Photo by Michelle Finseth

Winston Holiday Rentals

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Holiday Rentals in Winston

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 AU$513
includes taxes & fees
19 Feb - 20 Feb
The Watusi Place - A Modern Umpqua Valley Getaway

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!

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!

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (47)
"We are repeat renters and thoroughly enjoy our home away from home every year. Thank you!"
Firewater Lodge Cabin Experience

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

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 AU$263
includes taxes & fees
17 Feb - 18 Feb
A Restful Studio Near a Creek and Forest - Pets

Lakefront Cabin in the Forest Breakfast Included

9.8 out of 10, Exceptional, (6)
"Amazing, beautiful, perfect..."
The price is AU$471
includes taxes & fees
17 Feb - 18 Feb
Lakefront Cabin in the Forest Breakfast Included

Xenia House-Roseburg Retreat with a View!

10.0 out of 10, Exceptional, (10)
"We have stayed at this house on previous trips to the Roseburg area. It is always a relaxing stay at this house. The rooms are clean and the house is located near our daughter and her family."
Xenia House-Roseburg Retreat with a View!

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 AU$694
includes taxes & fees
17 Feb - 18 Feb
The Bucket List Retreat

<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 AU$347
includes taxes & fees
19 Feb - 20 Feb
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

Indigo Collective - Modern Home

10.0 out of 10, Exceptional, (14)
"Enjoyed our stay. Had everything we needed"
The price is AU$759
includes taxes & fees
25 Feb - 26 Feb
Indigo Collective - Modern Home

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

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

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!

Just off I-5, RV available on secluded lot. 2 livestock stalls. Close to town.

10.0 out of 10, Exceptional, (3)
"Stayed here while figuring out my living situation during the sale of my place. Doug was so helpful and kind. I love the setting, watching cows graze while drinking coffee in the morning. Bed is comfortable. Very quiet. If you like a little solitude while RV'ing, you should enjoy it here."
Just off I-5, RV available on secluded lot. 2 livestock stalls. Close to town.

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 AU$272
includes taxes & fees
2 Mar - 3 Mar
Tiny House nestled into the Forest on 160 acre Playground.

Lost World Lodge - Your Jurassic Park Vacation Rental

9.4 out of 10, Exceptional, (6)
"Our stay was wonderful. The apartment was big clean and so comfortable. All of the beds every comfortable and lots of pillows and plenty of towels and toiletries. The kitchen was well set up plenty of coffee and tea cookware and dinnerware. Bring your own spices and food. Will Vero come back. "
Lost World Lodge - Your Jurassic Park Vacation Rental

Lil Cedar Lodge

The price is AU$195
includes taxes & fees
17 Feb - 18 Feb
Lil Cedar Lodge

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.

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 AU$288
includes taxes & fees
17 Feb - 18 Feb
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
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 Winston you may be interested in

Safari Inn

2.0 star property
7.6 out of 10, Good, (340)
"Everything is fine, hotel like usual."
The price is AU$101
includes taxes & fees
17 Feb - 18 Feb
Safari Inn

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

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 AU$513
includes taxes & fees
19 Feb - 20 Feb
The Watusi Place - A Modern Umpqua Valley Getaway
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

Are there holiday rentals in Winston?

Yes, there are holiday rentals in Winston close to Wildlife Safari, or you can select a more secluded option if you're looking for a relaxing stay. Winston is known for its restaurants.

What are some of the best holiday rentals that Winston has to offer?

Family-Friendly Winston Vacation Rental w/ Deck!: This highly rated holiday home rental in Winston offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind. Another good choice for your trip to Winston is The Watusi Place - A Modern Umpqua Valley Getaway.

How many holiday rentals will I find in Winston?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Winston stay.

What’s there to see and do in Winston?

Family-friendly attractions include Wildlife Safari, whereas South Umpqua River is a spot to enjoy the outdoors. In the wider area, you’ll find Abacela Winery and Melrose Vineyards.

What’s a holiday rental in Winston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winston. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a small group gathering.