Winchester Vacation Rentals

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Oct 11 - Oct 12
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Oct 12 - Oct 13
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Oct 17 - Oct 19
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Oct 24 - Oct 26

Vacation Rentals in Winchester

Bell Sister Flats
Deluxe Apartment, City View | Private kitchen

Bell Sister Flats

2.0 star property
The price is ₩552,565
₩714,399 total
includes taxes & fees
Oct 12 - Oct 13
Bell Sister Flats
River Vista Vacation Homes
Property entrance

River Vista Vacation Homes

3.0 star property
9.2 out of 10, Wonderful, (45)
"The place was right on the river which was beautiful and it had everything that we would need. It was clean and pretty roomy for my family and I to spend the weekend there and we absolutely loved it! We’re already trying to make another trip out here!"
River Vista Vacation Homes
Southern Oregon Cabin: Fire Pit & Private Pond!
House (1 Bedroom) | Interior

Southern Oregon Cabin: Fire Pit & Private Pond!

3.0 star property
10.0 out of 10, Exceptional, (1)
"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."
Southern Oregon Cabin: Fire Pit & Private Pond!
Romantic Vineyard Getaway in Oakland: Mtn Views!
House (1 Bedroom) | Interior

Romantic Vineyard Getaway in Oakland: Mtn Views!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Property was well organized with all the necessities/amenities that made our stay that much more comfortable. Perhaps instructions on how to operate front door lock would be helpful. Otherwise, everything else was perfect. Thank you! "
Romantic Vineyard Getaway in Oakland: Mtn Views!
Family-friendly Winston Vacation Rental w/ Deck!
House (4 Bedrooms) | Front of property

Family-friendly Winston Vacation Rental w/ Deck!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This house was beautiful, affordable, and very spacious! It had every single amenity you would need and many extras too! The host was extremely attentive and informative with check on and out process and also making sure we could contact her at any time if needed. I definitely recommend this house and will stay here again when in the area."
Family-friendly Winston Vacation Rental w/ Deck!
Cozy Roseburg Home w/ Fire Pit + Gas Grill!
House (1 Bedroom) | Interior

Cozy Roseburg Home w/ Fire Pit + Gas Grill!

3.0 star property
9.0 out of 10, Wonderful, (2)
"Host was very responsive. The space is decorated very well with everything you would need. My husband and I will definitely stay again. "
Cozy Roseburg Home w/ Fire Pit + Gas Grill!
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

Howard Johnson by Wyndham Roseburg

Howard Johnson by Wyndham Roseburg

10/10 Excellent
"very nice room "
rick 2-night trip
Posted 2 days ago
Howard Johnson by Wyndham Roseburg

Find out more about Winchester

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

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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 Douglas County Museum of History and Natural History, or get outside and enjoy nature at North Umpqua River. Stewart Park and Melrose Vineyards 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.