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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 34 Vacation Homes in Winston with updated reviews, rates, and availability.

The Watusi Place - A Modern Umpqua Valley Getaway
Outdoor dining

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (34)
"We had a great stay and home was just what was advertised. There were so many personal touches and the owner was great to deal with. There was a problem with the A/C before we arrived which was quickly relayed to us by owner and they had it fixed just after our arrival. We will definitely be back next time we are in town. "
The price is AED 419
AED 1,200 total
includes taxes & fees
8 Apr - 9 Apr
The Watusi Place - A Modern Umpqua Valley Getaway
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Interior

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

The price is AED 915
AED 1,782 total
includes taxes & fees
7 Apr - 8 Apr
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
A Restful Studio Near a Creek and Forest - Pets
Terrace/patio

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (29)
"We stayed here for our honeymoon. It was so clean, open and inviting!Fully stocked bathroom and kitchen.They even left us some oatmeal, coffee and protein bars!Ashley was so sweet!She always responded to me within 5 minutes if I had any questions or needed anything!We had the best time!It is so beautiful there and the bed was so comfy. The walk in shower was the best!I wish I could give a 10 star review!"
The price is AED 349
AED 607 total
includes taxes & fees
7 Apr - 8 Apr
A Restful Studio Near a Creek and Forest - Pets
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
2 bedrooms, desk, iron/ironing board, free WiFi

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

9.8 out of 10, Exceptional, (72)
"Love this little abode and recommend "
The price is AED 459
AED 788 total
includes taxes & fees
7 Apr - 8 Apr
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.
Fridge, microwave, oven, stovetop

Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.

9.2 out of 10, Wonderful, (7)
"The Monroe River House in Roseburg, OR was the perfect home for us. The master bedroom was spacious, and the bed was super comfortable. Having an additional BR and bathroom was a bonus, too. The house and kitchen were well-stocked and had everything we needed and more - like plastic bags to keep food in, etc. The yard was huge, and we spent a few afternoons hanging out at the little beach on the river at the bottom of the property. The area is beautiful with lots of local wineries nearby. We...
Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
Fridge, microwave, oven, stovetop

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

9.6 out of 10, Exceptional, (55)
"We had a wonderful stay. With the number of bedrooms and bathrooms, it was perfect for our group size. The host was great and very responsive when needed. The game room provided a fun time for every one of all ages. With the folding tables and chairs located on site, it provided the perfect amount of seating for our group for our Thanksgiving meal. Would definitely recommend this place and hope to rent it again in the future."
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Outdoor dining

Xenia House-Roseburg Retreat with a View! Near Wildlife Safari

10.0 out of 10, Exceptional, (13)
"We were here for YGB Camp and this housed our entire group and we had extra space if we’d have brought more people! We also asked for late checkout last minute and she was very accommodating. House was very well stocked and clean. We will be returning."
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Indigo Collective - Modern Home
Private kitchen

Indigo Collective - Modern Home

10.0 out of 10, Exceptional, (15)
"The home was clean, comfortable, and everything worked well!A perfect place to stay for your visit to Roseburg, OR!"
The price is AED 825
AED 1,813 total
includes taxes & fees
13 Apr - 14 Apr
Indigo Collective - Modern Home
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Interior

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.6 out of 10, Exceptional, (12)
"Inviting and comfortable "
The price is AED 327
AED 640 total
includes taxes & fees
7 May - 8 May
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Stylish Escape - Chic & Cozy with relaxing backyard
Property grounds

Stylish Escape - Chic & Cozy with relaxing backyard

The price is AED 825
AED 1,837 total
includes taxes & fees
22 Apr - 23 Apr
Stylish Escape - Chic & Cozy with relaxing backyard
Cozy Roseburg Home w/ Fire Pit + Gas Grill!
Hair dryer, towels

Cozy Roseburg Home w/ Fire Pit + Gas Grill!

