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Oakland Vacation Rentals

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Check prices for these dates

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Dec 30 - Dec 31
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Dec 31 - Jan 1
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Oakland vacation rentals

Fridge, microwave, oven, stovetop
Wooded Retreat w Hot Tub, Loft, Game Room & Sauna

Chalet in Oakland

Wooded Retreat w Hot Tub, Loft, Game Room & Sauna
10.0 out of 10, Exceptional, (1)
"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 ￥139,319
￥209,230 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Wooded Retreat w Hot Tub, Loft, Game Room & Sauna
Property grounds
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

Cabin in Oakland

New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
2.0 star property
10.0 out of 10, Exceptional, (13)
"The stay was great! Everyone loved the location and all the amenities provided! It was a great get away for all of our friends to get together and hangout! "
United States
Becca V.
The price is ￥35,093
￥114,968 total
includes taxes & fees
Jan 5 - Jan 6, 2026
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
Exterior
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.

Chalet in Oakland

Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.
10.0 out of 10, Exceptional, (4)
"The place was so clean and fully stocked. We had a wonderful stay. Five stars!! "
United States
Lori S.
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.
Terrace/patio
Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger!

Cabin in Oakland

Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger!
10.0 out of 10, Exceptional, (19)
"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 ￥31,038
￥111,762 total
includes taxes & fees
Jan 22 - Jan 23, 2026
Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger!
4 bedrooms, desk, soundproofing, iron/ironing board
Jamesons Cabin! Hot Tub, Fire Pit, Arcade, Coffee Bar, all 8 Minutes to Wisp!

Cabin in Oakland

Jamesons Cabin! Hot Tub, Fire Pit, Arcade, Coffee Bar, all 8 Minutes to Wisp!
10.0 out of 10, Exceptional, (35)
"Great property, loved our stay here! We will definitely stay here again! "
United States
Shawnnelle H.
The price is ￥43,516
￥109,129 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Jamesons Cabin! Hot Tub, Fire Pit, Arcade, Coffee Bar, all 8 Minutes to Wisp!
Fridge, microwave, oven, stovetop
That Special Place

Cabin in Oakland

That Special Place
10.0 out of 10, Exceptional, (26)
"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 ￥32,230
￥71,627 total
includes taxes & fees
Jan 7 - Jan 8, 2026
That Special Place
Smart TV, video games
In the heart of Deep Creek Lake! - "Shamrock Inn"

Vacation Home in Mountainside

In the heart of Deep Creek Lake! - "Shamrock Inn"
9.6 out of 10, Exceptional, (5)
"Place was absolutely gorgeous host was very accommodating. Can't say enough good things about it"
United States
Michael M.
The price is ￥29,338
￥72,762 total
includes taxes & fees
Jan 5 - Jan 6, 2026
In the heart of Deep Creek Lake! - "Shamrock Inn"
Beach
Will O' The Wisp: 107B One Bedroom/One Bath

Condo in Mountainside

Will O' The Wisp: 107B One Bedroom/One Bath
10.0 out of 10, Exceptional, (2)
"Great place to visit. Hope to come back next year"
United States
Stacy S.
The price is ￥41,015
￥50,063 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Will O' The Wisp: 107B One Bedroom/One Bath
Exterior
The winter is coming !!!

Cabin in Oakland

The winter is coming !!!
9.8 out of 10, Exceptional, (50)
"Very easy to check in and out! Thank you! "
United States
Edward
The price is ￥36,357
￥78,052 total
includes taxes & fees
Jan 19 - Jan 20, 2026
The winter is coming !!!
Interior
Suites at Silver Tree: A118 Studio Standard View

Aparthotel in Oakland

Suites at Silver Tree: A118 Studio Standard View
10.0 out of 10, Exceptional, (2)
"Yes, we had a great time. Host was very accommodating."
United States
Anonymous traveler
The price is ￥32,064
￥39,858 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Suites at Silver Tree: A118 Studio Standard View
Beach
Will O' The Wisp: 207B One Bedroom/One Bath

