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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!

Southern Oregon Cabin: Fire Pit & Private Pond!

2.0 star property
9.6 out of 10, Exceptional, (4)
"Great little place to stay, outside amenities were great! This is a smaller tiny home, so not much room for more than 2 adults inside. "
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!

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!

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, (82)
"Love this little abode and recommend "
The price is €190
includes taxes & fees
31 Aug - 1 Sept
<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, (219)
"Private, views are incredible and perfectly situated. "
The price is €443
includes taxes & fees
28 Aug - 29 Aug
Great Vintage 2500sq ft. country cabin amazing river front setting!

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

9.8 out of 10, Exceptional, (23)
"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 €279
includes taxes & fees
8 Sept - 9 Sept
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews

Home Sweet Home

10.0 out of 10, Exceptional, (2)
"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."
Home Sweet Home

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (28)
"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 price is €191
includes taxes & fees
18 Aug - 19 Aug
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

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

10.0 out of 10, Exceptional, (43)
"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 €181
includes taxes & fees
1 Sept - 2 Sept
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (41)
"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 €343
includes taxes & fees
19 Aug - 20 Aug
The Watusi Place - A Modern Umpqua Valley Getaway

Below the Falls Lodge - Next to Golden & Silver Falls

9.8 out of 10, Exceptional, (195)
"So peaceful. I would stay here again in a heartbeat. I wouldn’t change a thing. Worth the time to go see the falls. "
Below the Falls Lodge - Next to Golden & Silver Falls

Tiny House nestled into the Forest on 160 acre Playground.

9.4 out of 10, Exceptional, (9)
"It was such a nice little spot to get away."
The price is €139
includes taxes & fees
14 Aug - 15 Aug
Tiny House nestled into the Forest on 160 acre Playground.

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (61)
"This place was amazing and we will be going back for sure. Peaceful and relaxing setting. Home is beautiful and has everything you will need. "
Firewater Lodge Cabin Experience

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

9.8 out of 10, Exceptional, (54)
"House has the most amazing views. Perfect location for hiking all of the waterfalls. We would most definitely stay again!"
River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water

River Vista Vacation Homes

3.0 star property
9.2 out of 10, Wonderful, (45)
"What a magical place. Just what this busy mom of 3 needed to clear my mind and relax for a couple of days. I wish I could stay longer! I will be back "
River Vista Vacation Homes

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. "
The price is €290
includes taxes & fees
18 Aug - 19 Aug
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
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

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.