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Oakland Holiday Rentals

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Holiday Rentals in Oakland

2 bedrooms, desk, iron/ironing board, travel cot
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
9.8 out of 10, Exceptional, (52)
"We had a lovely stay in this cool, vintage decorated Roseburg house! We were in town for a livestock show for our 13 and 14 year old kiddos were showing sheep. They really loved the record player and the cool games that were provided in the living room. We loved this house because it was very much geared towards family. The decor was really cool and it was very cozy."
The price is NZ$360
per night
2 Jun - 3 Jun
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Exterior
Heavenly Bungalow, Entire Home!
10.0 out of 10, Exceptional, (21)
"Lovely, cozy home"
Heavenly Bungalow, Entire Home!
Smart TV
Lake View House
9.8 out of 10, Exceptional, (19)
"The view is breathtaking and the owners are so helpful and accommodating. Plenty of room for large groups."
Lake View House
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Property grounds
Quiet Riverfront Home! 5 Mins from Dorena Lake!
10.0 out of 10, Exceptional, (12)
"This is indeed a nice, quiet riverfront home. It's about 20 minutes from Cottage Grove, and the drive there is gorgeous. Great internet speed, so you shouldn't have any cellphone issues if you have wifi calling enabled on your phone. It has all the amenities that you'd need for a longer-term stay: full kitchen, full laundry, full bathroom. The Lee family are incredibly kind and personable,and I'd highly recommend this property to couples, small families, or anyone that just wants some peace and...
Quiet Riverfront Home! 5 Mins from Dorena Lake!
Property grounds
A Restful Studio Near a Creek and Forest - Pets
10.0 out of 10, Exceptional, (10)
"Wow, this was one of our most favorite stays anywhere! The studio was beautiful, so clean and lovely with everything we needed. Our dog was quite happy too! We really enjoyed the view from the deck of the meadow and tree covered hillside, plus the sound of the creek and of birds chirping. Great location-very convenient to Roseberg and hiking trails nearby. We most definitely will return! Although we never met in person, Ashley was awesome - very responsive, welcoming and accommodating!"
The price is NZ$320
per night
14 Jun - 15 Jun
A Restful Studio Near a Creek and Forest - Pets
Fridge, microwave, oven, stovetop
Home Sweet Home
5.6 out of 10, (8)
"Full kitchen. Everything was very clean. Mattresses were low quality but everything else was nice. Easy communication with Jimmy"
The price is NZ$333
per night
29 May - 30 May
Home Sweet Home
Property grounds
Below the Falls Lodge - Next to Golden & Silver Falls
9.8 out of 10, Exceptional, (184)
"Couldn’t have been more impressed! Absolutely loved the house and everything it has to offer. Having everything thing we needed while being away from the public was a dream. My children and dog absolutely loved the creek and being able to enjoy the forest while us adults enjoyed the break from technology and being able to slow down a bit. Can’t wait to return!"
Below the Falls Lodge - Next to Golden & Silver Falls
Property grounds
The Bucket List Retreat
9.6 out of 10, Exceptional, (24)
"Comfy beds, great location to our activity, accommodating owner who went out of their way to send us something we left behind. Would definitely stay a this property again."
The Bucket List Retreat
Living area
3 Bedroom House w/Game Room/Pets
10.0 out of 10, Exceptional, (2)
"We had a great time staying in Roseburg for my 30th birthday & celebrating Mother’s Day. Twenty minutes from Wild Life Safari, and close to the vineyards! My favorite part was game night at the house."
The price is NZ$810
per night
30 May - 31 May
3 Bedroom House w/Game Room/Pets
Fridge, microwave, stovetop, dishwasher
Family-Friendly Winston Vacation Rental w/ Deck!
10.0 out of 10, Exceptional, (5)
"The property is very nice with a good view. Very well supplied with all necessary items for cooking and meals. Ease of working with hostess."
Family-Friendly Winston Vacation Rental w/ Deck!
Fridge, microwave, oven, stovetop
Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg
9.6 out of 10, Exceptional, (10)
"Amazing stay. Great location. Very peaceful and a beautiful house! We enjoyed every part of it."
Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg
TV, table football, stereo
Lost World Lodge - Your Jurassic Park Vacation Rental
9.0 out of 10, Wonderful, (2)
"Loved the Lost World theme of the apartment. It was super clean, spacious, and great location. The KOA park is the cleanest park I've seen and we love the drive in movie theater."
Lost World Lodge - Your Jurassic Park Vacation Rental
Private kitchen
Charming Historical lodge across from Umpqua river
9.4 out of 10, Exceptional, (19)
"A wonderful place to stay highly recommended, and will go there again when we visit Glide."
The price is NZ$239
per night
29 May - 30 May