9.8 out of 10, Exceptional, (11)
"12 day stay small would be good for couple gŕeat appliances ken who lives next door was easy to get along with had things all ready to go when i arrived "
Cozy Roseburg Home w/ Fire Pit + Gas Grill!
Stylish cottage with river views, central location, & modern amenities
1 bedroom, internet, bed sheets

Stylish cottage with river views, central location, & modern amenities

Stylish cottage with river views, central location, & modern amenities
Tiny House nestled into the Forest on 160 acre Playground.
Property grounds

Tiny House nestled into the Forest on 160 acre Playground.

8.6 out of 10, Excellent, (4)
"Cute tiny house on an absolutely lovely, serene forested hillside. Really close to town, all things considered - about 20 minutes from the hospital where I was working for the month! The one downside that is only an issue with more extended stays like mine - the compost toilet did get a tad smelly as the weeks went by. Not to an unbearable degree but just a small caveat to the five stars! "
The price is AED 470
AED 626 total
includes taxes & fees
10 Apr - 11 Apr
Tiny House nestled into the Forest on 160 acre Playground.
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Fridge, microwave, oven, stovetop

Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

9.8 out of 10, Exceptional, (24)
"This place is a great place to stay. Clean, property manager is great, location is a close drive to anything you need. This was our second time there. Will be back again if we are in the area. "
The price is AED 421
AED 1,044 total
includes taxes & fees
7 Apr - 8 Apr
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Family-Friendly Winston Vacation Rental w/ Deck!
Fridge, microwave, stovetop, dishwasher

Family-Friendly Winston Vacation Rental w/ Deck!

10.0 out of 10, Exceptional, (12)
"Very nice place. They have thought of everything. Thanks "
Family-Friendly Winston Vacation Rental w/ Deck!
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Terrace/patio

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

10.0 out of 10, Exceptional, (21)
"Excellent experience! We were passing through and wanted a cozy experience from multiple hotel stays. Our hosts were outstanding and so friendly, attentive to every little detail to make us feel welcomed and comfortable. An outstanding bed and breakfast experience!"
The price is AED 661
AED 820 total
includes taxes & fees
7 Apr - 8 Apr
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Exterior

Red Tiny Twins, Downtown Eco & Pet Friendly Stay

10.0 out of 10, Exceptional, (10)
"Very comfortable "
The price is AED 327
AED 640 total
includes taxes & fees
26 Apr - 27 Apr
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg
Fridge, microwave, oven, stovetop

Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg

9.8 out of 10, Exceptional, (23)
"Perfect "
Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Property grounds

Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

9.6 out of 10, Exceptional, (29)
"This place is worth your money! The beds and bedding are very comfortable. The shower pressure is great. The amenities excel. Very quiet neighborhood. Communication with host is excellent. I will recommend this place to my friends and family. Would stay here again for sure."
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Property grounds

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (24)
"We have stayed at this property now multiple times and it has been clean, easy, great location, everything works and we will definitely be back"
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
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 property types in Winston

The Watusi Place - A Modern Umpqua Valley Getaway
Outdoor dining

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (34)
"We had a great stay and home was just what was advertised. There were so many personal touches and the owner was great to deal with. There was a problem with the A/C before we arrived which was quickly relayed to us by owner and they had it fixed just after our arrival. We will definitely be back next time we are in town. "
The price is AED 419
AED 1,200 total
includes taxes & fees
8 Apr - 9 Apr
The Watusi Place - A Modern Umpqua Valley Getaway
Family-Friendly Winston Vacation Rental w/ Deck!
Fridge, microwave, stovetop, dishwasher

Family-Friendly Winston Vacation Rental w/ Deck!

10.0 out of 10, Exceptional, (12)
"Very nice place. They have thought of everything. Thanks "
Family-Friendly Winston Vacation Rental w/ Deck!
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
Fridge, microwave, oven, stovetop

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

9.6 out of 10, Exceptional, (55)
"We had a wonderful stay. With the number of bedrooms and bathrooms, it was perfect for our group size. The host was great and very responsive when needed. The game room provided a fun time for every one of all ages. With the folding tables and chairs located on site, it provided the perfect amount of seating for our group for our Thanksgiving meal. Would definitely recommend this place and hope to rent it again in the future."
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
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.