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Our top choices for Winchester vacation rentals
1. Bell Sister Flats
Bell Sister Flats2.0 star property
Roseburg
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)
"Beautiful flat! We loved our time there"
"Beautiful flat! We loved our time there"
Daniel
The price is AED 1,158
AED 1,158
AED 1,550 total
includes taxes & fees
5 Nov - 6 Nov
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.
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 IHGRoseburg
10/10 Excellent
We had a great stay. The room was clean and the staff were very friendly and welcoming.
We had a great stay. The room was clean and the staff were very friendly and welcoming.
Anne
Riverfront Inn Roseburg
Riverfront Inn RoseburgRoseburg
10/10 Excellent
Nice room, good view, very comfortable! Super friendly front desk staff when I checked in, nothing to complain about at this hotel.
Nice room, good view, very comfortable! Super friendly front desk staff when I checked in, nothing to complain about at this hotel.
Edward
The Lodge at Roseburg
The Lodge at RoseburgRoseburg
10/10 Excellent
A very comfortable stay and perfect for what we needed. Even though there were multiple families staying there, our room was relatively quiet and we enjoyed ourselves. The river view was lovely. You can't even hear the highway even though it is not that far away.
A very comfortable stay and perfect for what we needed. Even though there were multiple families staying there, our room was relatively quiet and we enjoyed ourselves. The river view was lovely. You can't even hear the highway even though it is not that far away.
Matthew
Hampton Inn & Suites Roseburg
Hampton Inn & Suites RoseburgRoseburg
10/10 Excellent
Though the area has a questionable reputation, this hotel is in a newer area, very quiet and very safe
Though the area has a questionable reputation, this hotel is in a newer area, very quiet and very safe
Bill
Best Western Garden Villa Inn
Best Western Garden Villa InnRoseburg
10/10 Excellent
I really liked the staff was always available if needed, the housekeeping is top of the line. I cannot comment on my dislikes since I had none.
I really liked the staff was always available if needed, the housekeeping is top of the line. I cannot comment on my dislikes since I had none.
Jeffrey
SureStay by Best Western Roseburg
SureStay by Best Western RoseburgRoseburg
10/10 Excellent
clean, easy access to town and interstate. restaurant next door, Albertson's a block away. personable and helpful staff. good mattresses!
clean, easy access to town and interstate. restaurant next door, Albertson's a block away. personable and helpful staff. good mattresses!
carol
Super 8 by Wyndham Roseburg
Super 8 by Wyndham RoseburgRoseburg
10/10 Excellent
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Carrie
Historical John Rast House
Historical John Rast HouseRoseburg
10/10 Excellent
Cheri and Mike are wonderful hosts. We enjoyed our stay. The private tour with the history of the house was a huge plus. Cheri and Mike are proud of the historical significance of the house. The renovations Cheri and Mike did, preserved the heritage. The location is wonderful, walking distance from "downtown" Roseburg. We want to come back. Our room was perfect! Clean and had an in room sink. I loved the sound machines in each room, it helped me sleep better. I wish we could have had another...
Cheri and Mike are wonderful hosts. We enjoyed our stay. The private tour with the history of the house was a huge plus. Cheri and Mike are proud of the historical significance of the house. The renovations Cheri and Mike did, preserved the heritage. The location is wonderful, walking distance from "downtown" Roseburg. We want to come back. Our room was perfect! Clean and had an in room sink. I loved the sound machines in each room, it helped me sleep better. I wish we could have had another...
Cat
Best Western Plus Hartford Lodge
Best Western Plus Hartford LodgeSutherlin
10/10 Excellent
Check in was fast and easy. Our breakfast was delicious. They have a cook on site and he made our breakfast. YUMMY!! You gotta stay just to try his cooking!!! We will be back
Check in was fast and easy. Our breakfast was delicious. They have a cook on site and he made our breakfast. YUMMY!! You gotta stay just to try his cooking!!! We will be back
Theresa
Motel 6 Roseburg, OR
Motel 6 Roseburg, ORRoseburg
10/10 Excellent
This is one of the cleanest and safest Motel 6 properties I have ever stayed. However, it is one of the noisiest, too. Every room is inside the building and I am traveling with my 2 little dogs. They put me in a ground floor room (much appreciated) near the side door which has access to a grassy area. They must put all of us with pets in this area. But all of the activity in the hallways, slamming of doors, a baby crying all hours of the night, I hardly got any sleep at all. But, a bonus is...
This is one of the cleanest and safest Motel 6 properties I have ever stayed. However, it is one of the noisiest, too. Every room is inside the building and I am traveling with my 2 little dogs. They put me in a ground floor room (much appreciated) near the side door which has access to a grassy area. They must put all of us with pets in this area. But all of the activity in the hallways, slamming of doors, a baby crying all hours of the night, I hardly got any sleep at all. But, a bonus is...
Dee
Quality Inn Central Roseburg
Quality Inn Central RoseburgRoseburg
10/10 Excellent
Traveling between Fresno & Seattle. Great stop about 1/2 way. Liked it so we made reservations to stop on the way back next week.
Traveling between Fresno & Seattle. Great stop about 1/2 way. Liked it so we made reservations to stop on the way back next week.
Win
Motel 6 Sutherlin, OR
Motel 6 Sutherlin, ORSutherlin
10/10 Excellent
Nice simple motel.
Nice simple motel.
Jerry
Howard Johnson by Wyndham Roseburg
Howard Johnson by Wyndham RoseburgRoseburg
10/10 Excellent
Staff was more than accommodating.
Staff was more than accommodating.
Susan
Safari Inn
Safari InnWinston
10/10 Excellent
Very clean and well maintained. The staff were very nice and was a quick check in. Very close to the safari as well.
Very clean and well maintained. The staff were very nice and was a quick check in. Very close to the safari as well.
Chrstine
Rice Hill Inn
Rice Hill InnOakland
10/10 Excellent
The price is reasonable and it is very clean. The staff is nice and professional. They are also very good about accommodating their guests to the best of their abilities.
The price is reasonable and it is very clean. The staff is nice and professional. They are also very good about accommodating their guests to the best of their abilities.
Willie-Lee
Shamrock Motel
Shamrock MotelRoseburg
10/10 Excellent
This is a very affordable lodging just outside Roseburg but basically within, right next to everything that could matter for visiting. It is an older motel with almost bare bones amenities, but I found that a refreshing change from every chain lodging looking the same and copying every other chain on upgrades and interior appearance. You will have to wait a while for water to get warm/ hot in the shower, but otherwise the rooms are very clean and spotless and staff is very friendly and...
This is a very affordable lodging just outside Roseburg but basically within, right next to everything that could matter for visiting. It is an older motel with almost bare bones amenities, but I found that a refreshing change from every chain lodging looking the same and copying every other chain on upgrades and interior appearance. You will have to wait a while for water to get warm/ hot in the shower, but otherwise the rooms are very clean and spotless and staff is very friendly and...
Aaron
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 are some of the best vacation rentals that Winchester has to offer?
Private Umpqua River Retreat w/ 2 King Suites & Patio: This vacation home near Winchester is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.
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.