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Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Oakland vacation 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.
$215 nightly
The price is $244
Oct 5 - Oct 6
Total with taxes and fees
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.
$264 nightly
The price is $280
Sep 30 - Oct 1
Total with taxes and fees
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
$223 nightly
The price is $253
Sep 30 - Oct 1
Total with taxes and fees
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, (70 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
$388 nightly
The price is $411
Sep 30 - Oct 1
Total with taxes and fees
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.
$233 nightly
The price is $265
Sep 30 - Oct 1
Total with taxes and fees
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
$222 nightly
The price is $251
Sep 30 - Oct 1
Total with taxes and fees
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.
$223 nightly
The price is $253
Oct 4 - Oct 5
Total with taxes and fees
Suites at Silver Tree: A124 Studio Standard View
Exterior

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.
$287 nightly
The price is $325
Oct 21 - Oct 22
Total with taxes and fees
Will O' The Wisp: 107B One Bedroom/One Bath
Exterior

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
$279 nightly
The price is $316
Oct 1 - Oct 2
Total with taxes and fees
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
$564 nightly
The price is $639
Oct 11 - Oct 12
Total with taxes and fees
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.
$251 nightly
The price is $285
Oct 12 - Oct 13
Total with taxes and fees
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.
$627 nightly
The price is $692
Sep 30 - Oct 1
Total with taxes and fees
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
$233 nightly
The price is $265
Sep 30 - Oct 1
Total with taxes and fees
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
$248 nightly
The price is $281
Sep 30 - Oct 1
Total with taxes and fees
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.
$706 nightly
The price is $749
Oct 26 - Oct 27
Total with taxes and fees
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.
$669 nightly
The price is $759
Oct 8 - Oct 9
Total with taxes and fees
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.
$222 nightly
The price is $251
Oct 1 - Oct 2
Total with taxes and fees
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
$227 nightly
The price is $257
Sep 30 - Oct 1
Total with taxes and fees
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.
$223 nightly
The price is $253
Sep 30 - Oct 1
Total with taxes and fees
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.
$263 nightly
The price is $298
Sep 30 - Oct 1
Total with taxes and fees
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.
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Top Oakland Hotel Reviews

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

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

10/10 Excellent
"The owner couldn’t have done anything more to make our stay perfect."
Lanz K. 8-night trip
Posted 11 hours ago
HotTub-FirePit-8MintoWisp-Arcade-4BD-NoCleaningFee

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 $251 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. 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 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.