A river flowing through a forest with a waterfall.

Oakland Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Oakland vacation rentals

A wooden staircase leading to a covered porch with a view of the sky and clouds.

1. 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.
$278 nightly
The price is $295
Sep 11 - Sep 12
Total with taxes and fees
Enjoyable 2-bedroom apartment in lovely Oakland near local hotspots
A bedroom with a bed, a ceiling fan, wooden walls, a window, and a door.

2. Contemporary 2BR Cabin - HOT TUB & Fireplace - Oakland

Contemporary 2BR Cabin - HOT TUB & Fireplace - Oakland
Oakland
$361 nightly
The price is $407
Sep 24 - Sep 25
Total with taxes and fees
Contemporary 2BR Cabin - HOT TUB & Fireplace - Oakland
A cabin with a deck and a fire pit in the foreground.

3. 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.
$215 nightly
The price is $243
Sep 21 - Sep 22
Total with taxes and fees
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
A living room with a stone fireplace, a large flat-screen TV, a sofa, and a coffee table.

4. Rustic 3BR Cabin - HOT TUB - Oakland

Rustic 3BR Cabin - HOT TUB - Oakland
Paradise Point
10.0 out of 10, Exceptional, (1 review)
"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.
$419 nightly
The price is $474
Sep 13 - Sep 14
Total with taxes and fees
Rustic 3BR Cabin - HOT TUB - Oakland
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

5. Suites at Silver Tree: A118 Studio Standard View

Suites at Silver Tree: A118 Studio Standard View
Oakland
10.0 out of 10, Exceptional, (7 reviews)
"The hospitality was great."
United States
Mark
$219 nightly
The price is $248
Sep 16 - Sep 17
Total with taxes and fees
Suites at Silver Tree: A118 Studio Standard View
A wooden deck with Adirondack chairs, a sign reading 'WELCOME TO OUR PORT,' and a forested background.

6. Charming 4BR Home - HOT TUB - Oakland

Charming 4BR Home - HOT TUB - Oakland
Oakland
9.8 out of 10, Exceptional, (15 reviews)
"Property was great. The kids loved the layout outside. The fireplace was awesome. Great place to stay."
United States
Steven P.
$486 nightly
The price is $549
Sep 17 - Sep 18
Total with taxes and fees
Charming 4BR Home - HOT TUB - Oakland
A spacious living area with a stone fireplace, wooden beams, a staircase, and a dining area.

7. 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
$260 nightly
The price is $294
Sep 11 - Sep 12
Total with taxes and fees
Suites at Silver Tree: A115 One Bedroom Lake View
A spacious living area with a stone fireplace, wooden beams, a staircase, and a dining area.

8. 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.
$241 nightly
The price is $273
Sep 13 - Sep 14
Total with taxes and fees
Suites at Silver Tree: A212 One Bedroom 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.

9. The winter is coming !!!

The winter is coming !!!
Oakland
9.8 out of 10, Exceptional, (66 reviews)
"The host was very helpful. Nice quiet property in a good location."
United States
Brandi
$411 nightly
The price is $436
Sep 22 - Sep 23
Total with taxes and fees
The winter is coming !!!

10. Will O' The Wisp: 105A Efficiency/One Bath

Will O' The Wisp: 105A Efficiency/One Bath
Oakland
9.6 out of 10, Exceptional, (25 reviews)
"would stay again!"
United States
Patrick B.
$256 nightly
The price is $289
Sep 11 - Sep 12
Total with taxes and fees
Will O' The Wisp: 105A Efficiency/One Bath
A spacious living area with a stone fireplace, wooden beams, a staircase, and a dining area.

11. 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.
$231 nightly
The price is $261
Sep 14 - Sep 15
Total with taxes and fees
Suites at Silver Tree: A124 Studio Standard View
A balcony with a glass table and two chairs, overlooking a marina with boats and a lake.

12. 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.
$261 nightly
The price is $295
Sep 30 - Oct 1
Total with taxes and fees
Will O' The Wisp: 302B One Bedroom/One Bath

13. 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.
$276 nightly
The price is $312
Sep 28 - Sep 29
Total with taxes and fees
Will O' The Wisp: 107B One Bedroom/One Bath
A spacious cabin with a large living area, wooden floors, and a kitchen with stone accents.

14. Log chalet w/ hot tub & BBQ grill

Log chalet w/ hot tub & BBQ grill
Oakland
10.0 out of 10, Exceptional, (2 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.
$628 nightly
The price is $693
Sep 16 - Sep 17
Total with taxes and fees
Log chalet w/ hot tub & BBQ grill
A log cabin interior with a fireplace, wooden walls, a sofa, a coffee table, and a dining area.

15. 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.
$709 nightly
The price is $752
Sep 17 - Sep 18
Total with taxes and fees
Luxury Deep Creek Lake Cabin • Sauna • Hot Tub • Arcade • Fire Pit •Pet Friendly
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.

16. Pool access, Lakeview A-frame + Hot Tub, 120” screen

Pool access, 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.
$736 nightly
The price is $780
Sep 22 - Sep 23
Total with taxes and fees
Pool access, Lakeview A-frame + Hot Tub, 120” screen
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

17. 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
$220 nightly
The price is $250
Sep 16 - Sep 17
Total with taxes and fees
Suites at Silver Tree: A210 Studio Standard View
A wooden dock leading to a lake with boats docked, surrounded by trees and grassy areas.

18. Welcome to Lakeski Lodge! Lake and Mountain View! Lake access and dock!

Welcome to Lakeski Lodge! Lake and Mountain View! Lake access and dock!
Oakland
4.8 out of 10, (3 reviews)
"We stayed at this lakeside home during the winter, and it was a cozy and memorable getaway. The snowy setting made the views especially beautiful, and the lake looked peaceful and picturesque surrounded by fresh snow. Once inside, the house felt warm, comfortable, and welcoming—perfect for escaping the cold.The home was clean and well laid out, with comfortable beds and a kitchen that had almost everything we needed. It was a great place to relax, unwind, and enjoy time together while staying...
United States
Kelly S.
$475 nightly
The price is $503
Sep 14 - Sep 15
Total with taxes and fees
Welcome to Lakeski Lodge! Lake and Mountain View! Lake access and dock!
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

19. Suites at Silver Tree: A209 Studio Lake View

Suites at Silver Tree: A209 Studio Lake View
Oakland
$257 nightly
The price is $290
Sep 13 - Sep 14
Total with taxes and fees
Suites at Silver Tree: A209 Studio Lake View
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

20. 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
$234 nightly
The price is $265
Sep 13 - Sep 14
Total with taxes and fees
Suites at Silver Tree: A114 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.
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
"I was very happy with the cleanliness and the amenities. The motel had lots of updated features. We were very happy with our stay."
Connie 1-night trip
Posted 2 days ago
Baja Motel

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Oakland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $248 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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?

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,: This highly rated vacation home rental in Oakland offers a patio, a barbecue grill, 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 you can cook with friends or family. Our travelers also rate Lakefront/Dock/Amazing views HotTub as a favorite home for rent in Oakland.

How many vacation rentals are there in Oakland?

With 465 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.