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Oakland Holiday Rentals

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Holiday Rentals in Oakland

the Bunkhouse coyote- Private Studio Retreat Room
2.0 star property
10.0 out of 10, Exceptional, (1)
"The views are out of this world! The horses on property are gorgeous! This truly felt like a vacation within a vacation (drove that way for the wildlife safari park). We plan to come back again! Property owner is a sweetheart! "
United States
Charles B.
The price is AU$185
includes taxes & fees
30 Oct - 31 Oct
the Bunkhouse coyote- Private Studio Retreat Room
Hot Tub & Fenced Yard: Cozy Cottage Grove Home
3.0 star property
The price is AU$574
includes taxes & fees
22 Oct - 23 Oct
Hot Tub & Fenced Yard: Cozy Cottage Grove Home
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.
The price is AU$383
includes taxes & fees
24 Oct - 25 Oct
The Cottage at Wild Goose Outpost
Bunkhouse Bear Room -Private Studio Retreat
2.0 star property
The price is AU$182
includes taxes & fees
23 Oct - 24 Oct
Bunkhouse Bear Room -Private Studio Retreat
A Restful Studio Near a Creek and Forest - Pets
10.0 out of 10, Exceptional, (37)
"Peaceful and clean."
United States
Aiko V.
The price is AU$257
includes taxes & fees
26 Oct - 27 Oct
A Restful Studio Near a Creek and Forest - Pets
Lil Cedar Lodge
The price is AU$169
includes taxes & fees
29 Oct - 30 Oct
Lil Cedar Lodge
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
10.0 out of 10, Exceptional, (23)
"My parents stayed here for our son's graduation. They were very impressed with the hosts and warm welcome they received"
United States
SharonLee S.
The price is AU$275
includes taxes & fees
1 Nov - 2 Nov
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
<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
The price is AU$338
includes taxes & fees
24 Oct - 25 Oct
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
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.
The price is AU$245
includes taxes & fees
23 Oct - 24 Oct
Tiny House nestled into the Forest on 160 acre Playground.
Private bungalow with AC in charming Roseburg
2.0 star property
The price is AU$547
includes taxes & fees
29 Oct - 30 Oct
Private bungalow with AC in charming Roseburg
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."
United States
John L.
The price is AU$270
includes taxes & fees
30 Oct - 31 Oct
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
9.6 out of 10, Exceptional, (35)
"Nice place, great location."
United States
Gordon
The price is AU$338
includes taxes & fees
30 Oct - 31 Oct
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Bell Sister Flats
2.0 star property
The price is AU$699
includes taxes & fees
3 Nov - 4 Nov
Bell Sister Flats
Great Vintage 2500sq ft. country cabin amazing river front setting!
9.6 out of 10, Exceptional, (225)
"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.
The price is AU$566
includes taxes & fees
31 Oct - 1 Nov
Great Vintage 2500sq ft. country cabin amazing river front setting!
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."
United States
Kristi S.
The price is AU$345
includes taxes & fees
22 Oct - 23 Oct
Home Sweet Home
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
9.8 out of 10, Exceptional, (35)
"This place is great. We have stayed multiple times. Will continue to come back here when in the area. "
United States
Benjamin B.
The price is AU$451
includes taxes & fees
2 Nov - 3 Nov
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Lone Rock Guest House, 20 acres minutes from the North Umpqua River
2.0 star property
The price is AU$866
includes taxes & fees
15 Nov - 16 Nov
Lone Rock Guest House, 20 acres minutes from the North Umpqua River
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
2.0 star property
10.0 out of 10, Exceptional, (3)
"Terry's place was such a treat! The apartment exceeded so many of our expectations and was perfect for our mini vacation. Wonderful features and amenities. Beautiful finishes, linens and furnishings. Super responsive host. We look forward to our next stay!"
United States
CARISSA F.
The price is AU$654
includes taxes & fees
31 Oct - 1 Nov
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
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. "
United States
Ronauda G.
The price is AU$694
includes taxes & fees
14 Nov - 15 Nov
The Watusi Place - A Modern Umpqua Valley Getaway
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
9.4 out of 10, Exceptional, (13)
"great property"
United States
Mai
The price is AU$700
includes taxes & fees
26 Oct - 27 Oct
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
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, 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 favourite 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 depend 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 AU$270 per night. Entering your travel dates in the search wizard might find you 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?


~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.