
Holiday rentals in Oakland
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Top-rated holiday rentals in Oakland
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Oakland
Top guest favourite

Cabin in Roseburg
4.99 out of 5 average rating, 95 reviewsFirewater Lodge Log Cabin
MichelleRating, 5 stars2 weeks ago
This place is absolutely amazing!! everything you would need and so much more. so peaceful and quite. Beds are comfy to sleep in.
Guest favourite

Tiny home in Glide
4.96 out of 5 average rating, 69 reviewsLittle Cabin, scenic North Umpqua corridor
EveRating, 5 stars3 weeks ago
The tiny cabin was really fun. Everything has its place, even the super comfy chairs in the living space. I didn't really pay attention to the loft bed in the description but that's on me. It's a mattress in a loft that is quite low. The mattress was very comfortable but I was glad that I'm short as the ceiling is pretty low. The river outside the cabin was beautiful and we had dinner on the porch which really made the most of the space.
Top guest favourite

Tiny home in Drain
4.94 out of 5 average rating, 71 reviewsCountry Guest House - Leona Mills
PaigeRating, 5 stars1 week ago
We really enjoyed our stay! We were in town for a high school graduation and this property was perfect for a weekend getaway. The space was small but exactly as expected—clean, well-maintained, and thoughtfully set up. The property itself was beautiful with lots to explore and walk around. It felt peaceful and private, even though it was conveniently close to the freeway (without any noise issues). The host was very friendly and welcoming—we enjoyed chatting with him during our stay. Highly recommend!
Top guest favourite

Home in Roseburg
4.92 out of 5 average rating, 59 reviewsSequoia Cottage
TroyRating, 5 stars2 weeks ago
We rented this home for the guest speakers for the weekend. They commented that the place was "perfect" for what they needed. The house was very welcoming and made them feel right at home. Great hostess, great communication, and great place!
Guest favourite

Guest house in Roseburg
5 out of 5 average rating, 7 reviewsGuest Cottage in Umpqua Valley Wine Country
TyraRating, 5 stars11 months ago
Excellent quiet cottage outside of town a short drive. Was a perfect place to stay, wouldn't hesitate to book here again. Everything was as described and both check in and check out were simple and seamless.
Guest favourite

Home in Roseburg North
4.88 out of 5 average rating, 8 reviewsXenia House - North Roseburg
RosannaRating, 5 stars1 week ago
My Family and I were in town for 2025 Sheep Shearing Competition this place made us feel right at home. We traveled from California so the place was amazing. Alisha was so responsive and Helpful. I truly recommend place to everyone trying to stay. We hope to be back next year.
Guest favourite

Home in Glide
4.89 out of 5 average rating, 82 reviewsRaven's Rook River House 3 BR 1.5 Ba Sleeps 8
StevieRating, 5 stars2 weeks ago
The locale was idyllic, the host was gracious and on top of things, and everyone had a splendid time! We will be returning in the fall for sure!!
Superhost

Cabin in Roseburg
4.75 out of 5 average rating, 12 reviewsTuscan Cottage in the Orchard
DaniRating, 5 stars1 week ago
A great place to hang out in the front yard and have a fire. We loved the chickens, cats, deer, and other wild life we saw. The house itself is both cozy and functional. If you will be using the downstairs furniture to sleep versus the loft, would recommend bringing an eye mask since the curtains do not block a ton of light. It was a perfect space for a quick girls’ weekend, I would stay again.
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