A river flowing through a forest with a waterfall.

Search Holiday Rentals in Oakland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Oakland holiday rentals

A cabin with a deck and a fire pit in the foreground.

1. Deer Pass – Luxury Glamping Yurt Near Deep CreekMd

Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
Oakland
10.0 out of 10, Exceptional, (11 reviews)
"Great getaway"
United States
Holly M.
The price is £194
includes taxes & fees
5 Oct - 6 Oct
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
A wooden staircase leading to a covered porch with a view of the sky and clouds.

2. Enjoyable 2-bedroom apartment in lovely Oakland near local hotspots

Enjoyable 2-bedroom apartment in lovely Oakland near local hotspots
Oakland
9.0 out of 10, Wonderful, (2 reviews)
"The apartment is the main floor of an old home. It is located very close to downtown/historic Oakland. All the rooms are very spacious and minimalist aesthetic. It was a great base for our Garret County adventure. We were a party of 3. But a floor mattress makes it possible for a 4th. I only recommend bringing you own drinking water."
United States
Anne H.
The price is £228
includes taxes & fees
28 Sept - 29 Sept
Enjoyable 2-bedroom apartment in lovely Oakland near local hotspots
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

3. Suites at Silver Tree: A210 Studio Standard View

Suites at Silver Tree: A210 Studio Standard View
Oakland
9.6 out of 10, Exceptional, (5 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 £201
includes taxes & fees
30 Sept - 1 Oct
Suites at Silver Tree: A210 Studio Standard View
A log cabin interior with a wooden staircase, a living area with two sofas, a coffee table, and a dining area with a table and chairs.

4. The winter is coming !!!

The winter is coming !!!
Oakland
9.8 out of 10, Exceptional, (68 reviews)
"For those that like indoor entertainment and relaxation, this place is for you. There is air hockey, a video game machine, hot tub and tv in every room. The hot tub and air hockey is in an enclosed room off the living room so no worry about chlorine smells in the home. The video game Pac-Man is in the loft. You can relax by the fireplace place in the super comfy couches or sit on the porch swing and watch the deer or ground hogs walking by in the side yard."
United States
Shere
The price is £318
includes taxes & fees
28 Sept - 29 Sept
The winter is coming !!!
A spacious living area with a stone fireplace, wooden beams, a staircase, and a view of a lake.

5. 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 £212
includes taxes & fees
30 Sept - 1 Oct
Suites at Silver Tree: A212 One Bedroom Standard View
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

6. Suites at Silver Tree: A118 Studio Standard View

Suites at Silver Tree: A118 Studio Standard View
Oakland
10.0 out of 10, Exceptional, (8 reviews)
"The hospitality was great."
United States
Mark
The price is £200
includes taxes & fees
30 Sept - 1 Oct
Suites at Silver Tree: A118 Studio Standard View
A spacious living area with a stone fireplace, wooden beams, a staircase, and a view of a lake.

7. 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 £201
includes taxes & fees
29 Sept - 30 Sept
Suites at Silver Tree: A124 Studio Standard View

8. 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 £235
includes taxes & fees
28 Sept - 29 Sept
Will O' The Wisp: 107B One Bedroom/One Bath

9. Will O' The Wisp: 309B One Bedroom/One Bath

Will O' The Wisp: 309B One Bedroom/One Bath
Oakland
7.0 out of 10, Good, (2 reviews)
"Charming place. Kitchen (very small) is well appointed with necessary dishware and utensils. The amenities are great. The staff at the office were friendly and helpful. The attached Aces restaurant was outstanding, be prepared to take left overs to your condo. The rest could use a bit of a glow up. A few stubbed toes on the uneven flooring between the hall/bedroom and the living room and bathroom. The bedroom door to the hall did not close, the door may need shaved or adjusted. The...
United States
Pauline
The price is £247
includes taxes & fees
28 Sept - 29 Sept
Will O' The Wisp: 309B One Bedroom/One Bath
A wooden swing set overlooking a rustic house with a porch and a gravel driveway.

10. Charming 4BR Cabin - HOT TUB - Mountain View

Charming 4BR Cabin - HOT TUB - Mountain View
Oakland
The price is £494
includes taxes & fees
11 Oct - 12 Oct
Charming 4BR Cabin - HOT TUB - Mountain View
A balcony with a glass table and two chairs, overlooking a marina with boats and a lake.

11. 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 £229
includes taxes & fees
12 Oct - 13 Oct
Will O' The Wisp: 302B One Bedroom/One Bath
A spacious cabin with a large living area, wooden floors, and a kitchen with stone accents.

