Lodging Image

Oakland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Oakland vacation rentals

Terrace/patio

1. Lil Cedar Lodge

Lil Cedar Lodge
Roseburg
10.0 out of 10, Exceptional, (2 reviews)
"Awesome place. Really enjoyed my stay."
United States
Zakary S.
The price is AED 314
AED 412 total
includes taxes & fees
6 Aug - 7 Aug
Lil Cedar Lodge
Exterior

2. Tiny House nestled into the Forest on 160 acre Playground.

Tiny House nestled into the Forest on 160 acre Playground.
Roseburg
9.8 out of 10, Exceptional, (17 reviews)
"Great location, nice and quiet easy to get to fantastic hosts."
United States
Lee and Kristy D.
The price is AED 397
AED 514 total
includes taxes & fees
10 Aug - 11 Aug
Tiny House nestled into the Forest on 160 acre Playground.
Terrace/patio

3. Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Roseburg
10.0 out of 10, Exceptional, (25 reviews)
"Beautiful property and incredible stay. Not only was the room clean, private and super comfortable, the hosts were amazing. They made my comfort a priority every day! Definitely would give it a 5 star rating, I will recommend it to family and friends."
United States
Betty W.
The price is AED 907
AED 1,138 total
includes taxes & fees
6 Aug - 7 Aug
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Exterior

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

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Roseburg
9.8 out of 10, Exceptional, (111 reviews)
"We really enjoyed our stay at April’s house. It was a comfortable house and we loved being so close to Stewart Park for our daily walks."
United States
Sara W.
The price is AED 441
AED 776 total
includes taxes & fees
10 Aug - 11 Aug
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Deluxe Apartment, City View | Private kitchen

5. Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
The price is AED 1,032
AED 1,412 total
includes taxes & fees
13 Aug - 14 Aug
Bell Sister Flats
Dining

6. Private Umpqua River Retreat w/ 2 King Suites & Patio

Private Umpqua River Retreat w/ 2 King Suites & Patio
Roseburg
10.0 out of 10, Exceptional, (2 reviews)
"Great property with wonderful views and a quiet relaxing back patio. Large kitchen with a good refrigerator. Very comfortable beds."
United States
Laura O.
Private Umpqua River Retreat w/ 2 King Suites & Patio
Exterior detail

7. Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.6 out of 10, Exceptional, (21 reviews)
"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 AED 331
AED 644 total
includes taxes & fees
15 Aug - 16 Aug
Downtown Stay at the Blue Tiny Twin
Dining

8. 4 BEDROOM House across from River in Best Roseburg area!

4 BEDROOM House across from River in Best Roseburg area!
Roseburg
10.0 out of 10, Exceptional, (30 reviews)
"Great stay as always"
United States
Anonymous traveler
The price is AED 459
AED 942 total
includes taxes & fees
24 Aug - 25 Aug
4 BEDROOM House across from River in Best Roseburg area!
Exterior detail

9. Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Roseburg
9.6 out of 10, Exceptional, (30 reviews)
"Finding the entry to the property was hardest part. Parking was OK. The views and the space was great. Nice central location for many places to visit."
United States
Nicole B.
The price is AED 404
AED 732 total
includes taxes & fees
23 Aug - 24 Aug
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Exterior

10. The Urban Boho Charmer with Private Backyard, BBQ & Hammock

The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Roseburg
9.6 out of 10, Exceptional, (42 reviews)
"Nice place, great location."
United States
Gordon
The price is AED 459
AED 849 total
includes taxes & fees
19 Aug - 20 Aug
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Exterior

11. Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (26 reviews)
"It was a perfect place for us to stay for a short trip to visit family with our two little dogs."
United States
Rochelle S.
The price is AED 298
AED 607 total
includes taxes & fees
9 Aug - 10 Aug
Downtown Stay at the Red Tiny Twin!
Coffee/tea maker, fridge, microwave, oven

12. Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
10.0 out of 10, Exceptional, (3 reviews)
"Bell Sister Flats is amazing - so gorgeous, warm and inviting. We loved being on Main Street and walking to coffee, dinner, drinks. So much attention to detail and such comfort provided from the bed to the sheets to the towels and love seat and, oh the shower! Terry and Paul were wonderful hosts, so attentive and generous. Loved that they promoted the local community with goods and services in the flat. Loved our stay!"
United States
Tara T.
The price is AED 804
AED 1,323 total
includes taxes & fees
13 Aug - 14 Aug
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Dining

13. The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (57 reviews)
"Good hosts & very nice home."
United States
Pamela M.
The price is AED 595
AED 1,423 total
includes taxes & fees
11 Aug - 12 Aug
The Watusi Place - A Modern Umpqua Valley Getaway
Exterior detail

14. Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
The price is AED 878
AED 1,420 total
includes taxes & fees
4 Sep - 5 Sep
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Coffee/tea maker, fridge, microwave, oven

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

Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews
Cottage Grove
9.6 out of 10, Exceptional, (33 reviews)
"Great little house. Had everything you needed. About a 20 min drive south of Eugene. Would book again if the need arose."
United States
Kevin
The price is AED 645
AED 1,262 total
includes taxes & fees
31 Aug - 1 Sep
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews
Property grounds

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

Great Vintage 2500sq ft. country cabin amazing river front setting!
Scottsburg
9.6 out of 10, Exceptional, (234 reviews)
"Great space — great for a large group!"
United States
Corey N.
The price is AED 922
AED 1,775 total
includes taxes & fees
1 Sep - 2 Sep
Great Vintage 2500sq ft. country cabin amazing river front setting!
Interior

17. Below the Falls Lodge - Next to Golden & Silver Falls

Below the Falls Lodge - Next to Golden & Silver Falls
Coos Bay
9.8 out of 10, Exceptional, (212 reviews)
"The location is spectacular "
United States
John S.
The price is AED 1,010
AED 1,473 total
includes taxes & fees
2 Sep - 3 Sep
Below the Falls Lodge - Next to Golden & Silver Falls
Private kitchen

18. The Little Pearl, Boutique Designer Cottage in Cottage Grove’s Historic District

The Little Pearl, Boutique Designer Cottage in Cottage Grove’s Historic District
Cottage Grove
The price is AED 807
AED 1,486 total
includes taxes & fees
1 Sep - 2 Sep
The Little Pearl, Boutique Designer Cottage in Cottage Grove’s Historic District
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oakland Hotel Reviews

Riverfront Inn Roseburg

Riverfront Inn Roseburg

10/10 Excellent
"Loved the balcony off the back with view of river. Great place to stop for the night (we were traveling through). Several places to eat within walking distance."
Jennifer 1-night trip
Posted less than an hour ago
Riverfront Inn Roseburg

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?

Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews: This vacation home rental near Oakland is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Oakland?

With 5 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. In the larger area, you’ll find MarshAnne Landing and Reustle Prayer Rock Vineyards.

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.