely 2-bedroom basement apartment in t Oakland Md perfect for your stay

3. Suites at Silver Tree: A212 One Bedroom Standard View

Suites at Silver Tree: A212 One Bedroom Standard View
Oakland
10.0 out of 10, Exceptional, (2 reviews)
"Would recommend!"
United States
Erin C.
The price is £223
includes taxes & fees
13 Nov - 14 Nov
Suites at Silver Tree: A212 One Bedroom Standard View

4. Suites at Silver Tree: A210 Studio Standard View

Suites at Silver Tree: A210 Studio Standard View
Oakland
9.8 out of 10, Exceptional, (6 reviews)
"We loved everything about this property. The only thing I would make diferent is to have a breakfast menu available for your guest."
United States
Darlene
The price is £205
includes taxes & fees
14 Nov - 15 Nov
Suites at Silver Tree: A210 Studio Standard View

5. Woodland Cottage, Fire Pit & Park Pass

Woodland Cottage, Fire Pit & Park Pass
Oakland
10.0 out of 10, Exceptional, (43 reviews)
"Wonderful place, close to everything. Would definitely consider this home when we return to camp creek."
United States
Chander R.
The price is £279
includes taxes & fees
15 Nov - 16 Nov
Woodland Cottage, Fire Pit & Park Pass

6. Captain's Quarters Deep Creek Log Cabin Oasis

Captain's Quarters Deep Creek Log Cabin Oasis
Oakland
10.0 out of 10, Exceptional, (2 reviews)
"The cabin was clean and comfortable. Keith was very responsive to messages and incredibly helpful. We especially enjoyed the massage chairs and the hot tub Looking forward to visiting again.."
United States
Brendan P.
The price is £260
includes taxes & fees
16 Nov - 17 Nov
Captain's Quarters Deep Creek Log Cabin Oasis

7. Suites at Silver Tree: A118 Studio Standard View

Suites at Silver Tree: A118 Studio Standard View
Oakland
10.0 out of 10, Exceptional, (11 reviews)
"The hospitality was great."
United States
Mark
The price is £204
includes taxes & fees
15 Nov - 16 Nov
Suites at Silver Tree: A118 Studio Standard View

8. Dar's Deep Creek Log Cabin Timber Hideaway

Dar's Deep Creek Log Cabin Timber Hideaway
Oakland
The price is £335
includes taxes & fees
15 Nov - 16 Nov
Dar's Deep Creek Log Cabin Timber Hideaway

9. Winter is coming!!!

Winter is coming!!!
Oakland
9.8 out of 10, Exceptional, (73 reviews)
"We had a great stay!"
United States
Megan T.
The price is £319
includes taxes & fees
29 Nov - 30 Nov
Winter is coming!!!

10. Rustic 3BR Cabin - HOT TUB - Oakland

Rustic 3BR Cabin - HOT TUB - Oakland
Paradise Point
8.8 out of 10, Excellent, (3 reviews)
"House was clean, close to everything, quiet and cozy. Pool table was a plus hot tub is very small but that wasn’t an issue. Super nice peaceful and relaxing stay."
United States
Kayla B.
The price is £366
includes taxes & fees
28 Nov - 29 Nov
Rustic 3BR Cabin - HOT TUB - Oakland

11. That Special Place

That Special Place
Oakland
10.0 out of 10, Exceptional, (43 reviews)
"We were pleased with the accommodations. Thank you!"
United States
Patti R.
The price is £304
includes taxes & fees
22 Nov - 23 Nov
That Special Place

12. Pine Trees, Hot Tub & Game Room

Pine Trees, Hot Tub & Game Room
Oakland
10.0 out of 10, Exceptional, (49 reviews)
"My family loved the cabin! Perfect setting for a family weekend."
United States
Michael D.
The price is £378
includes taxes & fees
18 Nov - 19 Nov
Pine Trees, Hot Tub & Game Room

13. Will O' The Wisp: 206A Efficiency/One Bath

Will O' The Wisp: 206A Efficiency/One Bath
Oakland
9.2 out of 10, Wonderful, (17 reviews)
"Clean room, well equipped! Beautiful views and close to everything! "
United States
Erika M.
The price is £222
includes taxes & fees
18 Nov - 19 Nov
Will O' The Wisp: 206A Efficiency/One Bath

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

HotTub-FirePit-8MintoWisp-Arcade-4BD-NoCleaningFee
Oakland
10.0 out of 10, Exceptional, (48 reviews)
"This place had it all. Convenient located, Beautiful property inside and out. Host very receptive to our needs. Would go again for sure!"
United States
Steven (Bucky) W.
The price is £399
includes taxes & fees
15 Nov - 16 Nov
HotTub-FirePit-8MintoWisp-Arcade-4BD-NoCleaningFee

15. Suites at Silver Tree: A124 Studio Standard View

Suites at Silver Tree: A124 Studio Standard View
Oakland
8.0 out of 10, Very good, (2 reviews)
"The room was perfect!! No complaints here! Will definitely come back and stay"
United States
Lisa G.
The price is £205
includes taxes & fees
18 Nov - 19 Nov
Suites at Silver Tree: A124 Studio Standard View

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

Will O' The Wisp: 107B One Bedroom/One Bath
Mountainside
10.0 out of 10, Exceptional, (3 reviews)
"Great place to visit. Hope to come back next year"
United States
Stacy S.
The price is £237
includes taxes & fees
18 Nov - 19 Nov
Will O' The Wisp: 107B One Bedroom/One Bath

17. Will O' The Wisp: 302B One Bedroom/One Bath

Will O' The Wisp: 302B One Bedroom/One Bath
Oakland
10.0 out of 10, Exceptional, (1 review)
"Everything was very clean and comfortable."
United States
Cheryl W.
The price is £227
includes taxes & fees
18 Nov - 19 Nov
Will O' The Wisp: 302B One Bedroom/One Bath

18. Pine Loom Lodge | Dog-Friendly | Hot Tub + TV | Game Room | Near Ski, Lake &Golf

Pine Loom Lodge | Dog-Friendly | Hot Tub + TV | Game Room | Near Ski, Lake &Golf
Oakland
10.0 out of 10, Exceptional, (9 reviews)
"The lodge was very cozy and had everything we could need during our stay. The beds were very comfortable "
United States
Paula P.
The price is £536
includes taxes & fees
1 Dec - 2 Dec
Pine Loom Lodge | Dog-Friendly | Hot Tub + TV | Game Room | Near Ski, Lake &Golf

19. Lakefront, Level Yard, Hot Tub & Dock

Lakefront, Level Yard, Hot Tub & Dock
Paradise Point
9.8 out of 10, Exceptional, (127 reviews)
"Cozy comfortable & clean house , super convenient to Wisp, yet private and quiet. "
United States
Tricia S.
The price is £453
includes taxes & fees
18 Nov - 19 Nov
Lakefront, Level Yard, Hot Tub & Dock

20. Suites at Silver Tree: A218 One Bedroom Standard View

Suites at Silver Tree: A218 One Bedroom Standard View
Oakland
10.0 out of 10, Exceptional, (7 reviews)
"Our one bedroom suite was clean and comfortably appointed, The lobby was beautiful and a lovely place to congregate. Staff were friendly."
United States
Ann Mahling
The price is £223
includes taxes & fees
18 Nov - 19 Nov
Suites at Silver Tree: A218 One Bedroom Standard View
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oakland Hotel Reviews

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, apart-hotels, 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 favorite 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 depends 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 £204 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 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. 

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 Lakefront/Dock/Amazing views HotTub and Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp.

How many holiday rentals are there in Oakland?

With 465 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.