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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Winchester vacation homes

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

1. 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 CA $284
CA $356 total
includes taxes & fees
Nov 1 - Nov 2
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
A small, single-story house with a green door, white trim, and a small porch.

2. 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, (45 reviews)
"Nice place, great location."
United States
Gordon
The price is CA $178
CA $329 total
includes taxes & fees
Oct 14 - Oct 15
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
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

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Roseburg
9.8 out of 10, Exceptional, (118 reviews)
"Great stay, very clean. Would stay here again."
United States
Cindan G.
The price is CA $171
CA $303 total
includes taxes & fees
Oct 12 - Oct 13
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
A modern house with a stone pathway leading to the entrance, surrounded by various plants and a large planter.

4. 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, (33 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 CA $157
CA $286 total
includes taxes & fees
Oct 12 - Oct 13
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
A small house with a porch and string lights.

5. Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (29 reviews)
"Close to downtown, well appointed, clean and comfortable. Thanks for a lovely stay!"
United States
Sue S.
The price is CA $115
CA $236 total
includes taxes & fees
Oct 18 - Oct 19
Downtown Stay at the Red Tiny Twin!
A wooden cabin with a deck, outdoor seating, and a pathway lit by ground lights.

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

Tiny House nestled into the Forest on 160 acre Playground.
Roseburg
9.6 out of 10, Exceptional, (19 reviews)
"Great location, nice and quiet easy to get to fantastic hosts."
United States
Lee and Kristy D.
The price is CA $151
CA $197 total
includes taxes & fees
Nov 4 - Nov 5
Tiny House nestled into the Forest on 160 acre Playground.
A living room with a sofa, a coffee table, a fireplace, a TV, and a painting on the wall.

7. Home Sweet Home

Home Sweet Home
Sutherlin
9.0 out of 10, Wonderful, (12 reviews)
"This location worked great for our visit with family in the area. The house was clean and the beds were comfortable. Host was easy to work with - thanks!"
United States
Barbara S.
The price is CA $171
CA $498 total
includes taxes & fees
Oct 19 - Oct 20
Home Sweet Home
A spacious living area with a wooden dining table, black chairs, a ceiling fan, and a television displaying a beach scene.

8. The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (59 reviews)
"Great place for us and the kids after a long day at the wildlife safari!"
United States
Jessica M.
The price is CA $231
CA $552 total
includes taxes & fees
Oct 12 - Oct 13
The Watusi Place - A Modern Umpqua Valley Getaway
A modern house with a gravel driveway, large windows, and a view of a forest.

9. Lone Rock Guest House, 20 acres minutes from the North Umpqua River

Lone Rock Guest House, 20 acres minutes from the North Umpqua River
Glide
10.0 out of 10, Exceptional, (2 reviews)
"I have stayed at probably 100 rental houses in my life - this is hands down my favorite and was best suited for my outdoor boys. There are endless things to do on the property and you are in the center of an outdoor adventure town with lakes, rivers, hikes, waterfalls, fishing and more. It was private, clean, well stocked, comfortable and high quality - and the host was responsive, welcoming and helpful. Thank you for the memories. I hope we can come back for an even longer stay next time."
United States
Secret L.
The price is CA $461
CA $865 total
includes taxes & fees
Oct 18 - Oct 19
Lone Rock Guest House, 20 acres minutes from the North Umpqua River
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.
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Top Winchester Hotel Reviews

Holiday Inn Express & Suites Roseburg North by IHG

Holiday Inn Express & Suites Roseburg North by IHG

10/10 Excellent
"Nice"
Denys 1-night trip
Posted less than an hour ago
Holiday Inn Express & Suites Roseburg North by IHG

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
330
Accommodation
36 Vacation Homes
Lowest Price
CA $197
Highest Price
CA $865

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