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Holiday Rentals in Oakland

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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!

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 loved this house! The little extras made all the difference! It was spotless, toiletries were stocked in the bathrooms, the kitchen was gorgeous and easy to cook in and our teens were beyond thrilled with all the snacks. It was the perfect place for a couple lazy days after Christmas. The hot tub was wonderful (including the big fluffy towels) and it was only a couple block walk to the cute little downtown area. We fully enjoyed our stay. The hosts were responsive and kind about any questions...
Two Story Victorian Farm House. Hot Tub!

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

9.8 out of 10, Exceptional, (88)
"It was wonderful to go back in time, furniture, turn table all brought back delightful memories of my childhood. Thanks for sharing your place with us. "
The price is €192
includes taxes & fees
19 Oct - 20 Oct
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

9.6 out of 10, Exceptional, (49)
"Bill's house was comfortable, and the house and property were consistent with the listing. The house and furnishings worked well for my family for our one-night stay."
The price is €204
includes taxes & fees
13 Oct - 14 Oct
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

Home Sweet Home

9.6 out of 10, Exceptional, (5)
"Truly enjoyed staying at "Home Sweet Home". Beds are very comfortable, home was very clean, hosts were quick to respond and give info through texts. Would definitely recommend staying here. Looking for a great place to stay while check out the wineries? You found the place."
The price is €197
includes taxes & fees
21 Oct - 22 Oct
Home Sweet Home

Below the Falls Lodge - Next to Golden & Silver Falls

9.8 out of 10, Exceptional, (198)
"Such a beautiful place to stay with lots to do! We went in the creek multiple times, sauna, hammock, and hiked the falls. I can tell how much love they put into this place because there is artistry put into every detail. A true hidden gem in the woods."
Below the Falls Lodge - Next to Golden & Silver Falls

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (34)
"Nice place, great location."
The price is €190
includes taxes & fees
16 Oct - 17 Oct
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (46)
"This house is great for a family trip to the Wildlife Safari! The location is perfect and the property is suited to accommodate all ages with plenty of room to spread out. Family games, a place to grill, large kitchen and attention to detail from the cleaning team. "
The price is €367
includes taxes & fees
11 Nov - 12 Nov
The Watusi Place - A Modern Umpqua Valley Getaway

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.4 out of 10, Exceptional, (19)
"Just the right size and location for a wine country getaway weekend. Had everything we needed, and more. Will not hesitate to book again next trip, if it's available."
The price is €154
includes taxes & fees
15 Oct - 16 Oct
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

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

9.4 out of 10, Exceptional, (23)
"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

Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg

9.6 out of 10, Exceptional, (29)
"Awesome place to stay and great hosts. Very Responsive. Nice and clean, everything was as described. Highly Recommend staying here if you have the chance! "
Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg

The Cottage at Wild Goose Outpost

2.0 star property
9.4 out of 10, Exceptional, (3)
"The kitchen was really nice, and the house was very comfortable. "
The price is €215
includes taxes & fees
13 Oct - 14 Oct
The Cottage at Wild Goose Outpost

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

9.6 out of 10, Exceptional, (224)
"We had a wonderful get together. The house was perfect for us and the location is fantastic. Right by the river. "
The price is €353
includes taxes & fees
7 Nov - 8 Nov
Great Vintage 2500sq ft. country cabin amazing river front setting!

River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water

9.8 out of 10, Exceptional, (57)
"Amazing!"
River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

9.4 out of 10, Exceptional, (13)
"great property"
The price is €398
includes taxes & fees
13 Oct - 14 Oct
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Family home

9.8 out of 10, Exceptional, (6)
"I would suggest to everyone to stay here!"
Family home

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (63)
"Wonderful property,had everything we needed,Thankyou again"
Firewater Lodge Cabin Experience

Red Tiny Twins, Downtown Eco & Pet Friendly Stay

9.8 out of 10, Exceptional, (18)
"Enjoyed the accommodations. just as advertised would stay again."
The price is €154
includes taxes & fees
13 Oct - 14 Oct
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
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, 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 €154 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. 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?

Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun: This holiday home rental outside of Oakland offers a fireplace, a patio 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 can relax into your holiday with a garden and a selection of games.

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.