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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winchester vacation rentals

A wooden deck with a view of a lake, a covered patio area, and a dining table.

1. Southern Oregon Cabin: Fire Pit & Private Pond!

Southern Oregon Cabin: Fire Pit & Private Pond!
3.0 star property
Oakland
10.0 out of 10, Exceptional, (1 review)
"Cute little place! Especially liked the patio and outside areas. Inside needs a few finishing touches like coat hooks on back of doors, but place is very new, clean and worked great for our few days there."
United States
Wayne
The price is P7,881
P21,395 total
includes taxes & fees
Sep 27 - Sep 28
Southern Oregon Cabin: Fire Pit & Private Pond!
A modern kitchen with stainless steel appliances, a wooden dining table, and a tufted ottoman.

2. Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
10.0 out of 10, Exceptional, (1 review)
"Beautiful flat! We loved our time there"
United States
Daniel
The price is P17,752
P24,233 total
includes taxes & fees
Sep 14 - Sep 15
Bell Sister Flats
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

Super 8 by Wyndham Roseburg

Super 8 by Wyndham Roseburg

10/10 Excellent
"Very clean and cozy room, perfect for a comfortable overnight stay while heading back home north. I booked at the last minute and ran into a couple of issues on my end, but the front desk was incredibly helpful and made everything easy. I’d definitely stay here again!"
Kendra 1-night trip
Posted 3 hours ago
Super 8 by Wyndham Roseburg

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
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  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find a vacation rental in Winchester?

Yes, we offer vacation rentals near well known sights in Winchester, or you can choose a more secluded option if you want a relaxing place to stay. Winchester is known for its restaurants.

What’s there to see and do in Winchester?

While exploring the area, visit family-friendly sights like Wildlife Safari, or get outside and enjoy nature at North Umpqua River. Winchester Dam and Stewart Park are a couple of places you'll find in the larger area.

What’s a vacation rental in Winchester like?

Vacation rentals are privately owned properties you can book for several days or longer in Winchester. Vacation rentals feature extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family getaway.