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

Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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, (12 reviews)
"Great getaway"
United States
Holly M.
$210 nightly
The price is $238
Dec 2 - Dec 3
Total with taxes and fees
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
A living room with a dark-colored sofa, a glass coffee table, a brown armchair, and a large mirror on the wall.

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
$248 nightly
The price is $282
Nov 11 - Nov 12
Total with taxes and fees
Lovely 2-bedroom basement apartment in t Oakland Md perfect for your stay
A spacious living area with a stone fireplace, wooden beams, a staircase, and a view of a lake.

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.
$258 nightly
The price is $292
Nov 14 - Nov 15
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.

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
$232 nightly
The price is $263
Nov 15 - Nov 16
Total with taxes and fees
Suites at Silver Tree: A210 Studio Standard View
A two-story house with a porch, a picnic table, and outdoor seating.

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.
$312 nightly
The price is $355
Nov 12 - Nov 13
Total with taxes and fees
Woodland Cottage, Fire Pit & Park Pass
A wooden cabin interior with a dining table, bar stools, a fireplace, and a kitchen area.

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.
$297 nightly
The price is $336
Nov 15 - Nov 16
Total with taxes and fees
Captain's Quarters Deep Creek Log Cabin Oasis
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

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
$236 nightly
The price is $267
Nov 11 - Nov 12
Total with taxes and fees
Suites at Silver Tree: A118 Studio Standard View
Outdoor dining

8. Dar's Deep Creek Log Cabin Timber Hideaway

Dar's Deep Creek Log Cabin Timber Hideaway
Oakland
$353 nightly
The price is $402
Nov 12 - Nov 13
Total with taxes and fees
Dar's Deep Creek Log Cabin Timber Hideaway
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. Winter is coming!!!

Winter is coming!!!
Oakland
9.8 out of 10, Exceptional, (73 reviews)
"We had a great stay!"
United States
Megan T.
$403 nightly
The price is $427
Nov 11 - Nov 12
Total with taxes and fees
Winter is coming!!!
A living room with a stone fireplace, a large flat-screen TV, a sofa, and a coffee table.

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.
$431 nightly
The price is $489
Nov 28 - Nov 29
Total with taxes and fees
Rustic 3BR Cabin - HOT TUB - Oakland
A two-story log cabin with a balcony, surrounded by trees and snow.

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.
$387 nightly
The price is $410
Nov 11 - Nov 12
Total with taxes and fees
That Special Place
A two-story house with a deck, large windows, and a chimney.

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.
$443 nightly
The price is $503
Nov 15 - Nov 16
Total with taxes and fees
Pine Trees, Hot Tub & Game Room
Pool

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.
$257 nightly
The price is $292
Nov 16 - Nov 17
Total with taxes and fees
Will O' The Wisp: 206A Efficiency/One Bath
A cozy cabin interior with a stone fireplace, leather furniture, and large windows offering a view of the outdoors.

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.
$502 nightly
The price is $527
Nov 15 - Nov 16
Total with taxes and fees
HotTub-FirePit-8MintoWisp-Arcade-4BD-NoCleaningFee
A spacious living area with a stone fireplace, wooden beams, a staircase, and a view of a lake.

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.
$237 nightly
The price is $269
Nov 11 - Nov 12
Total with taxes and fees
Suites at Silver Tree: A124 Studio Standard View
Pool

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.
$280 nightly
The price is $317
Nov 16 - Nov 17
Total with taxes and fees
Will O' The Wisp: 107B One Bedroom/One Bath
A balcony with two chairs, a view of a lake, and a dock with boats.

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.
$264 nightly
The price is $300
Nov 17 - Nov 18
Total with taxes and fees
Will O' The Wisp: 302B One Bedroom/One Bath
A cabin with a covered deck, outdoor seating, and a fire pit.

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.
$624 nightly
The price is $707
Nov 30 - Dec 1
Total with taxes and fees
Pine Loom Lodge | Dog-Friendly | Hot Tub + TV | Game Room | Near Ski, Lake &Golf
A deck with a view of a lake, surrounded by trees and a grassy area with chairs.

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.
$531 nightly
The price is $601
Nov 15 - Nov 16
Total with taxes and fees
Lakefront, Level Yard, Hot Tub & Dock
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

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
$241 nightly
The price is $274
Nov 11 - Nov 12
Total with taxes and fees
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

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

10/10 Excellent
"The house was very cute and private. Had everything you needed and plenty of space for the four ladies in our group. The hot tub was very nice even with the temperature in the 30s. We would love to stay again!"
Claire S. 2-night trip
Posted 2 days ago
Dog Friendly Cabin in the Woods, Hot Tub & Firepit

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 $267 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.