Photo by Jenn Charbonneau

Oakland Holiday Rentals

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Our top choices for Oakland holiday rentals

10.0 out of 10, Exceptional, (118)
"Nice clean home. Good central location "
United States
carla z.
Level lakefront, family-friendly, hot tub, low fees, private dock
8.2 out of 10, Very good, (65)
"We had a great time and the place was exactly as advertised, it was perfect."
United States
John K.
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Cabin in Oakland

The winter is coming !!!
9.8 out of 10, Exceptional, (49)
"Very easy to check in and out! Thank you! "
United States
Edward
The price is NZ$699
includes taxes & fees
16 Dec - 17 Dec
The winter is coming !!!
10.0 out of 10, Exceptional, (86)
"As advertised! Very comfortable. A wonderful getaway!"
United States
Joanna C.
Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing
9.6 out of 10, Exceptional, (55)
"A great backdrop for a mini family reunion."
United States
Nora V.
Amazing Central Location! Lakefront! Hot tub/dock!
10.0 out of 10, Exceptional, (41)
"The property was beautiful and we had a very relaxing stay"
United States
Courtney U.
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit
10.0 out of 10, Exceptional, (51)
"This house was actually as beautiful as the pictures! We had a great stay and hope to return in the future."
United States
Sandra R.
Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip
9.8 out of 10, Exceptional, (262)
"Very homey and great layout! Already planning on coming back!"
United States
Agnes H.
Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek
10.0 out of 10, Exceptional, (3)
"Perfect location for our anniversary trip. "
United States
Natalie M.
3-bed, charming modernized cottage tucked into wooded hillside in Deep Creek, MD
10.0 out of 10, Exceptional, (3)
"the property was clean, spacious, close to the lake. We enjoyed the firepit and the hot tub. The Kitchen was well stocked. We had everything we needed."
United States
Susan L.
Dockside Bliss w/ Hot Tub, Fire Pit & Big Deck
10.0 out of 10, Exceptional, (8)
"Super comfortable, clean, beautiful, thoughtful and stylish design, good location, nice size for a small family. It’s the best place I have ever stayed. We will definitely come back again!"
United States
Kaoru M.
EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub
10.0 out of 10, Exceptional, (32)
"Fantastic house! Everything was exactly as described, and absolutely perfect! We enjoyed every min of our stay, will definitely come back again soon "
United States
John B.
The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek
10.0 out of 10, Exceptional, (82)
"Incredible house and even better location! Convenient to everything by boat or car, and minimal woke zone makes it perfect for hanging in the dock! "
United States
Alex D.
Mt. Dew- AMAZING LAKE FRONT! 7 BR Home with Hot Tub, Fire Pit, Dock, Pool Table
8.6 out of 10, Excellent, (12)
"In town to celebrate daughter Graduating from college! Great house, beds so comfy!!! House had all we needed & views are amazing! "
United States
B.J. B.
5BR lakefront retreat with hot tub, sauna, & dock
9.2 out of 10, Wonderful, (37)
"We had a wonderful long weekend, the location is perfect and the owners seem to work hard at making the cottage feel like home. The fire pit was awesome, too!"
United States
Margaret K.
Dog-friendly secluded cabin with hot tub, firepit, lawn games, & great deck

Cabin in Oakland

Cabin in the Woods
10.0 out of 10, Exceptional, (21)
"Amazing place "
United States
D W.
Cabin in the Woods
9.6 out of 10, Exceptional, (17)
"The studio apt. is roomy and very comfy! The decor is exceptional! the view is outstanding! Enjoyed our trip very much!"
United States
John F.
Will O' The Wisp: 714H Studio Loft/One Bath
9.6 out of 10, Exceptional, (15)
"Nice place for a weekend getaway"
United States
Margaret V.
Modern Lakefront A-Frame! Hot Tub + Fire Pit + Fenced Yard

Holiday Home in Oakland

Sisters Treehouse
9.4 out of 10, Exceptional, (103)
"Very happy with the property, the decor inside was beautiful. Loved the master suite upstairs,with the great view of the lake. The house was spotless and very comfortable and a great location. "
United States
Lynda Z.
Sisters Treehouse
9.4 out of 10, Exceptional, (16)
"We had a blast at this wooded oasis. Tons of space and cozy rooms for every guest. Would love to book again. "
United States
Sam P.
Luxury Log Chalet w/ Pool & Fireplace
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

Find out more about Oakland

Everything you need to know about Oakland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakland holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland holiday rentals we have selected for you start as low as NZ$699 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Oakland has to offer?

Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing : This highly rated holiday home rental in Oakland is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Some other top choices in Oakland are Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit and Amazing Central Location! Lakefront! Hot tub/dock!.

How many holiday rentals are there in Oakland?

With 463 Expedia holiday rentals, you're guaranteed 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 holiday rental in Oakland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakland. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.