Winston Holiday Rentals

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Winston holiday rentals

Dining

The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (48 reviews)
"The house was amazing! Easy to get in, clean and well stocked. Definitely recommend to anyone looking for a nice place."
United States
Amy H.
The price is HK$1,289
HK$3,009 total
includes taxes & fees
19 Feb - 20 Feb
The Watusi Place - A Modern Umpqua Valley Getaway
Dining

Charming cottage studio in serene environment perfect for a relaxing getaway

Charming cottage studio in serene environment perfect for a relaxing getaway
Winston
The price is HK$1,250
HK$1,427 total
includes taxes & fees
8 Mar - 9 Mar
Charming cottage studio in serene environment perfect for a relaxing getaway
Property grounds

Starry Skies Campout

Starry Skies Campout
Douglas County
The price is HK$492
HK$658 total
includes taxes & fees
8 Feb - 9 Feb
Starry Skies Campout
Property grounds

Madrone Hideout, Madrone Hideout Chariot

Madrone Hideout, Madrone Hideout Chariot
Douglas County
The price is HK$902
HK$1,653 total
includes taxes & fees
25 Feb - 26 Feb
Madrone Hideout, Madrone Hideout Chariot
Terrace/patio

A Restful Studio Near a Creek and Forest - Pets

A Restful Studio Near a Creek and Forest - Pets
Roseburg
10.0 out of 10, Exceptional, (42 reviews)
"Enjoyed our stay!"
United States
Dana M.
The price is HK$742
HK$1,291 total
includes taxes & fees
6 Feb - 7 Feb
A Restful Studio Near a Creek and Forest - Pets
Terrace/patio

Lil Cedar Lodge

Lil Cedar Lodge
Roseburg
The price is HK$668
HK$876 total
includes taxes & fees
8 Feb - 9 Feb
Lil Cedar Lodge
Property grounds

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

Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly
Riddle
9.8 out of 10, Exceptional, (90 reviews)
"My wife and I travel a lot with our little dachshund. This property is one of the nicest private offerings we have ever experienced. The owner has created a perfectly lovely and cozy little apartment for two. It is completely stocked and meticulously well-organized. The owner is also gracious and very flexible. An ideal place to stay."
United States
Dale
The price is HK$703
HK$1,150 total
includes taxes & fees
6 Feb - 7 Feb
Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly
Property grounds

Charming, Private Cottage near I-5 and Golf Course.

Charming, Private Cottage near I-5 and Golf Course.
Myrtle Creek
10.0 out of 10, Exceptional, (42 reviews)
"This is the second time I have stayed here, both times with my dog. The place is convenient, quiet, clean, comfortable, and with great touches and landscaping outside. Wonderful place."
United States
Carter L.
The price is HK$1,246
HK$1,405 total
includes taxes & fees
6 Feb - 7 Feb
Charming, Private Cottage near I-5 and Golf Course.
Smart TV, fireplace, books, music library

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

Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Roseburg
9.8 out of 10, Exceptional, (39 reviews)
"We had a great stay while we visited family. The house had everything we needed, and the new mattresses were very comfortable. Gary was easy to get ahold of and responded quickly. We would stay again. "
United States
Riley E.
The price is HK$737
HK$2,158 total
includes taxes & fees
9 Feb - 10 Feb
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Exterior

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Roseburg
9.6 out of 10, Exceptional, (37 reviews)
"Nice place, great location."
United States
Gordon
The price is HK$977
HK$1,754 total
includes taxes & fees
8 Mar - 9 Mar
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Exterior detail

Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.4 out of 10, Exceptional, (19 reviews)
"Just the right size and location for a wine country getaway weekend. Had everything we needed, and more. Will not hesitate to book again next trip, if it's available."
United States
John L.
The price is HK$742
HK$1,412 total
includes taxes & fees
6 Feb - 7 Feb
Downtown Stay at the Blue Tiny Twin
Living area

Home Sweet Home

Home Sweet Home
Sutherlin
8.6 out of 10, Excellent, (10 reviews)
"This location worked great for our visit with family in the area. The house was clean and the beds were comfortable. Host was easy to work with - thanks!"
United States
Barbara S.
The price is HK$938
HK$2,669 total
includes taxes & fees
7 Feb - 8 Feb
Home Sweet Home
Exterior

Tiny House nestled into the Forest on 160 acre Playground.

