Winchester Vacation Rentals

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Vacation Rentals in Winchester

Family-friendly Winston Vacation Rental w/ Deck!
Private kitchen

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!
Shower

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!
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
Bell Sister Flats
Private kitchen

Bell Sister Flats

2.0 star property
The price is P21,996
P28,607 total
includes taxes & fees
Nov 23 - Nov 24
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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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, (1229)
"Stayed here many times, great cozy hotel on the river. "
The price is P5,781
P6,330 total
includes taxes & fees
Dec 1 - Dec 2
Riverfront Inn Roseburg
Best Western Garden Villa Inn
Exterior

Best Western Garden Villa Inn

2.5 star property
8.0 out of 10, Very Good, (1035)
"Great front desk staff on every shift. Very helpful and friendly. "
The price is P5,014
P5,490 total
includes taxes & fees
Dec 3 - Dec 4
Best Western Garden Villa Inn
Super 8 by Wyndham Roseburg
In-room safe, desk, iron/ironing board, free cribs/infant beds

Super 8 by Wyndham Roseburg

2.5 star property
7.6 out of 10, Good, (1000)
"The accessible shower did not have a shower curtain available so water travelled around bathroom floor even whjle being very cautious. Need hooks on door for clothing while showering. The beds were excellent and room quiet, staff very helpful."
The price is P4,153
P4,548 total
includes taxes & fees
Dec 15 - Dec 16
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 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. 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.