Charming Historical lodge across from Umpqua river
Fridge, microwave, oven, stovetop
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews
10.0 out of 10, Exceptional, (7)
"This is a wonderful little house in picture cottage Grove. The location was very close to Main Street where there are restaurants and shops. The house was very nicely decorated, the beds were comfortable, and the house had anything you would find in your own house (maybe even more!) Everything was well labeled so it was easy to find things. Would definitely stay here again."
The price is NZ$615
per night
29 May - 30 May
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews
Private kitchen
Historic Lodge across the street from the Umpqua River
9.8 out of 10, Exceptional, (18)
"The lodge owner JoAnne came to meet us as we pulled up in our truck. She gave a quick tour of the facility and our room. Very welcoming of our small dog, Bill. Invited us to a potluck on site that evening. There was an awesome musical trio of JoAnne’s friends. They played folk and rock tunes from the 60’s, 70’s and 80’s until about 9 pm. Very cool! Room and our restroom very clean. Bed very comfy. Best of all a fresh loaf of banana bread awaited us in our room. Very cool!"
The price is NZ$239
per night
29 May - 30 May
Historic Lodge across the street from the Umpqua River
Private kitchen
Indigo Collective - Modern Home
10.0 out of 10, Exceptional, (2)
"We loved staying here! Beautifully decorated and very comfortable! Beds were super comfortable - although 1 in the double queen room is very, very soft. Kitchen is well appointed - plenty of pans and cooking ware. Bathrooms were stocked - included shampoos, conditioner and soaps. As well as tons of towels, which was appreciated! Hot water is very hot, which was great but be warned if you have littles - could be too much for them. Will absolutely stay here again! Lovely!"
Indigo Collective - Modern Home
Beach
Beautiful RiverFront Home on the Umpqua River W/Private Dock & World Class Fishing
9.8 out of 10, Exceptional, (51)
"Pros: Great location on the river, beautiful surroundings Kitchens had all that was needed. Plenty of plates, utensils and cooking items. Showers were very satisfying, and the beds were comfortable. Lots of parking space. Had fun fishing from the dock. Cons: We were disappointed in the floors as they were not very clean. The entry doors were covered with stains, should be cleaned. We found some trash items from previous renters. Kitchen faucet leaked badly, spilling water onto the floor."
Beautiful RiverFront Home on the Umpqua River W/Private Dock & World Class Fishing
Exterior
Relaxing and peaceful cottage in rural area
10.0 out of 10, Exceptional, (2)
"The place was everything it advertised and more. Plenty of amenities to make your stay comfortable and a home away from home. Great location between I-5 and the coast. The hosts communication on how to get there was spot on, so it was easy to find. Thank you Melissa, I will be back!"
The price is NZ$386
per night
29 May - 30 May
Relaxing and peaceful cottage in rural area
Property grounds
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
9.8 out of 10, Exceptional, (16)
"Nice"
The price is NZ$372
per night
30 May - 31 May
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Interior
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
9.4 out of 10, Exceptional, (10)
"Great little home. The only complaint, the heater didn't really get the place warm."
The price is NZ$283
per night
24 Jun - 25 Jun
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
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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.

Other types of properties in Oakland you may be interested in

Terrace/patio
Rice Hill Inn
2.0 star property
7.4 out of 10, Good, (169)
"Nice clean room. Good location. Bed was comfortable. Bring your own pillows. "
The price is NZ$141
per night
29 May - 30 May
Rice Hill Inn
Property grounds
Five Bedroom Farmhouse Vineyard And Winery
10.0 out of 10, Exceptional, (1)
"The house slept 16 & was very spacious & gorgeous!! We had a wonderful time."
Five Bedroom Farmhouse Vineyard And Winery
BBQ/picnic area
Riverfront Inn Roseburg
2.0 star property
8.6 out of 10, Excellent, (1090)
"Great little hotel!"
The price is NZ$208
per night
29 May - 30 May
Riverfront Inn Roseburg
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oakland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oakland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oakland. Seeing all the best attractions is bound to make you fall in love with Oakland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oakland short-term rentals, that won’t be hard to do.

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’s there to see and do in Oakland?

Umpqua River and Oakland City Park are a couple of lovely local spots to get outside and enjoy nature. 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.

Recent reviews of Oakland properties
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