Oakland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Oakland vacation rentals

House (4 Bedrooms) | Front of property

Cedars on the Rocks by Taylor Made Deep Creek

Cedars on the Rocks by Taylor Made Deep Creek
3.5 star property
Oakland
10.0 out of 10, Exceptional, (1 review)
"Great stay. Very spacious and family friendly. Made me feel like home. Truly enjoyed the hot tub!!"
United States
DESIRAE
Cedars on the Rocks by Taylor Made Deep Creek
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 ￥35,714
￥116,835 total
includes taxes & fees
Apr 7 - Apr 8
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
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 ￥39,557
￥49,636 total
includes taxes & fees
Apr 13 - Apr 14
Will O' The Wisp: 107B One Bedroom/One Bath
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 ￥17,460
￥36,841 total
includes taxes & fees
Apr 7 - Apr 8
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
Terrace/patio

“Moonbeam” (Airstream)

“Moonbeam” (Airstream)
Oakland
10.0 out of 10, Exceptional, (3 reviews)
"Moonbeam was nice and outdoor space was awesome. We walked the trail and had dinner in Deep Creek.. Highly recommend "
United States
Scott H.
The price is ￥18,254
￥35,937 total
includes taxes & fees
Apr 14 - Apr 15
“Moonbeam” (Airstream)
Interior

Suites at Silver Tree: A204 Studio Standard View

Suites at Silver Tree: A204 Studio Standard View
Oakland
The price is ￥32,814
￥41,781 total
includes taxes & fees
Apr 5 - Apr 6
Suites at Silver Tree: A204 Studio Standard View
Exterior

That Special Place

That Special Place
Oakland
10.0 out of 10, Exceptional, (30 reviews)
"Had a great time. House was great."
United States
Russell J.
The price is ￥28,429
￥67,488 total
includes taxes & fees
Apr 14 - Apr 15
That Special Place
Exterior

Will O' The Wisp: 206A Efficiency/One Bath

Will O' The Wisp: 206A Efficiency/One Bath
Oakland
9.6 out of 10, Exceptional, (16 reviews)
"Absolutely amazing. Perfect getaway! Clean, well stocked, and perfect size for a couple or small family. We watched the full moon from our balcony. It was our first trip to Deep Creek, and we can’t wait to return. The staff is friendly and helpful. We will book again soon. "
United States
tish p.
The price is ￥36,321
￥45,613 total
includes taxes & fees
Apr 13 - Apr 14
Will O' The Wisp: 206A Efficiency/One Bath
Terrace/patio

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

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

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
The price is ￥63,103
￥130,320 total
includes taxes & fees
Apr 15 - Apr 16
Luxury Deep Creek Lake Cabin • Sauna • Hot Tub • Arcade • Fire Pit •Pet Friendly
Interior

Suites at Silver Tree: A212 One Bedroom Standard View

Suites at Silver Tree: A212 One Bedroom Standard View
Oakland
The price is ￥31,103
￥38,822 total
includes taxes & fees
Apr 6 - Apr 7
Suites at Silver Tree: A212 One Bedroom Standard View
Smart TV, fireplace, video games, DVD player

Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.

Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.
Oakland
9.6 out of 10, Exceptional, (5 reviews)
"The place was so clean and fully stocked. We had a wonderful stay. Five stars!! "
United States
Lori S.
The price is ￥57,532
￥114,220 total
includes taxes & fees
Apr 24 - Apr 25
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.
TV, fireplace

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 ￥45,981
￥106,657 total
includes taxes & fees
Apr 12 - Apr 13
Wooded Retreat w Hot Tub, Loft, Game Room & Sauna
Exterior

Luxor Mountaintop Cabin-Castle at Deep Creek Lake

Luxor Mountaintop Cabin-Castle at Deep Creek Lake
Oakland
The price is ￥66,161
￥130,098 total
includes taxes & fees
Apr 27 - Apr 28
Luxor Mountaintop Cabin-Castle at Deep Creek Lake
Interior

Suites at Silver Tree: A314 Studio & Loft Standard View

Suites at Silver Tree: A314 Studio & Loft Standard View
Oakland
10.0 out of 10, Exceptional, (9 reviews)
"Unique, fun architecture near many recreational activities "
United States
Kathleen
The price is ￥38,886
￥49,378 total
includes taxes & fees
Apr 5 - Apr 6
Suites at Silver Tree: A314 Studio & Loft Standard View
Interior

Suites at Silver Tree: A118 Studio Standard View

Suites at Silver Tree: A118 Studio Standard View
Oakland
10.0 out of 10, Exceptional, (5 reviews)
"Yes, we had a great time. Host was very accommodating."
United States
Anonymous traveler
The price is ￥32,632
￥40,732 total
includes taxes & fees
Apr 9 - Apr 10
Suites at Silver Tree: A118 Studio Standard View
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 ￥31,103
￥38,822 total
includes taxes & fees
Apr 5 - Apr 6
Suites at Silver Tree: A218 One Bedroom 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, (24 reviews)
"Property is very nice. Looks exactly like the photos. "
United States
Debra M.
The price is ￥36,321
￥45,613 total
includes taxes & fees
Apr 13 - Apr 14
Will O' The Wisp: 105A Efficiency/One Bath
Interior

Suites at Silver Tree: A310 Studio & Loft Standard View

Suites at Silver Tree: A310 Studio & Loft Standard View
Oakland
10.0 out of 10, Exceptional, (4 reviews)
"Didn't get to enjoy the view because it was raining on and off. The place was great and view by the lake was wonderful."
United States
Eric F.
The price is ￥38,886
￥49,883 total
includes taxes & fees
Apr 7 - Apr 8
Suites at Silver Tree: A310 Studio & Loft Standard View
Interior

Suites at Silver Tree: A216 Studio Standard View

Suites at Silver Tree: A216 Studio Standard View
Oakland
The price is ￥32,632
￥41,405 total
includes taxes & fees
Apr 5 - Apr 6
Suites at Silver Tree: A216 Studio 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oakland Hotel Reviews

The Garrett Inn

The Garrett Inn

10/10 Excellent
"Nice place we would stay again. Some road noise but by 10 it was quiet. He place is dated but the room was spacious and the staf wa great."
James 1-night trip
Posted 13 hours 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 Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp and Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit.

How many vacation rentals are there in Oakland?

With 468 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.