Holiday houses in Winston

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Popular amenities for Winston holiday rentals

Stay near Winston's top sights

Wildlife Safari61 locals recommend
Abacela Winery24 locals recommend
Carlos5 locals recommend

Other great holiday rentals in Winston

Top Guest favourite
Cabin in Umpqua
4.99 out of 5 average rating, 254 reviews

Rustic Riverfront Cabin

GlenRating, 5 stars2 days ago
The cabin was everting that we hoped that it would be, and more! The location is so peaceful and relaxing and the cabin itself was so clean and comfortable. They have all the "little things" that make a stay enjoyable and don't skimp on the ammenties. Response time for our communications with Cheri and Cassia was very quick a accomodating. We look forward to returing to this property!
Top Guest favourite
Home in Merlin
5 out of 5 average rating, 146 reviews

Alder Creek retreat

IlseRating, 5 stars2 days ago
Thank you very much for our stay in your beautiful home. It was great that all necessities were available to us and we really enjoyed our stay. The fireplace in the living room was a treat! The large back garden and quiet atmosphere were also fantastic. An extra benefit was the fantastic responsiveness of the host which we really appreciated when we had questions thanks again and hope to see you soon.
Superhost
Home in Umpqua
4.9 out of 5 average rating, 21 reviews

Home with cabin effect- private access to river

StephanieRating, 5 stars4 months ago
We really enjoyed our stay. Deep bath tub and amazing hottub for hard working individuals that need relaxation on their vacation. We spent Christmas here and it was probably the best Christmas we've ever had just playing board games and spending time together. I highly recommend this place and hope to return in the future.
Superhost
Townhouse in Myrtle Creek
4.78 out of 5 average rating, 41 reviews

The Sojourners Stop in the heart of Myrtle Creek

KellyRating, 5 stars4 months ago
Thank you Mike for the convenient location and clean space!
Top Guest favourite
Farm stay in Oakland
4.95 out of 5 average rating, 40 reviews

Cozy home on Christmas tree farm off of I-5

ChandraRating, 5 stars1 month ago
Wow! Gorgeous landscaping and views of the valley, river and hills. And rolling fields of baby Christmas trees! Even on a gray, soggy weekend it was lovely. Would be a great spot for a wedding. Guest house is way more spacious than expected and we were greeted by a warm, hand written note and cheery pellet-stove fire. Just enough seasonal decor sprinkled about to make it feel like we were visiting a much-loved home. The bed was super-comfy and access into and throughout the house was easy for mobility-challenged guests. Communication with the hosts was great. Can't wait to come back!
Guest favourite
Home in Grants Pass
4.97 out of 5 average rating, 296 reviews

Private Carriage House

DerekRating, 5 stars1 month ago
Ed and Jacquie’s place was exactly what we needed. We were on a road trip moving some stuff and towing a trailer, so finding a private, safe spot where we didn’t have to unload everything was a big deal. Their property was perfect, and the pull-through driveway made it super easy to get in and out with the trailer. On top of that, Ed and Jacquie were incredibly kind and welcoming. Honestly, some of the nicest hosts we’ve ever had. The property was peaceful and relaxing, with a creek out back, and the house itself was cozy and comfortable. We felt right at home. I only wish we could have stayed longer! If you’re in the area and need somewhere to stay, definitely stay here. We’d come back in a heartbeat.
Guest favourite
Guesthouse in Roseburg
5 out of 5 average rating, 7 reviews

Guest Cottage in Umpqua Valley Wine Country

TyraRating, 5 stars9 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
Cabin in Eagle Point
4.96 out of 5 average rating, 26 reviews

Private Ranch Log Cabin Lakeside Escape

ShannonRating, 5 stars1 month ago
What a incredible experience! My fiance and I came here to celebrate our anniversary and we are so happy that we did. The cabin was gorgeous(inside and out). It has all the modern amenities your heart could desire while still also holding that traditional cabin feel. It was very cozy and had very beautiful art work and artifacts through out. The kitchen is stocked with organic products(we appreciate that so much!!). We were also greeted with a lovely welcome basket that was stuffed full of different snacks , a very good bottle of wine and quail eggs. The view from the cabin of the lake and valley was gorgeous. We really enjoyed taking the row boat out on the lake and fishing, it was great having an entire lake to ourselves. We enjoyed walking around the lake and looking at all the cool rocks(agates, etc). There is so much to do here, we wish we would have more time to explore more of the property. Truly natures paradise. There is something for everyone here!

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