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Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

Compare 36 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, (36)
"We stayed here for a night since we had a nearby disc golf tournament. Leah was a great host and the house was super clean and comfy. Quiet neighborhood, cool back porch to hang out. Highly recommend! Thank you Leah!"
The price is SAR 428
SAR 1,221 total
includes taxes & fees
30 Apr - 1 May
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

8.0 out of 10, Very Good, (1)
The price is SAR 934
SAR 1,820 total
includes taxes & fees
27 Apr - 28 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, (31)
"Such an amazing property and the house is absolutely perfect! The attention to detail is on point. If I could live here, I would. A perfect quiet retreat just miutes from Roseburg. Will definitely book again! "
The price is SAR 356
SAR 620 total
includes taxes & fees
27 Apr - 28 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, (73)
"We were in town for a tennis tournament at the Umqua Valley Tennis Center and the house was clean and perfect location"
The price is SAR 469
SAR 809 total
includes taxes & fees
12 May - 13 May
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Luxury Riverfront Escape- Hot tub & Fire Pit
Fridge, microwave, oven, stovetop

Luxury Riverfront Escape- Hot tub & Fire Pit

9.4 out of 10, Exceptional, (9)
"Beautiful, quiet, comfortable, clean. 5 stars"
Luxury Riverfront Escape- Hot tub & Fire Pit
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, (56)
"This was amazing stay. Great location, close to every place we wanted to go. It was very nice and clean. We will definitely be staying again. "
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 Comfort & Bold Design
Private kitchen

Indigo Collective - Modern Comfort & Bold Design

10.0 out of 10, Exceptional, (16)
"We were in Roseburg on business for over a month. We stayed at this home and it was perfect very clean close to town. And the owner was always there if we needed something."
The price is SAR 883
SAR 1,916 total
includes taxes & fees
1 May - 2 May
Indigo Collective - Modern Comfort & Bold Design
Stylish Escape - Chic & Cozy with relaxing backyard
Property grounds

Stylish Escape - Chic & Cozy with relaxing backyard

The price is SAR 883
SAR 1,928 total
includes taxes & fees
1 May - 2 May
Stylish Escape - Chic & Cozy with relaxing backyard
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 SAR 334
SAR 653 total
includes taxes & fees
30 Apr - 1 May
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Cozy Roseburg Home w/ Fire Pit + Gas Grill!
Hair dryer, towels

Cozy Roseburg Home w/ Fire Pit + Gas Grill!

9.6 out of 10, Exceptional, (10)
"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 SAR 480
SAR 640 total
includes taxes & fees
26 Apr - 27 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 SAR 401
SAR 1,051 total
includes taxes & fees
27 Apr - 28 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, (13)
"From individual air conditioning units to a plethora of kids toys this stay was perfectly set up for our family to enjoy the wild animal safari. 10/10 would stay again! "
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 SAR 675
SAR 842 total
includes taxes & fees
28 Apr - 29 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 SAR 334
SAR 653 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

9.6 out of 10, Exceptional, (24)
"We had a great time! The hosts were very fast in responding to any questions we had and the house was clean, comfortable and had all the amenities to make it a great family trip!"
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, (36)
"We stayed here for a night since we had a nearby disc golf tournament. Leah was a great host and the house was super clean and comfy. Quiet neighborhood, cool back porch to hang out. Highly recommend! Thank you Leah!"
The price is SAR 428
SAR 1,221 total
includes taxes & fees
30 Apr - 1 May
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, (13)
"From individual air conditioning units to a plethora of kids toys this stay was perfectly set up for our family to enjoy the wild animal safari. 10/10 would stay again! "
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, (56)
"This was amazing stay. Great location, close to every place we wanted to go. It was very nice and clean. We will definitely be staying again. "
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.