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Holiday Homes in Winston

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Winston

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Enjoy a convenient coffee station with a coffee maker and coffee available, perfect for a morning pick-me-up.

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

9.8 out of 10, Exceptional, (82)
"Love this little abode and recommend "
The price is AU$339
includes taxes & fees
7 Sept - 8 Sept
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Relax on the patio with a wicker table, two chairs, and a small table amidst a grassy lawn and a wooden fence.

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (27)
"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 AU$339
includes taxes & fees
21 Aug - 22 Aug
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Tiny House nestled into the Forest on 160 acre Playground.
Escape to a secluded cabin surrounded by lush greenery, offering a peaceful retreat amidst nature.

Tiny House nestled into the Forest on 160 acre Playground.

9.4 out of 10, Exceptional, (9)
"It was such a nice little spot to get away."
The price is AU$245
includes taxes & fees
21 Aug - 22 Aug
Tiny House nestled into the Forest on 160 acre Playground.
A Restful Studio Near a Creek and Forest - Pets
Enjoy a serene view of the surrounding grassy field and trees from this deck.

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (34)
"Peaceful and clean."
The price is AU$284
includes taxes & fees
6 Sept - 7 Sept
A Restful Studio Near a Creek and Forest - Pets
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and dishwasher.

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

9.8 out of 10, Exceptional, (29)
"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 AU$491
includes taxes & fees
27 Aug - 28 Aug
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Enjoy cooking in this well-equipped kitchen with a gas stove, microwave, and range hood.

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

9.4 out of 10, Exceptional, (9)
"great property"
The price is AU$874
includes taxes & fees
11 Aug - 12 Aug
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
The Watusi Place - A Modern Umpqua Valley Getaway
Enjoy dining or socializing in this patio area with a grill and comfortable seating.

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (39)
"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 AU$544
includes taxes & fees
13 Aug - 14 Aug
The Watusi Place - A Modern Umpqua Valley Getaway
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Relax on the covered patio with comfortable outdoor furniture, surrounded by a lush lawn and a fence.

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

9.6 out of 10, Exceptional, (20)
"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
Enjoy cooking in this well-equipped kitchen with a large island, sink, and modern appliances.

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
Relax on the sofa with a choice of pillows in various patterns.

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.6 out of 10, Exceptional, (18)
"Inviting and comfortable "
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Simple, single-story building with a front porch and entrance.

Red Tiny Twins, Downtown Eco & Pet Friendly Stay

9.8 out of 10, Exceptional, (12)
"Enjoyed the accommodations. just as advertised would stay again."
The price is AU$271
includes taxes & fees
7 Sept - 8 Sept
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Luxury Riverfront Escape- Hot tub & Fire Pit
Enjoy cooking in this well-equipped kitchen with a central island stove, sink, and ample counter space.

Luxury Riverfront Escape- Hot tub & Fire Pit

9.6 out of 10, Exceptional, (11)
"We fit a lot in during our 4 day stay! A trip to Bandon to enjoy the ocean, wine tasting at Cooper Ridge and Knostman Family Winery, and waterfalls. We enjoyed the fire pit and hot tub each night. The house was nicely decorated and met all of our needs! We walked the neighborhood and spent time at the river. Abby was spot on with her communication. We highly recommend booking a stay at the Monroe River House!"
Luxury Riverfront Escape- Hot tub & Fire Pit
Home Sweet Home
Private kitchen

Home Sweet Home

10.0 out of 10, Exceptional, (2)
"Truly enjoyed staying at "Home Sweet Home". Beds are very comfortable, home was very clean, hosts were quick to respond and give info through texts. Would definitely recommend staying here. Looking for a great place to stay while check out the wineries? You found the place."
Home Sweet Home
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
Enjoy cooking in this well-equipped kitchen with a refrigerator, coffee maker, and wooden cabinets.

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

9.6 out of 10, Exceptional, (58)
"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
Fisherman’s paradise in wine country. www.umpquariverlodge.com
Fridge, microwave, oven, stovetop

Fisherman’s paradise in wine country. www.umpquariverlodge.com

Fisherman’s paradise in wine country. www.umpquariverlodge.com
Stylish Escape - Chic & Cozy with relaxing backyard
Relax by the fire pit in an outdoor seating area surrounded by comfortable chairs.

Stylish Escape - Chic & Cozy with relaxing backyard

10.0 out of 10, Exceptional, (3)
"Great place to stay. Was clean and updated older house, with a big back yard. Perfect for my wife, three kids, three granddaughters, and I."
Stylish Escape - Chic & Cozy with relaxing backyard
Blissful Solitude Cottage
Relax in the serene outdoor seating area with comfortable chairs and tables, surrounded by lush greenery and potted plants.

Blissful Solitude Cottage

The price is AU$305
includes taxes & fees
11 Aug - 12 Aug
Blissful Solitude Cottage
Indigo Collective - Modern Comfort & Bold Design
Enjoy cooking in this kitchen with a central island, bar stools, a refrigerator, and oven.

Indigo Collective - Modern Comfort & Bold Design

10.0 out of 10, Exceptional, (21)
"We were only at this house for one quick night stay, but found it very comfortable. "
Indigo Collective - Modern Comfort & Bold Design
Family-Friendly Winston Vacation Rental w/ Deck!
Enjoy cooking in this kitchen with a central island, bar stools, stainless steel appliances, and a large window.

Family-Friendly Winston Vacation Rental w/ Deck!

10.0 out of 10, Exceptional, (18)
"Very nice place. They have thought of everything. Thanks "
Family-Friendly Winston Vacation Rental w/ Deck!
Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, oven, and dishwasher.

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

9.8 out of 10, Exceptional, (27)
"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
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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