Condo in Oakland

Will O' The Wisp: 207B One Bedroom/One Bath
10.0 out of 10, Exceptional, (5)
"Very nice place."
United States
Ronald D.
The price is ￥40,836
￥52,008 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Will O' The Wisp: 207B One Bedroom/One Bath
Indoor pool, a heated pool
Will O' The Wisp: 302B One Bedroom/One Bath

Condo in Oakland

Will O' The Wisp: 302B One Bedroom/One Bath
2.0 star property
The price is ￥38,872
￥49,603 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Will O' The Wisp: 302B One Bedroom/One Bath
Interior
Suites at Silver Tree: A212 One Bedroom Standard View

Aparthotel in Oakland

Suites at Silver Tree: A212 One Bedroom Standard View
2.0 star property
The price is ￥32,244
￥41,716 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Suites at Silver Tree: A212 One Bedroom Standard View
Fridge, microwave, oven, stovetop
Private Lodge sleeps 25 guests Spectacular Views

Vacation Home in Oakland

Private Lodge sleeps 25 guests Spectacular Views
The price is ￥101,178
￥224,301 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Private Lodge sleeps 25 guests Spectacular Views
Indoor pool, a heated pool
Will O' The Wisp: 501F Three Bedroom/Two Bath

Condo in Mountainside

Will O' The Wisp: 501F Three Bedroom/Two Bath
10.0 out of 10, Exceptional, (1)
"Was a beautiful condo! We had a great time kids loved the beach area "
United States
Chelsy H.
The price is ￥65,273
￥83,835 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Will O' The Wisp: 501F Three Bedroom/Two Bath
Beach
Will O' The Wisp: 103A Efficiency/One Bath

Condo in Oakland

Will O' The Wisp: 103A Efficiency/One Bath
9.6 out of 10, Exceptional, (8)
"This was my first time at Deep Creek, and I can’t wait to go back. The property was well maintained, and we loved the amenities available to us. We spent most of the weekend on the beach/docks directly out front, but also took advantage of the pool, spa, and sauna. Check in/out was easy, and all of the people we ran into were friendly. We will definitely be returning. "
United States
Alice F.
The price is ￥37,957
￥48,892 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Will O' The Wisp: 103A Efficiency/One Bath
Beach
Will O' The Wisp: 205A Efficiency/One Bath

Condo in Oakland

Will O' The Wisp: 205A Efficiency/One Bath
9.4 out of 10, Exceptional, (10)
"Nice place to stay, quiet and relaxing, and the restaurant was amazing!"
United States
Anson P.
Will O' The Wisp: 205A Efficiency/One Bath
Interior
Suites at Silver Tree: A210 Studio Standard View

Aparthotel in Oakland

Suites at Silver Tree: A210 Studio Standard View
10.0 out of 10, Exceptional, (2)
"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.
The price is ￥32,244
￥41,055 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Suites at Silver Tree: A210 Studio Standard View
Interior
Suites at Silver Tree: A318 One Bedroom & Loft Standard View

Aparthotel in Oakland

Suites at Silver Tree: A318 One Bedroom & Loft Standard View
10.0 out of 10, Exceptional, (2)
"We can’t wait to come back! It was a great stay!"
United States
Kari H.
The price is ￥40,635
￥52,275 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Suites at Silver Tree: A318 One Bedroom & Loft Standard View
Beach
Will O' The Wisp: 104B One Bedroom/One Bath

Condo in Oakland

Will O' The Wisp: 104B One Bedroom/One Bath
10.0 out of 10, Exceptional, (1)
"The property is perfectly located to all sorts of attractions. Both restaurants on the property are great spots to eat at. The condo was lovely, but our trip was just a touch to early in the season to have the patio furniture out. Even without it we were able to sit at the beach and close to the lake with the benches provided. All in all great weekend get away!"
United States
Jessica P.
The price is ￥40,836
￥50,851 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Will O' The Wisp: 104B One Bedroom/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

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

10/10 Excellent
"Very welcoming"
Tim B. 4-night trip
Posted 1 day ago
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

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 Amazing Central Location! Lakefront! Hot tub/dock! and Level lakefront, family-friendly, hot tub, low fees, private dock.

How many vacation rentals are there in Oakland?

With 464 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.