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Vacation rentals in Winston

Vacation rentals in Winston

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Winston

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Riverside Wildlife Safari close retreat
    Entire house · 6 guests · 4 beds · 2 baths
    Riverside Wildlife Safari close retreat

    Park like setting, 2 decks front and back, 3 bedrooms and 2 full baths, TV with Dish, Air conditioning, vaulted ceilings, Master suite, laundry, picnic area, has circle parking, easy access path to the river, Barn out back has animals, BBQ available, fire pit,close to wineries, Wild life Safari only 2 miles away, restaurants within 2 miles, bicycle path to town.

    What guests are saying:

    “My grandfather lives in Roseburg and a group of relatives from out of state wanted to celebrate his 96th birthday. We rented this three bedroom home for my parents, my aunt, and I to be able to stay in one place and to have a home base to hang out with my grandfather. The home was clean and well set up. It is situated in a quiet, picturesque area near the Umpqua River. The bedrooms were perfect for the guests, and the living room was well suited for us to hang out and visit. The trickiest part of the home is finding it (especially in the dark) the first time. The wildlife decor made me want to go to Wildlife Safari and I wish we would have had more time.”

  • Downtown Roseburg 1921 Craftsman "Desert" Room
    SUPERHOSTPrivate room · 2 guests · 2 beds · 1 shared bath
    Downtown Roseburg 1921 Craftsman "Desert" Room

    Sanitized daily! Our 1921 Craftsman is two blocks from downtown restaurants, breweries, wineries, antique stores, and galleries. Easy access to I-5 and Route 138 to Crater Lake. The second floor is exclusively for our guests with a separate entry. There are two bedrooms--Ocean and Desert Rooms--listed separately. Bedrooms share the bathroom, kitchenette, and lounge area. The Desert Room has a twin beds. The back patio offers a beautiful view of the surrounding hills. Wifi and parking.

    What guests are saying:

    “Adorable little spot blocks away from down town. We stayed for one night and loved the amenities. We really enjoyed the common area where we spent hours looking over the world map and playing Monopoly. The Desert Room was deforest accordingly and had two single beds. As a married couple we typically sleep in the same bed, but for one night we managed. Loved having our pup with us and there were complimentary dog bags. Overall, we highly recommend this place.”

  • Quiet, relaxing bedroom & welcoming hosts
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bath
    Quiet, relaxing bedroom & welcoming hosts

    This is a bedroom/bath in a family home and would be especially ideal for the solo traveler or business person. It's a quiet area in a residential neighborhood and we are welcoming hosts. The bathroom would be only lightly used by us; we mostly don't use this bathroom because we have a second one. You're welcome to help yourself to coffee, tea and cereal in the morning. The bed is super comfortable, with a memory foam topper and there is a nice table to hold a suitcase or other items.

    What guests are saying:

    “First off, let me say that I usually don't stay in private rooms but usually prefer to have the entire place to myself when using this service. However, I had to make an emergency trip to help out my dad who has Parkinson's. So, with this in mind, I figured I would just rent out a room for a few days. I am so glad I did! Cindy and Bruce (and their lovable dog, Lucy) were the perfect hosts! They made my stay so easy. Cindy was quick to reply to my request and was super accommodating. Check in was easy. Cindy greeted me at the door, as well as Lucy. The location was perfect, as their home is located in a quiet and clean cul-de-sac. I really appreciated how easy going both Cindy and Bruce were. It was like I was home. As their home is located in a quiet cul-de-sac, sleeping at night was very restful. The room was also very restful. Very clean, spacious, and a comfortable bed. There was no issue with adjusting the temperature in the room, even as the weather was a little warm. I was still able to keep cool. There is a large TV with cable, though I didn't watch TV. Their wifi was strong (in other places I've stayed in the past, this sometimes had been an issue). Cindy and Bruce also were generous with the stuff they have in their kitchen. They have wonderful coffee, and Cindy even asked if I wanted breakfast. And if you have time, Bruce will be more than happy to show you his wonderful garden! I didn't have time to check it out, but I sure checked out their produce! Bruce is an amazing gardener! Even upon leaving, they made check-out super easy. I just needed to make sure to close the windows in my room, if I left them open. They take care of the rest! I can go on and on. But, I will say one last thing, if I am in Roseburg again in the future, I definitely would come back again, even if it means staying in a private room again. ;)”

Holiday rentals for every style

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Popular amenities for Winston holiday rentals

  • Kitchen
  • Wi-Fi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Winston

Riverside Wildlife Safari close retreat
Entire house
Riverside Wildlife Safari close retreat
Price:$113 AUD / night
Downtown Roseburg 1921 Craftsman "Desert" Room
SUPERHOSTPrivate room
Downtown Roseburg 1921 Craftsman "Desert" Room
Price:$48 AUD / night
South Umpqua River Escape
SUPERHOSTEntire guesthouse
South Umpqua River Escape
Price:$75 AUD / night
Umpqua Valley Garden Getaway
SUPERHOSTEntire guest suite
Umpqua Valley Garden Getaway
Price:$83 AUD / night
Quiet, relaxing bedroom & welcoming hosts
SUPERHOSTPrivate room
Quiet, relaxing bedroom & welcoming hosts
Price:$60 AUD / night
Tiny House
SUPERHOSTEntire cabin
Tiny House
Price:$53 AUD / night
C&C's Country Cottage Hobby Farm Mountain Retreat
SUPERHOSTFarm stay
C&C's Country Cottage Hobby Farm Mountain Retreat
Price:$98 AUD / night
Peaceful Paradise
SUPERHOSTEntire house
Peaceful Paradise
Price:$113 AUD / night
Lovely 2 Bedrooms ROSEBURG ,OR
SUPERHOSTEntire house
Lovely 2 Bedrooms ROSEBURG ,OR
Price:$134 AUD / night
Riverfront  Retreat - and parking for your BOAT!
SUPERHOSTEntire guesthouse
Riverfront Retreat - and parking for your BOAT!
Price:$119 AUD / night
Big 3 bed./2ba. Home-Umpqua Valley-Close to I-5
SUPERHOSTEntire house
Big 3 bed./2ba. Home-Umpqua Valley-Close to I-5
Price:$143 AUD / night
Cozy Cottage Home jumpoff for Umpqua, Crater Lake
Private room
Cozy Cottage Home jumpoff for Umpqua, Crater Lake
Price:$68 AUD / night
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