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Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Oakland vacation rentals

Dining

1. 2BR - Forest Cabin - Fire Pit

2BR - Forest Cabin - Fire Pit
Oakland
10.0 out of 10, Exceptional, (1 review)
"An amazing getaway! Deep Creek is the best place to unwind. The house had everything we needed, and the scenery was stunning. Highly recommend for a peaceful vacation."
United States
Lakia J.
$419 nightly
The price is $474
Aug 13 - Aug 14
Total with taxes and fees
2BR - Forest Cabin - Fire Pit
Property grounds

2. Deer Pass – Luxury Glamping Yurt Near Deep CreekMd

Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
Oakland
10.0 out of 10, Exceptional, (10 reviews)
"Great getaway"
United States
Holly M.
$219 nightly
The price is $248
Aug 19 - Aug 20
Total with taxes and fees
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
Property grounds

3. 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.
$279 nightly
The price is $296
Aug 13 - Aug 14
Total with taxes and fees
Enjoyable 2-bedroom apartment in lovely Oakland near local hotspots
Exterior

4. New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
Oakland
10.0 out of 10, Exceptional, (15 reviews)
"Great communication."
United States
William
$670 nightly
The price is $757
Sep 8 - Sep 9
Total with taxes and fees
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
Interior

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, (1 review)
"Would recommend!"
United States
Erin C.
$243 nightly
The price is $275
Aug 16 - Aug 17
Total with taxes and fees
Suites at Silver Tree: A212 One Bedroom Standard View
Interior

6. 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, (5 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
$243 nightly
The price is $275
Aug 20 - Aug 21
Total with taxes and fees
Suites at Silver Tree: A218 One Bedroom Standard View
Smart TV, fireplace, DVD player, books

7. The winter is coming !!!

The winter is coming !!!
Oakland
9.8 out of 10, Exceptional, (61 reviews)
"The host was very helpful. Nice quiet property in a good location."
United States
Brandi
$375 nightly
The price is $398
Aug 27 - Aug 28
Total with taxes and fees
The winter is coming !!!
Interior

8. Suites at Silver Tree: A118 Studio Standard View

Suites at Silver Tree: A118 Studio Standard View
Oakland
10.0 out of 10, Exceptional, (6 reviews)
"Great accommodations, super easy to check in. Will be renting again. "
United States
Jason C.
$222 nightly
The price is $251
Aug 13 - Aug 14
Total with taxes and fees
Suites at Silver Tree: A118 Studio Standard View
Terrace/patio

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

Will O' The Wisp: 103A Efficiency/One Bath
Oakland
9.6 out of 10, Exceptional, (9 reviews)
"We had a wonderful time. The place was beautiful and close to everything. Enjoyed the hot tub too! "
United States
Molly C.
$253 nightly
The price is $286
Aug 16 - Aug 17
Total with taxes and fees
Will O' The Wisp: 103A Efficiency/One Bath
Interior

10. Suites at Silver Tree: A124 Studio Standard View

Suites at Silver Tree: A124 Studio Standard View
Oakland
6.0 out of 10, (1 review)
"The host was welcoming and for the most part the amenities were okay. The lobby of the hotel was absolutely beautiful. We had an initial issue with the fireplace, and the bathroom shower area was cold. The water would never get hot enough either. The television was in an awkward spot and the light from it interrupted our sleep. The refrigerator was too high up. We could not turn the tv optimally towards our bed. We loved Deep Creek Lake though, despite the weather it was still very beautiful,...
United States
Alvin H.
$231 nightly
The price is $261
Aug 13 - Aug 14
Total with taxes and fees
Suites at Silver Tree: A124 Studio Standard View
Exterior

11. That Special Place

That Special Place
Oakland
10.0 out of 10, Exceptional, (34 reviews)
"Fantastic property and couldn’t have asked for a better location for our quick family getaway/celebration! Plenty of space and privacy for everyone, and super convenient to local hot spots. Great communication with the host, and would definitely plan another stay!"
United States
Amy W.
$456 nightly
The price is $483
Aug 31 - Sep 1
Total with taxes and fees
That Special Place
Exterior