12. Log chalet w/ hot tub & BBQ grill

Log chalet w/ hot tub & BBQ grill
Oakland
9.4 out of 10, Exceptional, (3 reviews)
"Thank you SO MUCH for hosting us! The house was beautiful!! It was very convenient to everything we needed! We found the kitchen to be well stocked to cook in! The gameroom kept the kids very entertained, and the hot tub was well maintained and clean! Tony was great at communication and was very quick to reply! We would definitely stay here again!!!"
United States
Jennifer M.
The price is £558
includes taxes & fees
29 Sept - 30 Sept
Log chalet w/ hot tub & BBQ grill
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

13. 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, (6 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 £212
includes taxes & fees
29 Sept - 30 Sept
Suites at Silver Tree: A218 One Bedroom Standard View
A spacious living area with a stone fireplace, wooden beams, a staircase, and a view of a lake.

14. Suites at Silver Tree: A115 One Bedroom Lake View

Suites at Silver Tree: A115 One Bedroom Lake View
Oakland
10.0 out of 10, Exceptional, (1 review)
"Loved the location and Dutches Restaurant was top notch."
United States
Angela
The price is £226
includes taxes & fees
28 Sept - 29 Sept
Suites at Silver Tree: A115 One Bedroom Lake View
A spacious living room with a large sectional sofa, a round coffee table with a plant, and a sliding glass door leading to a deck.

15. Swings, Lakeview A-frame + Hot Tub, 120” screen

Swings, Lakeview A-frame + Hot Tub, 120” screen
Oakland
10.0 out of 10, Exceptional, (2 reviews)
"Place was very clean and tidy upon arrival! Would rent here again "
United States
Tyrone C.
The price is £589
includes taxes & fees
26 Oct - 27 Oct
Swings, Lakeview A-frame + Hot Tub, 120” screen
A log cabin interior with a fireplace, wooden walls, a sofa, a coffee table, and a dining area.

16. Luxury Deep Creek Lake Cabin • Sauna • Hot Tub • Arcade • Fire Pit •Pet Friendly

Luxury Deep Creek Lake Cabin • Sauna • Hot Tub • Arcade • Fire Pit •Pet Friendly
Oakland
10.0 out of 10, Exceptional, (4 reviews)
"Wonderful host!!"
United States
Alex M.
The price is £598
includes taxes & fees
8 Oct - 9 Oct
Luxury Deep Creek Lake Cabin • Sauna • Hot Tub • Arcade • Fire Pit •Pet Friendly
A spacious living area with a stone fireplace, wooden beams, a staircase, and a view of a lake.

17. Suites at Silver Tree: A216 Studio Standard View

Suites at Silver Tree: A216 Studio Standard View
Oakland
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful, quiet and CHILLLL getaway! The marina staff was READY and willing to help with anything. Location was great, lake was PERFECT"
United States
Joy S.
The price is £200
includes taxes & fees
1 Oct - 2 Oct
Suites at Silver Tree: A216 Studio Standard View
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

18. Suites at Silver Tree: A114 One Bedroom Standard View

Suites at Silver Tree: A114 One Bedroom Standard View
Oakland
10.0 out of 10, Exceptional, (1 review)
"Clean, friendly, beautiful."
United States
Cristian
The price is £206
includes taxes & fees
28 Sept - 29 Sept
Suites at Silver Tree: A114 One Bedroom Standard View
A spacious living area with a stone fireplace, wooden beams, a staircase, and a view of a lake.

19. Suites at Silver Tree: A204 Studio Standard View

Suites at Silver Tree: A204 Studio Standard View
Oakland
10.0 out of 10, Exceptional, (1 review)
"Clean room, nice property. Easy in and out. Great location."
United States
Leandra S.
The price is £201
includes taxes & fees
30 Sept - 1 Oct
Suites at Silver Tree: A204 Studio Standard View
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

20. Suites at Silver Tree: A318 One Bedroom & Loft Standard View

Suites at Silver Tree: A318 One Bedroom & Loft Standard View
Oakland
10.0 out of 10, Exceptional, (4 reviews)
"Wow this place is a gem! The amenities of a hotel with the privacy of a condo. Loved the lobby, outdoor spaces, dock, restaurant etc. We will be back !"
United States
Meagan D.
The price is £232
includes taxes & fees
28 Sept - 29 Sept
Suites at Silver Tree: A318 One Bedroom & Loft 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oakland Hotel Reviews

Baja Motel

Baja Motel

10/10 Excellent
"Super clean, friendly staff, well maintained. Quiet environment. Very relaxing"
Debra 2-night trip
Posted 13 hours ago
Baja Motel

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 £200 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.