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

Oakland Vacation Rentals

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Oakland vacation rentals

A living room with a dark blue sofa, a tan armchair, a glass coffee table, and a patterned rug. There is a kitchen visible in the background with wooden cabinets and a microwave.

1. 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
$270 nightly
The price is $305
Oct 27 - Oct 28
Total with taxes and fees
Lovely 2-bedroom basement apartment in t Oakland Md perfect for your stay
A cabin with a deck and a fire pit in the foreground.

2. 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.
$220 nightly
The price is $249
Nov 9 - Nov 10
Total with taxes and fees
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
A spacious living area with a stone fireplace, wooden beams, a staircase, and a view of a lake.

3. 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
$265 nightly
The price is $299
Nov 5 - Nov 6
Total with taxes and fees
Suites at Silver Tree: A115 One Bedroom Lake View
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

4. Suites at Silver Tree: A118 Studio Standard View

Suites at Silver Tree: A118 Studio Standard View
Oakland
10.0 out of 10, Exceptional, (10 reviews)
"The hospitality was great."
United States
Mark
$234 nightly
The price is $265
Nov 5 - Nov 6
Total with taxes and fees
Suites at Silver Tree: A118 Studio Standard View
Interior

5. 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.
$332 nightly
The price is $347
Oct 28 - Oct 29
Total with taxes and fees
Captain's Quarters Deep Creek Log Cabin Oasis
A spacious living area with a stone fireplace, wooden beams, a staircase, and a view of a lake.

6. 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.
$256 nightly
The price is $289
Nov 5 - Nov 6
Total with taxes and fees
Suites at Silver Tree: A212 One Bedroom Standard View
Exterior

7. 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.
$245 nightly
The price is $277
Oct 27 - Oct 28
Total with taxes and fees
Will O' The Wisp: 206A Efficiency/One Bath
A two-story log cabin with a balcony, surrounded by trees and snow.

8. 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.
$374 nightly
The price is $397
Oct 27 - Oct 28
Total with taxes and fees
That Special Place
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, (71 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
$416 nightly
The price is $441
Oct 27 - Oct 28
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.

10. 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.
$236 nightly
The price is $267
Nov 5 - Nov 6
Total with taxes and fees
Suites at Silver Tree: A124 Studio Standard View
A balcony with two chairs, a view of a lake, and a dock with boats.

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.
$261 nightly
The price is $295
Oct 27 - Oct 28
Total with taxes and fees
Will O' The Wisp: 302B One Bedroom/One Bath
Exterior

12. 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.
$277 nightly
The price is $313
Oct 27 - Oct 28
Total with taxes and fees
Will O' The Wisp: 107B One Bedroom/One Bath
Outdoor dining

13. Dar's Deep Creek Log Cabin Timber Hideaway

Dar's Deep Creek Log Cabin Timber Hideaway
Oakland
$524 nightly
The price is $560
Nov 8 - Nov 9
Total with taxes and fees
Dar's Deep Creek Log Cabin Timber Hideaway
A two-story house with a deck and outdoor seating area.

14. Everwoods @ Deep Creek Lake - Speakeasy, hot tub, bunk room on private acreage

Everwoods @ Deep Creek Lake - Speakeasy, hot tub, bunk room on private acreage
Oakland
$652 nightly
The price is $739
Nov 1 - Nov 2
Total with taxes and fees
Everwoods @ Deep Creek Lake - Speakeasy, hot tub, bunk room on private acreage
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

15. 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
$246 nightly
The price is $279
Nov 5 - Nov 6
Total with taxes and fees
Suites at Silver Tree: A114 One Bedroom Standard View
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

16. 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
$236 nightly
The price is $267
Oct 28 - Oct 29
Total with taxes and fees
Suites at Silver Tree: A210 Studio Standard View
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

17. 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
$256 nightly
The price is $289
Nov 5 - Nov 6
Total with taxes and fees
Suites at Silver Tree: A218 One Bedroom Standard View
A spacious cabin with a large living area, wooden floors, and a kitchen with stone accents.

18. Log chalet w/ hot tub & BBQ grill

Log chalet w/ hot tub & BBQ grill
Oakland
9.0 out of 10, Wonderful, (4 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.
$777 nightly
The price is $858
Oct 27 - Oct 28
Total with taxes and fees
Log chalet w/ hot tub & BBQ grill
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.
$236 nightly
The price is $267
Nov 5 - Nov 6
Total with taxes and fees
Suites at Silver Tree: A204 Studio Standard 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.

20. 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.
$724 nightly
The price is $768
Nov 16 - Nov 17
Total with taxes and fees
Swings, Lakeview A-frame + Hot Tub, 120” screen
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

Will O' The Wisp: 103A Efficiency/One Bath

Will O' The Wisp: 103A Efficiency/One Bath

10/10 Excellent
"All the personnel at Wil o' the Wisp were exceedingly kind and pleasant! Our condo was charming and clean and the location was central to many activities. We ate at Ace's, the on-site restaurant, and had a delicious meal!"
David W. 2-night trip
Posted 1 hour ago
Will O' The Wisp: 103A Efficiency/One Bath

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 $288 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.