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Holiday Rentals in Oakland

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Holiday Rentals in Oakland

Southern Oregon Cabin: Fire Pit & Private Pond!

2.0 star property
10.0 out of 10, Exceptional, (2)
"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!

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!

10.0 out of 10, Exceptional, (2)
Romantic Vineyard Getaway in Oakland: Mtn Views!

Romantic Vineyard Getaway in Oakland: Mtn Views!

3.0 star property
Romantic Vineyard Getaway in Oakland: Mtn Views!

Vineyard Farmhouse in Oakland w/ Hot Tub!

10.0 out of 10, Exceptional, (2)
"The property setting is absolutely gorgeous and serene. It is 16 minutes to downtown Roseburg with easy freeway access. The home is spacious and beautifully appointed. We had three families meet up for a wedding, and there was amble room to retire or to gather together. Expansive back decks with well maintained hot tub was the cout de taut!"
Vineyard Farmhouse in Oakland w/ Hot Tub!

Vineyard Farmhouse in Oakland w/ Hot Tub!

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

Two Story Victorian Farm House. Hot Tub!

10.0 out of 10, Exceptional, (6)
"We had an amazing time! The house is clean and spacious. Fully stocked, comfy beds and great location. We will be back for sure!"
Two Story Victorian Farm House. Hot Tub!

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

9.4 out of 10, Exceptional, (212)
"Private, views are incredible and perfectly situated. "
Great Vintage 2500sq ft. country cabin amazing river front setting!

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

The price is €438
includes taxes & fees
13 Apr - 14 Apr
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (36)
"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 €287
includes taxes & fees
30 Apr - 1 May
The Watusi Place - A Modern Umpqua Valley Getaway

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (31)
"Such an amazing property and the house is absolutely perfect! The attention to detail is on point. If I could live here, I would. A perfect quiet retreat just miutes from Roseburg. Will definitely book again! "
The price is €150
includes taxes & fees
11 May - 12 May
A Restful Studio Near a Creek and Forest - Pets

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

9.8 out of 10, Exceptional, (15)
"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 €289
includes taxes & fees
11 May - 12 May
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews

Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.

9.4 out of 10, Exceptional, (8)
"Beautiful, quiet, comfortable, clean. 5 stars"
Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.

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

9.8 out of 10, Exceptional, (24)
"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. "
The price is €254
includes taxes & fees
15 Apr - 16 Apr
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

Family-Friendly Winston Vacation Rental w/ Deck!

10.0 out of 10, Exceptional, (12)
"Very nice place. They have thought of everything. Thanks "
Family-Friendly Winston Vacation Rental w/ Deck!

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

9.8 out of 10, Exceptional, (72)
"We chose this property because our adult child lives in Roseburg with their partner. We came to hang out and help them work on their house for about a week. It was always so nice to come back to this beauty and relax. We weren’t able to enjoy the beautiful outdoor amenities, but I look forward to the next time we stay hanging out on the back porch and using the grill and the fire pit. The beds were comfy. Everything was very clean. We had all that we needed. I highly recommend this rental. "
The price is €192
includes taxes & fees
12 May - 13 May
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

Tiny House nestled into the Forest on 160 acre Playground.

8.6 out of 10, Excellent, (4)
"Cute tiny house on an absolutely lovely, serene forested hillside. Really close to town, all things considered - about 20 minutes from the hospital where I was working for the month! The one downside that is only an issue with more extended stays like mine - the compost toilet did get a tad smelly as the weeks went by. Not to an unbearable degree but just a small caveat to the five stars! "
The price is €154
includes taxes & fees
22 Apr - 23 Apr
Tiny House nestled into the Forest on 160 acre Playground.

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (53)
"Had a wonderful time and wished we could stay longer."
Firewater Lodge Cabin Experience

Below the Falls Lodge - Next to Golden & Silver Falls

9.8 out of 10, Exceptional, (191)
"This was such a relaxing 2 days! The home is fully stocked with blankets, towels, cleaning, kitchen has NICE cookware, real plates utensils, silverware etc. Most common condiments are in frig and sugar flower etc under cupboard. Nice to light a fire, it was my first and great instructions with supplies all that is needed is there but paper products packaging plates and bags are great to help start the fire. There was no cell service, no internet but that is temporary. I liked that technology was...
Below the Falls Lodge - Next to Golden & Silver Falls

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

9.6 out of 10, Exceptional, (55)
"We had a wonderful stay. With the number of bedrooms and bathrooms, it was perfect for our group size. The host was great and very responsive when needed. The game room provided a fun time for every one of all ages. With the folding tables and chairs located on site, it provided the perfect amount of seating for our group for our Thanksgiving meal. Would definitely recommend this place and hope to rent it again in the future."
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
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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Other types of properties in Oakland you may be interested in

The Ranch Motel by OYO Oakland I-5

2.0 star property
9.0 out of 10, Wonderful, (56)
"Although it is of course a bit dated, the staff is friendly and accommodating. Overall a pleasant stay."
The price is €83
includes taxes & fees
18 Apr - 19 Apr
The Ranch Motel by OYO Oakland I-5

Rice Hill Inn

2.0 star property
7.6 out of 10, Good, (199)
"Could use an update. New paint, flooring, matttresses."
The price is €72
includes taxes & fees
11 May - 12 May
Rice Hill Inn

Southern Oregon Cabin: Fire Pit & Private Pond!

2.0 star property
10.0 out of 10, Exceptional, (2)
"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!
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.

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?

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool: This holiday home rental outside of Oakland offers a fireplace, 1 hot tub and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.