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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

Compare 28 Vacation Homes in Winston with updated reviews, rates, and availability.

Family-Friendly Winston Vacation Rental w/ Deck!
Winston Vacation Rental | 4BR | 2BA | Stairs Required | 1,704 Sq Ft

Family-Friendly Winston Vacation Rental w/ Deck!

9.8 out of 10, Exceptional, (10)
"Rooms are spacious and each have their own controller for heat or air conditioning so you can keep the room temp to your liking. The deck is huge and perfect for hanging outside even in wet weather because it’s totally covered. Nice fully stocked kitchen with a variety of appliances and kitchen utensils. The nice surprise was the garage with the ping pong table and work out equipment. They also provide a stroller high chair and pak n play if you have a baby"
Family-Friendly Winston Vacation Rental w/ Deck!
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Spacious living room with a large 65” Smart TV, perfect for a fun movie night.

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

9.8 out of 10, Exceptional, (23)
"Gary was amazing, the house was super clean and well stocked. I was on a work trip so i was only there in the evenings, but it was perfect! Id love to ce back!"
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
A Restful Studio Near a Creek and Forest - Pets
Everything you need in one room!

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (24)
"Perfect! We needed a place to stay on our way up to Washington. We have a dog over 100 lbs and it’s very hard to find a hotel that will take him. This place was very clean, beautiful renovations and very dog friendly. Wish we could have stayed longer, will definitely stay again! "
The price is SAR 356
SAR 620 total
includes taxes & fees
18 Feb - 19 Feb
A Restful Studio Near a Creek and Forest - Pets
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Living area

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

9.8 out of 10, Exceptional, (71)
"Love this little abode and recommend "
The price is SAR 469
SAR 817 total
includes taxes & fees
19 Feb - 20 Feb
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
The Bucket List Retreat
Exterior

The Bucket List Retreat

9.6 out of 10, Exceptional, (25)
"The home was comfortable for all. Kitchen was very functional for preparing food for 8. Wished for better weather so we could have enjoyed the fire pit in the beautiful backyard."
The price is SAR 658
SAR 1,637 total
includes taxes & fees
18 Feb - 19 Feb
The Bucket List Retreat
Indigo Collective - Modern Home
Living area

Indigo Collective - Modern Home

10.0 out of 10, Exceptional, (14)
"Enjoyed our stay. Had everything we needed"
The price is SAR 799
SAR 1,790 total
includes taxes & fees
25 Feb - 26 Feb
Indigo Collective - Modern Home
The Watusi Place - A Modern Umpqua Valley Getaway
Living area

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 SAR 416
SAR 1,209 total
includes taxes & fees
19 Feb - 20 Feb
The Watusi Place - A Modern Umpqua Valley Getaway
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Living area

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
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Exterior detail

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.6 out of 10, Exceptional, (12)
"Inviting and comfortable "
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Cozy Roseburg Home w/ Fire Pit + Gas Grill!
Roseburg Vacation Rental | 1BR | 1BA | 880 Sq Ft | 2 Steps Required for Access

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!
Tiny House nestled into the Forest on 160 acre Playground.
Exterior

Tiny House nestled into the Forest on 160 acre Playground.

8.8 out of 10, Excellent, (3)
"We had an amazing time here it was so quite and peaceful and the host were amazing we will be going back"
The price is SAR 480
SAR 640 total
includes taxes & fees
2 Mar - 3 Mar
Tiny House nestled into the Forest on 160 acre Playground.
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
A comfortable living space to kick your feet up and watch your favorite show!

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."
The price is SAR 356
SAR 678 total
includes taxes & fees
18 Feb - 19 Feb
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.
Property grounds

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

10.0 out of 10, Exceptional, (6)
"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.
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Terraluna with our new greenhouse!

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
18 Feb - 19 Feb
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg
Exterior detail

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

9.8 out of 10, Exceptional, (22)
"10/10 "
Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg
70s Retro Lounge
Private kitchen

70s Retro Lounge

10.0 out of 10, Exceptional, (2)
"Renee was an absolute delight to communicate with and I’m appreciative of her hospitality. This place is absolutely adorable and secluded. It was a nice and peaceful New Year’s Eve. "
The price is SAR 431
SAR 647 total
includes taxes & fees
18 Mar - 19 Mar
70s Retro Lounge
The Mable LUXE - Calming Retreat - Entire Home
Terrace/patio

The Mable LUXE - Calming Retreat - Entire Home

10.0 out of 10, Exceptional, (6)
"Had a great stay and took advantage of the winery that’s in walking distance."
The Mable LUXE - Calming Retreat - Entire Home
Relaxing Riverfront 1875 Farquar Historic Home
Room

Relaxing Riverfront 1875 Farquar Historic Home

2.0 out of 10, (1)
"Unkept property. Unsafe neighborhood. Host never showed up."
Relaxing Riverfront 1875 Farquar Historic Home
Singing Waters at N. Umpqua
View of river from back deck

Singing Waters at N. Umpqua

10.0 out of 10, Exceptional, (5)
"Beautifully decorated house! Loved the view of the river in the backyard. So clean and new! No complaints!!"
Singing Waters at N. Umpqua
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Exterior detail

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
20 Mar - 21 Mar
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
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

Family-Friendly Winston Vacation Rental w/ Deck!
Winston Vacation Rental | 4BR | 2BA | Stairs Required | 1,704 Sq Ft

Family-Friendly Winston Vacation Rental w/ Deck!

9.8 out of 10, Exceptional, (10)
"Rooms are spacious and each have their own controller for heat or air conditioning so you can keep the room temp to your liking. The deck is huge and perfect for hanging outside even in wet weather because it’s totally covered. Nice fully stocked kitchen with a variety of appliances and kitchen utensils. The nice surprise was the garage with the ping pong table and work out equipment. They also provide a stroller high chair and pak n play if you have a baby"
Family-Friendly Winston Vacation Rental w/ Deck!
The Watusi Place - A Modern Umpqua Valley Getaway
Living area

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 SAR 416
SAR 1,209 total
includes taxes & fees
19 Feb - 20 Feb
The Watusi Place - A Modern Umpqua Valley Getaway
Family-friendly Winston Vacation Rental w/ Deck!
Terrace/patio

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!
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.