Tiny House nestled into the Forest on 160 acre Playground.
Roseburg
9.6 out of 10, Exceptional, (13 reviews)
"Wonderful environment and very peaceful stay. "
United States
Sarah C.
The price is HK$900
HK$1,231 total
includes taxes & fees
6 Feb - 7 Feb
Tiny House nestled into the Forest on 160 acre Playground.
Terrace/patio

Orchard House, Orchard House Retreat

Orchard House, Orchard House Retreat
Douglas County
10.0 out of 10, Exceptional, (1 review)
"Fantastic place to spend the holiday very serene very peaceful"
United States
Gin H.
The price is HK$738
HK$1,455 total
includes taxes & fees
8 Feb - 9 Feb
Orchard House, Orchard House Retreat
Terrace/patio

Blissful Solitude Cottage

Blissful Solitude Cottage
Douglas County
10.0 out of 10, Exceptional, (4 reviews)
"My trip actually got canceled last minute, but the communication with the host was absolutely amazing and I will absolutely rebook as soon as possible"
United States
steve
The price is HK$771
HK$1,410 total
includes taxes & fees
8 Feb - 9 Feb
Blissful Solitude Cottage
Exterior detail

Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (21 reviews)
"It was a perfect place for us to stay for a short trip to visit family with our two little dogs."
United States
Rochelle S.
The price is HK$742
HK$1,412 total
includes taxes & fees
4 Mar - 5 Mar
Downtown Stay at the Red Tiny Twin!
Terrace/patio

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

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Roseburg
10.0 out of 10, Exceptional, (24 reviews)
"Absolutely the most delightful and magical place to stay! Wonderfully gracious hosts! They made our honeymoon stay spectacular and special! James and Gail are fabulous. We had the most incredible breakfast as well. We felt like royalty! "
United States
Rachel S.
The price is HK$1,516
HK$1,857 total
includes taxes & fees
6 Feb - 7 Feb
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Outdoor dining

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Azalea
9.4 out of 10, Exceptional, (22 reviews)
"Wonderful and peaceful place to stay! Breakfast accommodations were above and beyond and such a pleasant surprise! Highly recommend this cute place!"
United States
Connie H.
The price is HK$1,392
HK$2,373 total
includes taxes & fees
9 Feb - 10 Feb
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Exterior

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

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Roseburg
9.8 out of 10, Exceptional, (91 reviews)
"Thank you so much for the comfy cozy place to stay! "
United States
Kristina C.
The price is HK$938
HK$1,625 total
includes taxes & fees
9 Feb - 10 Feb
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Smart TV

Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Roseburg
9.6 out of 10, Exceptional, (53 reviews)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
The price is HK$859
HK$1,412 total
includes taxes & fees
6 Feb - 7 Feb
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
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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Top Winston Hotel Reviews

Motel 6 Roseburg, OR

Motel 6 Roseburg, OR

10/10 Excellent
"Yes it was perfect"
Matthew 2-night trip
Posted 3 days ago
Motel 6 Roseburg, OR

Find out more about Winston

Search for holiday rentals in Winston on Expedia! You can easily find your home rentals, villas, holiday apartments in Winston using one of the methods below:

  • View our selection of featured holiday rentals in Winston
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  • Enter your travel dates to view the best deals on holiday rentals in Winston while they last

Look no further and take a look at our great range of rental properties in Winston!

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?

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen : 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 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and an arcade/games room. 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.