Photo by Michelle Finseth

Winston Holiday Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
7 Jul - 8 Jul
Tomorrow
8 Jul - 9 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals 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, (38)
"Enjoyed the house and area! Great stay on the way to Crater Lake from the coast!"
The price is HK$1,095
HK$2,823 total
includes taxes & fees
15 Jul - 16 Jul
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, (17)
"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, (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
Family-friendly Winston Vacation Rental w/ Deck!
Interior

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!
Lakefront Cabin in the Forest ✨️ A Vacation Wonderland ✨️
Outdoor dining

Lakefront Cabin in the Forest ✨️ A Vacation Wonderland ✨️

9.4 out of 10, Exceptional, (13)
"Perfect"
The price is HK$1,328
HK$2,328 total
includes taxes & fees
8 Jul - 9 Jul
Lakefront Cabin in the Forest ✨️ A Vacation Wonderland ✨️
<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, (79)
"Love this little abode and recommend "
The price is HK$981
HK$1,719 total
includes taxes & fees
15 Jul - 16 Jul
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly
Interior

Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly

10.0 out of 10, Exceptional, (70)
"As advertised. Perfect for a quick overnight or extended stay. Would not hesitate to stay again. "
The price is HK$589
HK$996 total
includes taxes & fees
23 Jul - 24 Jul
Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly
Tiny House nestled into the Forest on 160 acre Playground.
Property grounds

Tiny House nestled into the Forest on 160 acre Playground.

9.0 out of 10, Wonderful, (6)
"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 HK$904
HK$1,237 total
includes taxes & fees
8 Jul - 9 Jul
Tiny House nestled into the Forest on 160 acre Playground.
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, (33)
"Peaceful and clean."
The price is HK$863
HK$1,439 total
includes taxes & fees
16 Jul - 17 Jul
A Restful Studio Near a Creek and Forest - Pets
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, (25)
"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 price is HK$903
HK$1,719 total
includes taxes & fees
15 Jul - 16 Jul
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
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, (28)
"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. "
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Interior

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

9.8 out of 10, Exceptional, (6)
The price is HK$2,296
HK$4,227 total
includes taxes & fees
8 Jul - 9 Jul
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Firewater Lodge Cabin Experience
Outdoor dining

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (58)
"Such a homey and beautiful house and property. Perfect weather. My whole family is already asking to go back!"
Firewater Lodge Cabin Experience
Lil Cedar Lodge
1 bedroom, bed sheets

Lil Cedar Lodge

The price is HK$671
HK$880 total
includes taxes & fees
11 Jul - 12 Jul
Lil Cedar Lodge
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Outdoor dining

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

9.6 out of 10, Exceptional, (18)
"Very clean and we loved how well stocked it was! Thankful for the garage to park in! Easy to find and easy to check in!"
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Family home
Fridge, microwave, oven, stovetop

Family home

9.6 out of 10, Exceptional, (4)
"I would suggest to everyone to stay here!"
Family home
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Interior

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.4 out of 10, Exceptional, (15)
"Inviting and comfortable "
The price is HK$699
HK$1,367 total
includes taxes & fees
16 Jul - 17 Jul
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
70s Retro Lounge
Miscellaneous

70s Retro Lounge

10.0 out of 10, Exceptional, (4)
"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. "
70s Retro Lounge
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Exterior

Red Tiny Twins, Downtown Eco & Pet Friendly Stay

9.8 out of 10, Exceptional, (12)
"Enjoyed the accommodations. just as advertised would stay again."
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Just off I-5, RV available on secluded lot. 2 livestock stalls. Close to town.
Property grounds

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

9.8 out of 10, Exceptional, (6)
"Great place to stay, especially if you have horses. Owner was quick to respond if I had any questions or problems. I would recommend this place for couples, friends, or small families."
Just off I-5, RV available on secluded lot. 2 livestock stalls. Close to town.
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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?

The Watusi Place - A Modern Umpqua Valley Getaway: This highly rated holiday home rental in Winston is located in a rural location, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Another good choice for your trip to Winston is Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen .

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 Stewart Park.

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.