Oakland Vacation Rentals

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In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Oakland vacation rentals

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.
$205 nightly
The price is $232
Apr 15 - Apr 16
Total with taxes and fees
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
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.
$689 nightly
The price is $779
May 4 - May 5
Total with taxes and fees
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)
"A peaceful and pretty place to stay at."
United States
Selena
$685 nightly
The price is $726
May 6 - May 7
Total with taxes and fees
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, (31 reviews)
"Had a great time. House was great."
United States
Russell J.
$399 nightly
The price is $423
Apr 15 - Apr 16
Total with taxes and fees
That Special Place
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.
$269 nightly
The price is $305
Apr 17 - Apr 18
Total with taxes and fees
Will O' The Wisp: 107B One Bedroom/One Bath
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.
$200 nightly
The price is $226
Apr 15 - Apr 16
Total with taxes and fees
“Moonbeam” (Airstream)
Interior

Suites at Silver Tree: A216 Studio Standard View

Suites at Silver Tree: A216 Studio Standard View
Oakland
$233 nightly
The price is $263
Apr 21 - Apr 22
Total with taxes and fees
Suites at Silver Tree: A216 Studio Standard View
Exterior

Will O' The Wisp: 205A Efficiency/One Bath

Will O' The Wisp: 205A Efficiency/One Bath
Oakland
9.4 out of 10, Exceptional, (10 reviews)
"Place was very cozy and clean perfect for a weekend getaway! Definitely plan on staying there again in the future!"
United States
Raymond K.
$253 nightly
The price is $286
Apr 26 - Apr 27
Total with taxes and fees
Will O' The Wisp: 205A Efficiency/One Bath
TV

Lakeview Chalet in Deep Creek Lake + Hot Tub

Lakeview Chalet in Deep Creek Lake + Hot Tub
Oakland
10.0 out of 10, Exceptional, (1 review)
"Place was very clean and tidy upon arrival! Would rent here again "
United States
Tyrone C.
$585 nightly
The price is $621
Apr 16 - Apr 17
Total with taxes and fees
Lakeview Chalet in Deep Creek Lake + Hot Tub
Interior

Suites at Silver Tree: A212 One Bedroom Standard View

Suites at Silver Tree: A212 One Bedroom Standard View
Oakland
$216 nightly
The price is $245
Apr 23 - Apr 24
Total with taxes and fees
Suites at Silver Tree: A212 One Bedroom Standard View
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.
$686 nightly
The price is $755
Apr 20 - Apr 21
Total with taxes and fees
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
$782 nightly
The price is $829
May 6 - May 7
Total with taxes and fees
Luxor Mountaintop Cabin-Castle at Deep Creek Lake
Interior

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)
"Yes, we had a great time. Host was very accommodating."
United States
Anonymous traveler
$233 nightly
The price is $263
Apr 21 - Apr 22
Total with taxes and fees
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
$216 nightly
The price is $245
Apr 21 - Apr 22
Total with taxes and fees
Suites at Silver Tree: A218 One Bedroom Standard View
Interior

Suites at Silver Tree: B104 One Bedroom Lake View

Suites at Silver Tree: B104 One Bedroom Lake View
Oakland
$287 nightly
The price is $325
Apr 17 - Apr 18
Total with taxes and fees
Suites at Silver Tree: B104 One Bedroom Lake View
Interior

Suites at Silver Tree: A125 Studio Lake View

Suites at Silver Tree: A125 Studio Lake View
Oakland
$268 nightly
The price is $302
Apr 21 - Apr 22
Total with taxes and fees
Suites at Silver Tree: A125 Studio Lake View
Interior

Suites at Silver Tree: A204 Studio Standard View

Suites at Silver Tree: A204 Studio Standard View
Oakland
$234 nightly
The price is $264
Apr 21 - Apr 22
Total with taxes and fees
Suites at Silver Tree: A204 Studio Standard View
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
$277 nightly
The price is $313
Apr 21 - Apr 22
Total with taxes and fees
Suites at Silver Tree: A314 Studio & Loft Standard View
Interior

Suites at Silver Tree: A310 Studio & Loft Standard View

Suites at Silver Tree: A310 Studio & Loft Standard View
Oakland
9.6 out of 10, Exceptional, (5 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.
$271 nightly
The price is $307
Apr 26 - Apr 27
Total with taxes and fees
Suites at Silver Tree: A310 Studio & Loft Standard View
Interior

Suites at Silver Tree: A210 Studio Standard View

Suites at Silver Tree: A210 Studio Standard View
Oakland
10.0 out of 10, Exceptional, (3 reviews)
"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
Apr 21 - Apr 22
Total with taxes and fees
Suites at Silver Tree: A210 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.
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Top Oakland Hotel Reviews

The Garrett Inn

The Garrett Inn

10/10 Excellent
"Superb hotel in every respect. "
Debra 1-night trip
Posted 20 hours ago
The Garrett Inn

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 $423 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 Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp and Lakefront/Dock/Amazing views HotTub.

How many vacation rentals are there in Oakland?

With 471 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.