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Oakland Holiday Rentals

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Holiday Rentals in Oakland

Southern Oregon Cabin: Fire Pit & Private Pond!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Cute little place! Especially liked the patio and outside areas. Inside needs a few finishing touches like coat hooks on back of doors, but place is very new, clean and worked great for our few days there."
Southern Oregon Cabin: Fire Pit & Private Pond!

Romantic Vineyard Getaway in Oakland: Mtn Views!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Property was well organized with all the necessities/amenities that made our stay that much more comfortable. Perhaps instructions on how to operate front door lock would be helpful. Otherwise, everything else was perfect. Thank you! "
Romantic Vineyard Getaway in Oakland: Mtn Views!

Southern Oregon Cabin: Fire Pit & Private Pond!

2.0 star property
9.4 out of 10, Exceptional, (3)
"I needed a break from life for a moment and the chaos of what is my home and this little slice of heaven was everything!!! the sounds of nature. the ducks and geese. the privacy and seclusion. it was quite literally heaven on earth for me. also dog friendly. my puppy loved the outdoors"
Southern Oregon Cabin: Fire Pit & Private Pond!

Romantic Vineyard Getaway in Oakland: Mtn Views!

8.0 out of 10, Very good, (4)
"There were indications that the “kitchenette” at least appeared to have a counter- top toaster oven and a bbq was available on patio. Neither was available. The location is remote requiring guest to travel into town for all meals"
Romantic Vineyard Getaway in Oakland: Mtn Views!

Vineyard Farmhouse in Oakland w/ Hot Tub!

3.0 star property
Vineyard Farmhouse in Oakland w/ Hot Tub!

Vineyard Farmhouse in Oakland w/ Hot Tub!

10.0 out of 10, Exceptional, (2)
"The house slept 16 & was very spacious & gorgeous!! We had a wonderful time."
Vineyard Farmhouse in Oakland w/ Hot Tub!

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

9.8 out of 10, Exceptional, (79)
"Love this little abode and recommend "
The price is NZ$365
includes taxes & fees
16 July - 17 July
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

Great Vintage 2500sq ft. country cabin amazing river front setting!

9.6 out of 10, Exceptional, (217)
"Private, views are incredible and perfectly situated. "
The price is NZ$853
includes taxes & fees
20 July - 21 July
Great Vintage 2500sq ft. country cabin amazing river front setting!

Tiny House nestled into the Forest on 160 acre Playground.

9.0 out of 10, Wonderful, (6)
"We had an amazing time here it was so quite and peaceful and the host were amazing we will be going back"
The price is NZ$261
includes taxes & fees
13 July - 14 July
Tiny House nestled into the Forest on 160 acre Playground.

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (33)
"Peaceful and clean."
The price is NZ$306
includes taxes & fees
16 July - 17 July
A Restful Studio Near a Creek and Forest - Pets

Lil Cedar Lodge

The price is NZ$186
includes taxes & fees
20 July - 21 July
Lil Cedar Lodge

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (25)
"We have stayed at this property now multiple times and it has been clean, easy, great location, everything works and we will definitely be back"
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

Lake front LAWN FLOOR of bi-level home. bottom floor only. private entrance.

10.0 out of 10, Exceptional, (11)
"Great place for our extend family to stay while attending USTAF Junior nationals. Beautiful location and nice and quiet. We enjoyed our stay."
Lake front LAWN FLOOR of bi-level home. bottom floor only. private entrance.

Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

9.8 out of 10, Exceptional, (29)
"This place is a great place to stay. Clean, property manager is great, location is a close drive to anything you need. This was our second time there. Will be back again if we are in the area. "
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (59)
"Such a homey and beautiful house and property. Perfect weather. My whole family is already asking to go back!"
Firewater Lodge Cabin Experience

Lake View House

10.0 out of 10, Exceptional, (34)
"Needed a place to post up for a week. Great location, plenty of room, well taken care of. "
Lake View House

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (38)
"We stayed here for a night since we had a nearby disc golf tournament. Leah was a great host and the house was super clean and comfy. Quiet neighborhood, cool back porch to hang out. Highly recommend! Thank you Leah!"
The price is NZ$575
includes taxes & fees
14 July - 15 July
The Watusi Place - A Modern Umpqua Valley Getaway

70s Retro Lounge

10.0 out of 10, Exceptional, (4)
"Renee was an absolute delight to communicate with and I’m appreciative of her hospitality. This place is absolutely adorable and secluded. It was a nice and peaceful New Year’s Eve. "
70s Retro Lounge

Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews

9.8 out of 10, Exceptional, (20)
"Very clean property with plenty of amenities. Very short walk to downtown shops and eating. One of the nicest properties that I have stayed at. Looking forward to staying here again if in the area."
The price is NZ$529
includes taxes & fees
13 July - 14 July
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews

Xenia House-Roseburg Retreat with a View! Near Wildlife Safari

9.6 out of 10, Exceptional, (18)
"Very clean and we loved how well stocked it was! Thankful for the garage to park in! Easy to find and easy to check in!"
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
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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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. Oakland is known for its wineries and restaurants. Make sure you have time to check out the parks while you're in the area.

What are some of the best holiday rentals that Oakland has to offer?


~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
: This holiday home rental outside of Oakland offers a selection of games, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Oakland?

With 3 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?

While exploring the area, visit family-friendly sights like Douglas County Museum of History and Natural History, or get outside and enjoy nature at Umpqua River. MarshAnne Landing and Misty Oaks Vineyard 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 offer amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.