Holiday Rentals Oakland from £271: Find Short-Term Rentals & Holiday Accommodations

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Top Holiday Rentals in Oakland

Relax on the deck with a sofa and chairs, taking in the serene views of the surrounding water and lush trees.

"This was perfect for our family’s ski weekend at Wisp with our teens. We loved the hot tub, fireplace, and close proximity to restaurants. We’ll come back again!"

Enjoy cooking in this well-equipped kitchen with a refrigerator, dishwasher, and sink.

"This was my first time staying with VRBO. It was a million dollar view. There were just a few minor things that were mentioned before on other reviews that were not taken care of such as the hole in the master bedroom door, the smell of sewage in the kitchen the garbage disposal area, and also the stairs down to the dock area didn't seem too stable. I would have liked to have seen the fountain on but I do realize it's earlier in the year. The owners may want to change the curtains because not...

Escape to a secluded cabin surrounded by forest views, featuring a hot tub and wooden deck.

"Loved the location of this beautiful cabin - while the weather wasn’t always ideal for outdoor activities during our time in Deep Creek, we enjoyed spending time in the cabin!"

Relax in this spacious living room with a high ceiling, featuring a large flat-screen TV and comfortable sofa.

"Other than a hell of a lot of mosquitos being inside the home everything else was perfect after about an hour or 2 they were gone or maybe after a few drinks but I will be booking again the home was amazing"

Stunning interior with a high ceiling, exposed beams, and a staircase leading to an upper level.

"We had a great stay! Thank goodness for the dryer to dry our snow gear to keep us out on the slopes! The place awesome! And the host is great to work with and very responsive to needs!! Would love to come back again in the summer! Definitely recommend to anyone!"

includes taxes & fees

13 Jul - 14 Jul

Enjoy a serene riverside retreat with a deck, perfect for taking in the tranquil views.

"The property was clean, comfortable and well stocked."

Relax on a cozy bench surrounded by a serene wooded area.

"This was our favorite of all the vacation rentals we have done. The cabin is charming and the amenities outstanding. The hot tub and firepit in the yard are great. We really enjoyed our stay"

Relax on the deck with comfortable seating and enjoy the serene views of the surrounding landscape.

"We had such a nice stay at the tiny house! The inside was adorable and the location is perfect. The views were beautiful and there were lots of hiking trails and delicious food nearby. We definitely plan to come back for another stay soon!"

Enjoy cooking in this well-equipped kitchen with a central island, appliances, and a dining area.

"Host had great communication and was very friendly. Space was clean and welcoming. We loved the view, as well as how close it is to Wisp. We would stay again! "

Cozy cabin-style accommodation with a stone fireplace, central fan, and sliding glass door to a deck with outdoor seating.

"Nice place for a weekend getaway"

Relax on the deck with a fire pit, surrounded by tall trees in a secluded forest setting.

"Communication was excellent (the most thorough welcome email I've ever received!)Very thoughtfully stocked (books, videos, marshmallows, etc)Lighting and decor created a very cozy ambianceClose to every place we wanted to go to (Wisp, Deep Creek State Park, Firewater, etc)"

Enjoy meal preparation and dining in this well-equipped kitchen with a stove, dishwasher, and sink.

"My family and I had a great time at the Red Cottage. We would definitely stay here again."

Relax on the deck with a chair and table, surrounded by large windows and a convenient entrance.

"The property was exactly as advertised and just what we wanted from our weekend!"

Enjoy cooking in this well-equipped kitchen with an oven, coffee maker, and toaster.

"Great family place. House is as described. User friendly appliances, tv’s and hot tub! All 14 of us enjoyed our stay."

Cozy bedroom with a large bed, ceiling fan, and windows with blinds.

"I absolutely loved staying at the Love Shack! It was really cozy and cute. It’s dog friendly which was great! The hot tub was a great little add on to the property and the cabin is close to a lot of great places. We would definitely stay here again!"

Relax in this inviting living room with a sofa, armchair, and fireplace, perfect for unwinding.

"Property was wonderful. Location was great. Enjoyed our stay at this property. Thank you for letting us use your place."

Relax on the deck with a wooden table and chairs, shaded by a large umbrella, surrounded by lush trees and greenery.

"We had a great time, the location was great and the place was clean"

Relax in this inviting living room with a fireplace, sectional sofa, and sliding glass door to an outdoor area.

"Enjoyed our stay..location is great..close to restaurants and entertainment. "

Enjoy cooking in this well-lit kitchen with dishwasher, oven, and microwave.

"We enjoyed our stay and the peace of this lovely home very much!"

Enjoy cooking in this well-equipped kitchen with a large island, granite countertop, and stainless steel stove.

