Photo by Jenn Charbonneau

Oakland Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Tonight
Dec 28 - Dec 29
Tomorrow
Dec 29 - Dec 30
Next weekend
Jan 2 - Jan 4
In two weeks
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.
$1,455 nightly
The price is $1,611
Jan 1 - Jan 2, 2026
Total with taxes and fees
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.
$652 nightly
The price is $737
Jan 5 - Jan 6, 2026
Total with taxes and fees
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.
$393 nightly
The price is $445
Dec 30 - Dec 31
Total with taxes and fees
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.
$676 nightly
The price is $717
Jan 22 - Jan 23, 2026
Total with taxes and fees
Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger!
Terrace/patio
Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!

Cabin in Oakland

Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!
10.0 out of 10, Exceptional, (34)
"Great property, loved our stay here! We will definitely stay here again! "
United States
Shawnnelle H.
$675 nightly
The price is $764
Jan 8 - Jan 9, 2026
Total with taxes and fees
Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!
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.
$453 nightly
The price is $480
Jan 6 - Jan 7, 2026
Total with taxes and fees
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.
$445 nightly
The price is $472
Jan 5 - Jan 6, 2026
Total with taxes and fees
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.
$296 nightly
The price is $335
Jan 3 - Jan 4, 2026
Total with taxes and fees
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
$471 nightly
The price is $499
Jan 19 - Jan 20, 2026
Total with taxes and fees
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
$226 nightly
The price is $256
Jan 3 - Jan 4, 2026
Total with taxes and fees
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.
$296 nightly
The price is $335
Jan 1 - Jan 2, 2026
Total with taxes and fees
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
$277 nightly
The price is $314
Jan 3 - Jan 4, 2026
Total with taxes and fees
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
$237 nightly
The price is $267
Jan 8 - Jan 9, 2026
Total with taxes and fees
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
$1,357 nightly
The price is $1,438
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
$453 nightly
The price is $513
Jan 3 - Jan 4, 2026
Total with taxes and fees
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.
$263 nightly
The price is $299
Jan 3 - Jan 4, 2026
Total with taxes and fees
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.
$273 nightly
The price is $309
Jan 3 - Jan 4, 2026
Total with taxes and fees
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.
$234 nightly
The price is $264
Jan 1 - Jan 2, 2026
Total with taxes and fees
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.
$281 nightly
The price is $318
Jan 3 - Jan 4, 2026
Total with taxes and fees
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.
$297 nightly
The price is $336
Jan 8 - Jan 9, 2026
Total with taxes and fees
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.
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 Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

10/10 Excellent
"The host, Jeff was exceptionally proactive in communicating. The house is exactly as pictured and described. Even better than expected in person.The house had beautiful Christmas decorations and a very nice welcome basket. We traveled with two small dogs and there was room in the loft for their little beds. Carrying the puppies up and down the stairs was necessary due to steepness but that was expected. Just something to consider if that’s not your thing. Overall positive experience! "
Elisabeth H. 3-night trip
Posted 2 days ago
The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

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 $499 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. 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.