12. Will O' The Wisp: 508G Two Bedroom/One Bath

Will O' The Wisp: 508G Two Bedroom/One Bath
Mountainside
8.8 out of 10, Excellent, (3 reviews)
"The unit had everything we needed for a weekend getaway. Kitchen was well stocked and clean. Comfortable beds. Lots of handy hooks and cubbies. Nice view. Two restaurants on site were very good. Very close to state park, wisp resort, stores, and restaurants."
United States
Carol
$326 nightly
The price is $368
Aug 18 - Aug 19
Total with taxes and fees
Will O' The Wisp: 508G Two Bedroom/One Bath
TV, fireplace

13. 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.
$746 nightly
The price is $790
Sep 1 - Sep 2
Total with taxes and fees
Luxury Deep Creek Lake Cabin • Sauna • Hot Tub • Arcade • Fire Pit •Pet Friendly
TV, fireplace

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.
$663 nightly
The price is $730
Aug 30 - Aug 31
Total with taxes and fees
Log chalet w/ hot tub & BBQ grill
Smart TV, foosball

15. Lakeview Chalet + Hot Tub, 120” screen

Lakeview Chalet + 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.
$808 nightly
The price is $857
Sep 8 - Sep 9
Total with taxes and fees
Lakeview Chalet + Hot Tub, 120” screen
Interior

16. 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
Aug 13 - Aug 14
Total with taxes and fees
Suites at Silver Tree: A114 One Bedroom Standard View
Interior

17. Suites at Silver Tree: A210 Studio Standard View

Suites at Silver Tree: A210 Studio Standard View
Oakland
10.0 out of 10, Exceptional, (3 reviews)
"The property was absolutely beautiful! Right on the lake with amazing views! Secluded but close shops and restaurants! The room was very clean and welcoming! The only downside is the parking. When it’s dinner time, the hotel guests have to fight for parking spaces with the restaurant patrons. Other than that, we had an amazing stay. We’ll definitely be staying there again!"
United States
David H.
$232 nightly
The price is $262
Aug 16 - Aug 17
Total with taxes and fees
Suites at Silver Tree: A210 Studio Standard View
Interior

18. Suites at Silver Tree: A314 Studio & Loft Standard View

Suites at Silver Tree: A314 Studio & Loft Standard View
Oakland
9.6 out of 10, Exceptional, (13 reviews)
"great stay!"
United States
Mark M.
$264 nightly
The price is $299
Aug 13 - Aug 14
Total with taxes and fees
Suites at Silver Tree: A314 Studio & Loft Standard View
Interior

19. Suites at Silver Tree: A216 Studio Standard View

Suites at Silver Tree: A216 Studio Standard View
Oakland
9.0 out of 10, Wonderful, (2 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
Aug 16 - Aug 17
Total with taxes and fees
Suites at Silver Tree: A216 Studio Standard View
WiFi, bed sheets

20. Cozy Cabin, Sauna! Hot Tub! Filtered Lake Views!

Cozy Cabin, Sauna! Hot Tub! Filtered Lake Views!
Blakeslee
$657 nightly
The price is $708
Aug 31 - Sep 1
Total with taxes and fees
Cozy Cabin, Sauna! Hot Tub! Filtered Lake Views!
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 Deep Creek Hideaway w/ Fireplace

Dog Friendly Deep Creek Hideaway w/ Fireplace

8/10 Good
"The Grizzly Den is a very cute bear themed cabin with a superb location for summertime lake activities.It’s about a 5 minute drive from Deep Creek Lake, grocery stores, restaurants, etc. The cabin was clean, as were the linens and towels. The outdoor hot tub was nice. The bedspreads were a bit threadbare. My main critique would be that the cabin is very small and dark. It is rated to a maximum occupancy of 6 people, but we had two adults and two teens, and it was very cramped. I think 2-3 would be the maximum comfortable number."
Kristen G. 3-night trip
Posted 20 hours ago
Dog Friendly Deep Creek Hideaway w/ Fireplace

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 $286 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 Deep Creek Retreat | 5BR + Hot Tub + Game Room as a favorite home for rent in Oakland.

How many vacation rentals are there in Oakland?

With 473 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.