"Great stay, beautiful home and location which met all of our needs. Would highly recommend. Only complaint was grass was over a foot high when we arrived, looked like it hadn't been cut this year and made the yard unusable. However, after calling to report the yard condition a crew came out and got everything mowed. They were very nice and apologetic about the yard condition and had the property mowed and we were able to then use the yard."

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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, apart-hotels, 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 £271 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.

Recent reviews of Oakland properties

Lakefront, dog friendly, dock slip, hot tub, and fire pit

5/5 Excellent

Family Vaykay

"We had a wonderful vacation! The reservation and check-in process was extremely easy and streamlined! The property and home was beautiful and met all of our needs. Amenities were all inclusive! Outdoor hot tub and use of kayaks and paddleboards were awesome! We highly recommend this property! "

A verified traveller stayed at Lakefront, dog friendly, dock slip, hot tub, and fire pit

Posted 6 days ago

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

5/5 Excellent

Prefect Get away!!

"We had an amazing getaway at the Tiny House visiting from Washington, D.C. area for a couple of days. The property manager was easy to reach and made the check-in process seamless. When we first arrived, the place was a bit warm, likely due to the time of day, but it cooled down by the evening. The manager provided excellent recommendations for activities, including hiking, dining options, and a beach area for us and our dogs. We really enjoyed our stay and would definitely come back again!"

A verified traveller stayed at The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

Posted 2 weeks ago

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

5/5 Excellent

Great cabin by the lake

"It was perfect for our weekend stay. A lovely cabin on the hill with views of the lake and great lawn space for kids and pets. The space is clean and comes with linens, towels, and kitchen accessories, making it easy to have a quick or extended stay. "

A verified traveller stayed at Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Posted 2 weeks ago

5/5 Excellent

Great experience!!!

"Property just as described and included lots of deer and even a bear sighting It rained the entire time but we didn't mind b/c Cabin was awesome. Had to get used to gated community access but once we figured it out we loved it.... can even have packages delivered to office outside front gate. Would definitely stay again!"

A verified traveller stayed at Cabin in the Woods

Posted 3 weeks ago

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

5/5 Excellent

"Great little spot for three younger people looking to explore the area. Four would have been a tight squeeze. Spiral staircase that is used to access 2/3 sleeping areas was also a tighter squeeze. Owner was communicative and responsive. Pleasant little weekend!"

A verified traveller stayed at In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Posted 1 month ago

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?

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp: This highly rated holiday home rental in Oakland offers a fireplace, a selection of games and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub. Some other top choices in Oakland are Dog-friendly house on the lake, central AC, & EV charger and Modern house on the lake with private dock, hot tub, air hockey & central AC.

How many holiday rentals are there in Oakland?

With 561 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.

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Top Holiday Rentals in Oakland

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Dog-friendly house on the lake, central AC, & EV charger

Dog-friendly house on the lake, central AC, & EV charger

EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

Modern house on the lake with private dock, hot tub, air hockey & central AC

Modern house on the lake with private dock, hot tub, air hockey & central AC

Lake Loft at Deep Creek Lake

Lake Loft at Deep Creek Lake

Bright condo with Deep Creek Lake views, wood fireplace

Bright condo with Deep Creek Lake views, wood fireplace

Cabin in the Woods

Cabin in the Woods

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

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

Deep Creek Lake Townhome w/ Deck & Water Views

Deep Creek Lake Townhome w/ Deck & Water Views

New Construction! Modern Lakefront A-Frame with Hot Tub + Fire Pit

New Construction! Modern Lakefront A-Frame with Hot Tub + Fire Pit

Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek

Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek

Charming Dog Friendly Cottage w/ Dock & Fire Pit

Charming Dog Friendly Cottage w/ Dock & Fire Pit

Charming home with furnished deck & lake view - walking distance to shops

Charming home with furnished deck & lake view - walking distance to shops

Huge, Beautiful and Quiet Home with Amazing Amenities

Huge, Beautiful and Quiet Home with Amazing Amenities

The Love Shack-- The BEST Couples and Small Family Retreat at Deep Creek Lake!

The Love Shack-- The BEST Couples and Small Family Retreat at Deep Creek Lake!

Sisters Treehouse

Sisters Treehouse

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi

Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi

Lakefront, dog friendly, dock slip, hot tub, and fire pit

Lakefront, dog friendly, dock slip, hot tub, and fire pit

Log Retreat: Lake Access, Dogs Welcome, Dock Slip, 2 Hot Tubs!

Log Retreat: Lake Access, Dogs Welcome, Dock Slip, 2 Hot Tubs!

Find out more about Oakland

Find out more about Oakland

Recent reviews of Oakland properties

Recent reviews of Oakland properties

Lakefront, dog friendly, dock slip, hot tub, and fire pit

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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