Winchester Vacation Home Rentals from CA $186: Search Top Private Vacation Homes for Rent

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Our top choices for Winchester vacation homes

A small, single-story house with a green door, white trim, and a small porch.

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

Roseburg

Norma B.

CA $322 total

includes taxes & fees

Oct 31 - Nov 1

A modern house with a stone pathway leading to the entrance, surrounded by various plants and a large planter.

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

Roseburg

Nicole B.

CA $278 total

includes taxes & fees

Nov 1 - Nov 2

A house with a covered porch, a seating area with a sofa and armchair, and a small table.

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

Roseburg

Cindan G.

CA $296 total

includes taxes & fees

Nov 1 - Nov 2

A wooden cabin with a deck, outdoor seating, and a pathway lit by ground lights.

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

Roseburg

kimberley

CA $186 total

includes taxes & fees

Nov 4 - Nov 5

A small house with a porch and string lights.

5. Downtown Stay at the Red Tiny Twin!

Roseburg

Sue S.

CA $232 total

includes taxes & fees

Nov 1 - Nov 2

A wooden deck with a white railing, a potted plant, and a table.

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

Roseburg

"Our hosts, James and Gail, are so lovely. They really care about their guests experience and I felt they truly cared about our experience. It’s a gorgeous home that they have decorated meticulously, and made so comfortable for guests to enjoy. The bed was super comfy and the room cozy. The bedding and towels were soft and top notch. They didn’t skimp on anything. Gail is a great cook and provided homemade food, snacks, and drinks. Some items came from her garden. James is a master with sound and...

Susan

CA $345 total

includes taxes & fees

Nov 1 - Nov 2

A living room with a sofa, a coffee table, a fireplace, a TV, and a painting on the wall.

7. Home Sweet Home

Sutherlin

Barbara S.

CA $491 total

includes taxes & fees

Oct 31 - Nov 1

A serene outdoor seating area with string lights, overlooking a body of water and a mountainous backdrop.

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

Roseburg

Laura O.

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Top Winchester Hotel Reviews

SureStay by Best Western Roseburg

8/10 Good

"I realize the hotel is under construction and the parking lot is somewhat occupied with big trash bins. It was not like that last year when we came, so I am expecting that this is temporary. We really like the new renovations and the pool area is always wonderful! The room with the sofa bed that sleeps 6 was very spacious and comfortable. It is nice that they provide a breakfast at all, but I am allergic to eggs and needed sliced ham or sausages for protein and not just eggs. We were there for a business trip and had several pieces of clothing to hang, but there is no closet OR even a chest of drawers to fold and store your clothing. We had clothes draped all over the sofa, the beds and the desk. The employees were super helpful and nice and tried to help us with everything we needed. There needs to be a water bottle fill up somewhere instead of just a drinking fountain. I cannot fill up my large water bottle in the drinking fountain AND there is no tub in the room to do it either. I realize Roseburg water is clean, but there is no place to fill up a water bottle, not even in the exercise room. Other than that, this hotel is a good price compared to the other hotels in the area and we will probably stay here again."