Search Holiday Rentals in Winchester

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Top Holiday Rentals in Winchester

River Vista Vacation Homes
Property grounds
River Vista Vacation Homes
3.0 star property
9.0 out of 10, Wonderful, (44)
"I loved the wild river right out the door"
River Vista Vacation Homes
Family-friendly Winston Vacation Rental w/ Deck!
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher
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!
Interior
Cozy Roseburg Home w/ Fire Pit + Gas Grill!
3.0 star property
9.0 out of 10, Wonderful, (2)
"Attractive tiny house, well equipped, peaceful neighborhood, convenient to town. Bedroom is a bit small, but living area and bath (with shower and washer/dryer) are good sized. Helpful owner suggested Brix local restaurant we really liked too. Nearby Upper Umpquah waterfalls, hiking, river rafting made a nice vacation."
Cozy Roseburg Home w/ Fire Pit + Gas Grill!
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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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Other types of properties in Winchester you may be interested in

Riverfront Inn Roseburg
BBQ/picnic Area
Riverfront Inn Roseburg
2.0 star property
8.6 out of 10, Excellent, (1196)
"staff welcoming and hospitable, bed very comfortable, and breakfast was perfect for our needs. older building but well maintained. was very convenient to our Roseburg destination."
The price is ₹9,029
₹9,887 total
includes taxes & fees
1 Oct - 2 Oct
Riverfront Inn Roseburg
Sleep Inn & Suites Roseburg North Near Medical Center
Individually decorated, individually furnished, desk, laptop workspace
Sleep Inn & Suites Roseburg North Near Medical Center
2.5 star property
8.0 out of 10, Very good, (1003)
"Great and fast service. Clean room. Good breakfast."
The price is ₹8,025
₹8,788 total
includes taxes & fees
24 Oct - 25 Oct
Sleep Inn & Suites Roseburg North Near Medical Center
Super 8 by Wyndham Roseburg
In-room safe, desk, iron/ironing board, free cots/infant beds
Super 8 by Wyndham Roseburg
2.5 star property
7.8 out of 10, Good, (1001)
"I had a pleasant stay thanks to the incredibly friendly and helpful staff, who went out of their way to assist with any needs. However, I was disappointed with the breakfast options. There were only bagels and some packaged foods available, which didn’t meet my expectations. I hope they expand their breakfast offerings in the future."
The price is ₹6,538
₹7,159 total
includes taxes & fees
24 Oct - 25 Oct
Super 8 by Wyndham Roseburg
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.

Frequently asked questions

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing 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. Melrose Vineyards and Reustle Prayer Rock Vineyards are a couple of places you'll find in the wider area.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family trip.