Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Oakland vacation rentals

Smart TV, fireplace, video-game console, DVD player

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

HotTub-FirePit-8MintoWisp-Arcade-4BD-NoCleaningFee
Oakland
10.0 out of 10, Exceptional, (35 reviews)
"Great property, loved our stay here! We will definitely stay here again! "
United States
Shawnnelle H.
The price is ￥28,656
￥89,198 total
includes taxes & fees
Feb 25 - Feb 26
HotTub-FirePit-8MintoWisp-Arcade-4BD-NoCleaningFee
Exterior

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, (13 reviews)
"Great spot for a team retreat!"
United States
Garrett H.
The price is ￥34,765
￥113,893 total
includes taxes & fees
Feb 17 - Feb 18
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
Terrace/patio

Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger!

Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger!
Oakland
10.0 out of 10, Exceptional, (23 reviews)
"We had an incredible time at the cabin and we're hoping to come back in the future. The house is BEAUTIFUL, the beds are comfortable, it's in a nice location, and the fire pit and hot tub were great as well. "
United States
Madeline C.
The price is ￥27,445
￥106,736 total
includes taxes & fees
Feb 25 - Feb 26
Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger!
Exterior

That Special Place

That Special Place
Oakland
10.0 out of 10, Exceptional, (30 reviews)
"We enjoyed our stay, beautiful cabin with a lake view.Would highly recommend this place, the host was super responsive to any questions we had. Easy check in and out. Kitchen well equipped, overall great experience."
United States
Rosemary C.
The price is ￥27,812
￥66,004 total
includes taxes & fees
Feb 16 - Feb 17
That Special Place
Property grounds

Deer Pass – Luxury Glamping Yurt Near Deep CreekMd

Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
Oakland
10.0 out of 10, Exceptional, (9 reviews)
"Great getaway"
United States
Holly M.
The price is ￥16,856
￥36,216 total
includes taxes & fees
Feb 23 - Feb 24
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
Exterior

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, (2 reviews)
"Great place to visit. Hope to come back next year"
United States
Stacy S.
The price is ￥40,298
￥50,162 total
includes taxes & fees
Feb 16 - Feb 17
Will O' The Wisp: 107B One Bedroom/One Bath
Smart TV, video games

In the heart of Deep Creek Lake! - "Shamrock Inn"

In the heart of Deep Creek Lake! - "Shamrock Inn"
Mountainside
9.6 out of 10, Exceptional, (5 reviews)
"Place was absolutely gorgeous host was very accommodating. Can't say enough good things about it"
United States
Michael M.
The price is ￥32,293
￥75,503 total
includes taxes & fees
Mar 3 - Mar 4
In the heart of Deep Creek Lake! - "Shamrock Inn"
Smart TV, fireplace, DVD player, books

The winter is coming !!!

The winter is coming !!!
Oakland
9.8 out of 10, Exceptional, (53 reviews)
"Very easy to check in and out! Thank you! "
United States
Edward
The price is ￥34,341
￥75,386 total
includes taxes & fees
Feb 16 - Feb 17
The winter is coming !!!
Interior

Suites at Silver Tree: A118 Studio Standard View

Suites at Silver Tree: A118 Studio Standard View
Oakland
10.0 out of 10, Exceptional, (3 reviews)
"Yes, we had a great time. Host was very accommodating."
United States
Anonymous traveler
The price is ￥33,337
￥42,876 total
includes taxes & fees
Feb 23 - Feb 24
Suites at Silver Tree: A118 Studio Standard View
Exterior

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

Will O' The Wisp: 105A Efficiency/One Bath
Oakland
9.6 out of 10, Exceptional, (23 reviews)
"Property is very nice. Looks exactly like the photos. "
United States
Debra M.
The price is ￥37,116
￥47,671 total
includes taxes & fees
Feb 16 - Feb 17
Will O' The Wisp: 105A Efficiency/One Bath
Interior

Suites at Silver Tree: A212 One Bedroom Standard View

Suites at Silver Tree: A212 One Bedroom Standard View
Oakland
The price is ￥31,679
￥40,660 total
includes taxes & fees
Feb 16 - Feb 17
Suites at Silver Tree: A212 One Bedroom Standard View
TV

Lakeview Chalet in Deep Creek Lake + Hot Tub

Lakeview Chalet in Deep Creek Lake + Hot Tub
Oakland
The price is ￥54,697
￥120,871 total
includes taxes & fees
Mar 9 - Mar 10
Lakeview Chalet in Deep Creek Lake + Hot Tub
Terrace/patio

Will O' The Wisp: 302B One Bedroom/One Bath

Will O' The Wisp: 302B One Bedroom/One Bath
Oakland
The price is ￥38,192
￥46,786 total
includes taxes & fees
Mar 15 - Mar 16
Will O' The Wisp: 302B One Bedroom/One Bath
Interior

2-bedroom log cabin oasis in soothing Deep Creek

2-bedroom log cabin oasis in soothing Deep Creek
Oakland
The price is ￥32,014
￥55,226 total
includes taxes & fees
Mar 5 - Mar 6
2-bedroom log cabin oasis in soothing Deep Creek
TV, fireplace, books

Wooded Retreat w Hot Tub, Loft, Game Room & Sauna

Wooded Retreat w Hot Tub, Loft, Game Room & Sauna
Oakland
10.0 out of 10, Exceptional, (1 review)
"Wonderful place for the perfect getaway! Just like the photos definitely worth every penny. Just have in mind that you are in the woods so the bugs are inevitable but the inside of the place was very clean.Me and my family took advantage of all the amenities from the grill, hot tub, fire place. Don't think twice and book this place!"
United States
Bonny S.
The price is ￥59,814
￥122,917 total
includes taxes & fees
Feb 26 - Feb 27
Wooded Retreat w Hot Tub, Loft, Game Room & Sauna
Living area

The Lake House at Silver Ridge

The Lake House at Silver Ridge
Silver Ridge
The price is ￥72,789
￥96,811 total
includes taxes & fees
Feb 25 - Feb 26
The Lake House at Silver Ridge
Interior

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, (3 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 ￥31,679
￥40,660 total
includes taxes & fees
Feb 16 - Feb 17
Suites at Silver Tree: A218 One Bedroom Standard View
Interior

Suites at Silver Tree: A216 Studio Standard View

Suites at Silver Tree: A216 Studio Standard View
Oakland
The price is ￥33,337
￥42,876 total
includes taxes & fees
Feb 25 - Feb 26
Suites at Silver Tree: A216 Studio Standard View
Interior

Suites at Silver Tree: A204 Studio Standard View

Suites at Silver Tree: A204 Studio Standard View
Oakland
The price is ￥33,514
￥43,079 total
includes taxes & fees
Feb 25 - Feb 26
Suites at Silver Tree: A204 Studio Standard View
Terrace/patio

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.
The price is ￥37,292
￥45,924 total
includes taxes & fees
Feb 23 - Feb 24
Will O' The Wisp: 103A Efficiency/One Bath
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

The Garrett Inn

The Garrett Inn

10/10 Excellent
"Comfortable, clean, across the street from a great eatery/bar and owners were a wonderful source of information in the surrounding area! Happy my husband found it!!!"
Jinx 1-night trip
Posted 3 days ago
The Garrett Inn

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. Some other top choices in Oakland are Sisters Treehouse and Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing .

How many vacation rentals are there in Oakland?

With 472 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.