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Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Oakland vacation rentals

Property grounds

1. 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.
The price is ￥18,322
￥39,069 total
includes taxes & fees
Aug 18 - Aug 19
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
TV, fireplace

2. Rustic 3BR Cabin - HOT TUB - Oakland

Rustic 3BR Cabin - HOT TUB - Oakland
Paradise Point
Rustic 3BR Cabin - HOT TUB - Oakland
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.
The price is ￥26,925
￥47,117 total
includes taxes & fees
Aug 23 - Aug 24
Enjoyable 2-bedroom apartment in lovely Oakland near local hotspots
Interior

4. Charming 2BR Townhouse - FIREPLACE - Oakland

Charming 2BR Townhouse - FIREPLACE - Oakland
Oakland
9.6 out of 10, Exceptional, (9 reviews)
"Great place! Very comfortable living room and entertainment."
United States
Steve L.
The price is ￥13,056
￥55,883 total
includes taxes & fees
Aug 26 - Aug 27
Charming 2BR Townhouse - FIREPLACE - Oakland
Smart TV, fireplace, DVD player, books

5. The winter is coming !!!

The winter is coming !!!
Oakland
9.8 out of 10, Exceptional, (62 reviews)
"The host was very helpful. Nice quiet property in a good location."
United States
Brandi
The price is ￥22,799
￥63,348 total
includes taxes & fees
Aug 27 - Aug 28
The winter is coming !!!
Exterior

6. 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, (16 reviews)
"Great communication."
United States
William
The price is ￥36,644
￥119,360 total
includes taxes & fees
Sep 8 - Sep 9
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
Interior

7. 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
The price is ￥33,840
￥43,643 total
includes taxes & fees
Aug 26 - Aug 27
Suites at Silver Tree: A218 One Bedroom Standard View
Interior

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, (1 review)
"Would recommend!"
United States
Erin C.
The price is ￥33,840
￥43,812 total
includes taxes & fees
Aug 27 - Aug 28
Suites at Silver Tree: A212 One Bedroom Standard View
Interior

9. 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.
The price is ￥32,015
￥40,889 total
includes taxes & fees
Aug 26 - Aug 27
Suites at Silver Tree: A118 Studio Standard View
Exterior

10. 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.
The price is ￥35,704
￥77,027 total
includes taxes & fees
Aug 31 - Sep 1
That Special Place
Exterior

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

Will O' The Wisp: 105A Efficiency/One Bath
Oakland
9.6 out of 10, Exceptional, (24 reviews)
"would stay again!"
United States
Patrick B.
The price is ￥35,626
￥46,017 total
includes taxes & fees
Aug 27 - Aug 28
Will O' The Wisp: 105A Efficiency/One Bath
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
The price is ￥45,241
￥58,500 total
includes taxes & fees
Aug 18 - Aug 19
Will O' The Wisp: 508G Two Bedroom/One Bath
Interior

13. Suites at Silver Tree: A123 Studio Lake View

Suites at Silver Tree: A123 Studio Lake View
Oakland
The price is ￥36,303
￥46,958 total
includes taxes & fees
Aug 18 - Aug 19
Suites at Silver Tree: A123 Studio Lake View
TV, fireplace

14. 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.
The price is ￥59,363
￥125,917 total
includes taxes & fees
Aug 18 - Aug 19
Luxury Deep Creek Lake Cabin • Sauna • Hot Tub • Arcade • Fire Pit •Pet Friendly
TV, fireplace

15. 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.
The price is ￥47,919
￥116,283 total
includes taxes & fees
Aug 24 - Aug 25
Log chalet w/ hot tub & BBQ grill
Smart TV, foosball

16. 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.
The price is ￥64,859
￥141,200 total
includes taxes & fees
Sep 8 - Sep 9
Lakeview Chalet + Hot Tub, 120” screen
Smart TV, fireplace, video games, DVD player

17. Lake Views! HOT TUB! Walk to Lake Rentals, Coffee & Eats. Minutes to Everything!

Lake Views! HOT TUB! Walk to Lake Rentals, Coffee & Eats. Minutes to Everything!
Oakland
9.8 out of 10, Exceptional, (7 reviews)
"The place was so clean and fully stocked. We had a wonderful stay. Five stars!! "
United States
Lori S.
The price is ￥57,355
￥115,220 total
includes taxes & fees
Sep 7 - Sep 8
Lake Views! HOT TUB! Walk to Lake Rentals, Coffee & Eats. Minutes to Everything!
Interior

18. 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.
The price is ￥32,197
￥41,434 total
includes taxes & fees
Sep 13 - Sep 14
Suites at Silver Tree: A204 Studio Standard View
Flat-screen TV, fireplace, video games, DVD player

19. 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
The price is ￥36,119
￥46,749 total
includes taxes & fees
Aug 26 - Aug 27
Suites at Silver Tree: A115 One Bedroom Lake View
Interior

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
The price is ￥32,836
￥42,500 total
includes taxes & fees
Sep 7 - Sep 8
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.
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Top Oakland Hotel Reviews

Baja Motel

Baja Motel

10/10 Excellent
"Easy chexk i. And oit, friendly staff and nice rooms . Really good reataurant on site to boot"
Richard 2-night trip
Posted less than an hour ago
Baja Motel

Find out more about Oakland

Search for holiday rentals in Oakland on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakland using one of the methods below:

  • View our selection of featured holiday rentals in Oakland
  • Use the map to find apartments and other holiday homes in the Oakland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakland while they last

Look no further and take a look at our great range of rental properties in Oakland!

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.