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Oakland Vacation Rentals

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Vacation 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."
United States
Wayne
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! "
United States
Elizabeth
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...
United States
Shannon H.
Two Story Victorian Farm House. Hot Tub!
Below the Falls Lodge - Next to Golden & Silver Falls
9.8 out of 10, Exceptional, (199)
"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."
United States
Wendy M.
Below the Falls Lodge - Next to Golden & Silver Falls
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
9.6 out of 10, Exceptional, (50)
"It was a great place, super close proximity to grocery stores and the airport which is where I needed to be each day for work. "
United States
Dana M.
$181 nightly
The price is $198
Oct 29 - Oct 30
Total with taxes and fees
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
<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. "
United States
Diane
$198 nightly
The price is $217
Oct 31 - Nov 1
Total with taxes and fees
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Firewater Lodge Cabin Experience
10.0 out of 10, Exceptional, (63)
"The cabin was better than expected and I loved the privacy, peace and quiet of the property and surroundings. We had a very enjoyable stay. "
United States
Foster G.
Firewater Lodge Cabin Experience
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
9.6 out of 10, Exceptional, (36)
"Nice place, great location."
United States
Gordon
$196 nightly
The price is $215
Oct 30 - Oct 31
Total with taxes and fees
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Home Sweet Home
9.8 out of 10, Exceptional, (7)
"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."
United States
Kristi S.
$203 nightly
The price is $222
Oct 31 - Nov 1
Total with taxes and fees
Home Sweet Home
Great Vintage 2500sq ft. country cabin amazing river front setting!
9.6 out of 10, Exceptional, (226)
"We had a wonderful get together. The house was perfect for us and the location is fantastic. Right by the river. "
United States
Geoff B.
$359 nightly
The price is $364
Oct 29 - Oct 30
Total with taxes and fees
Great Vintage 2500sq ft. country cabin amazing river front setting!
Tiny House nestled into the Forest on 160 acre Playground.
9.6 out of 10, Exceptional, (11)
"Just as described, clean & comfortable loft bed. Owner great with communication & so nice. Would stay again "
United States
Lucinda H.
$155 nightly
The price is $158
Oct 29 - Oct 30
Total with taxes and fees
Tiny House nestled into the Forest on 160 acre Playground.
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
9.4 out of 10, Exceptional, (13)
"great property"
United States
Mai
$444 nightly
The price is $451
Nov 2 - Nov 3
Total with taxes and fees
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
9.8 out of 10, Exceptional, (36)
"This place is great. We have stayed multiple times. Will continue to come back here when in the area. "
United States
Benjamin B.
$264 nightly
The price is $289
Oct 30 - Oct 31
Total with taxes and fees
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
The Watusi Place - A Modern Umpqua Valley Getaway
10.0 out of 10, Exceptional, (46)
"The house was amazing! Easy to get in, clean and well stocked. Definitely recommend to anyone looking for a nice place."
United States
Amy H.
$388 nightly
The price is $421
Nov 11 - Nov 12
Total with taxes and fees
The Watusi Place - A Modern Umpqua Valley Getaway
Family home
9.8 out of 10, Exceptional, (7)
"I would suggest to everyone to stay here!"
United States
Kendal M.
Family home
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! "
United States
Daniel S.
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. "
United States
Bayley F.
$243 nightly
The price is $247
Oct 29 - Oct 30
Total with taxes and fees
The Cottage at Wild Goose Outpost
20' yurt on private property
9.6 out of 10, Exceptional, (14)
"Pleasant Stay! Only comment is from the showers you can see there bathrooms from above. But otherwise so cute and quiet, we enjoyed our stay ❤️ plus there is A/C! "
United States
Brooklyn
20' yurt on private property
River Vista Vacation Homes
3.0 star property
9.2 out of 10, Wonderful, (45)
"The place was right on the river which was beautiful and it had everything that we would need. It was clean and pretty roomy for my family and I to spend the weekend there and we absolutely loved it! We’re already trying to make another trip out here!"
United States
Emily
River Vista Vacation Homes
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 vacation rentals

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

Oakland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oakland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $158 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland vacation 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 vacation.

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 vacation rentals in Oakland?

Yes, we offer vacation rentals close to top sights in Oakland, or you can choose a secluded option if you'd like a relaxing place to 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's the top vacation rental in Oakland?

Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital: This vacation home rental near Oakland is located on a river and offers a garden, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Oakland?

With 3 Expedia vacation rentals, you're sure 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 vacation rental in Oakland like?

Vacation rentals are private properties you can stay in for short or long periods in Oakland. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.