Holiday rentals in Winston

Mid-Century Retreat: Discover Modern Serenity

Discover a cozy retreat designed for those who love style, comfort, and the warmth of home. Welcome to The Berd Haus, a mid-century modern escape in Roseburg’s tranquil West Harvard neighborhood. Whether you’re sipping wine on the patio, unwinding in a plush bed, or savoring morning coffee in a sunlit living room, every detail is crafted for relaxation and connection. Just minutes from wineries, outdoor adventures, and the best of Southern Oregon, this stylish home is your perfect getaway.

Mountain View Treehouse

Perched 17 feet above the forest floor between four mature Douglas fir trees and ready for your relaxing escape. You may catch a glimpse of a blacktail deer, turkey, grey squirrel, or hear a great horned owl or woodpecker. No comfort is left out, equipped with an unlimited hot water shower, toilet, sink, heat and ac. The interior of the treehouse is lined with incense cedar harvested on the property. Small decks off the front and back of the treehouse to relax and enjoy your morning coffee.

Cinder Cottage ~ No Cleaning Fee

Cinder Cottage is a cozy and clean 2 bedroom home that's been recently updated and is pet & family friendly. Located on a quiet corner in the heart of historic Riddle OR just a block from the high school and walking distance to the small downtown. A few miles from the I-5 corridor it's a great place to stop for a break from driving. We're just minutes away from Seven Feathers Casino in Canyonville. Whether you're traveling, exploring or visiting friends or family come relax at Cinder Cottage.

The Cottages at Porter Hill (Green)-Near Roseburg

Welcome to The Cottages at Porter Hill, nestled in the heart of Umpqua Valley Wine Country. A perfect retreat for two! This cozy 1 bedroom cottage is inspired by the green fields of central Italy & simple country living. We invite you to slow down, relax and experience our little slice of heaven! Conveniently located on Highway 42 with easy access to Winston, the Wildlife Safari and Roseburg (10 - 15 minutes) to the east and the Oregon coast-Coos Bay and Bandon (just 1.5 hours) to the west.

The Hippie Shack Yurt +Tiny House + Farm Breakfast

This elegant 24-ft cedar-lined yurt features hardwood floors, heat, A/C, queen bed & queen futon. Open and airy with a clear dome to stargaze from bed! A private attached tiny home includes a bathroom with hot shower and a full kitchen with propane stove, fridge, coffee maker (no microwave). Free continental breakfast: croissants, jelly, yogurt w/ fruit, oatmeal, juice, coffee & tea. Private farm setting near river, animals roam outside. 15 min to Canyonville, 40 min to Safari. Organic farm !

The Loft@Paradise Point. Hot tub w/stunning views!

Relax and unwind at this unique, secluded, sparkling clean, getaway. The Loft is situated behind a private security gate on top of a mountain. It has breathtaking views yet is only 10 min. from town and in the heart of some of the greatest wineries in Oregon. The bedroom has a romantic fireplace and access to a private deck. Equipped with a Refrigerator, K-Cup Coffee Maker, Air-Fryer, Toaster Oven & Microwave. Soak in the new luxurious hot tub that has WIFI. Fire pit offered when permitted.

Aviation Suites: Flight Deck

Aviation Suites is a unique business setting with overnight accommodations on the tarmac of the Roseburg Airport. Quality best describes the experience. The Flight Deck’s floor to ceiling windows lets you experience the thrill of the runway. The Hangar is quiet and easily accessible to the best of what Douglas County has to offer. An adjoining door offers a third option, a two bedroom, two bath executive suite. Private & accessible by air or vehicle. Book your stay now at Aviation Suites!

Twin palms

Spend time with the whole family. Very new and modern amenities. Handicap accessible. 7 bed rooms and 5 bathrooms. Bring the whole family and spend time at wildlife safari. Or go hiking/biking/fishing/hunting on the famous north umpqua river. 45 miles of dedicated fly fishing with some of the best steelhead fishing in the world. Crader lake is a wonderful day trip as you travel up the north umpqua river. If you like wine,try a tour with A Touch Of Class limousines Ring doorbell on site.

Hawthorne Haus

Classic mid century home sitting above downtown Roseburg with 3 bedrooms and 2.5 baths. Home has beautiful views of the city from each of its five decks. Home is fully furnished with everything you'll need to relax, or work with a private office space and high speed WiFi. Walking distance to shopping and dining. Use as your base to explore Southern Oregon with trips to the Oregon Coast, Wildlife Safari, or hiking/fishing/rafting in the Umpqua National Forest. Dogs welcome with a fee.

Riverfront Hideaway - Hot Tub - Private Entrance

Kick back and relax in this calm, stylish retreat tucked along the river in the heart of wine country. With peaceful river views and private river access just steps away, you’ll feel immersed in nature—yet still enjoy the convenience of being only a quick 10-minute drive into town. Fishing, agriculture, local activities, and abundant wildlife surround our tranquil hideaway, and it’s easy to see why we fell in love with this special place. Come unwind and soak in the serenity.

Peaceful Paradise

Very clean and private. Great Base to get out and explore or to relax. We are located on the way to North Umpqua and the North entrance of Crater lake both boast of beautiful waterfalls and amazing hikes! We are located less than 2 miles off the 5 freeway . The area has everything from restaurants, wineries and outdoor activities. A short 15 minutes away is Wildlife Safari which we offer discount tickets. Whether it's overnight or longer you'll love it here!

Umpqua Valley Garden Getaway

Minutes from several award-winning wineries and local fishing holes, the Umpqua Valley Garden Getaway has all the amenities you will need for a memorable vacation. Down a cobblestone stairway, you will find a pristinely redesigned cottage nestled in a private backyard garden. Start your day with a hot cup of coffee from the wicker chairs overlooking the backyard and end your day dining al fresco as string lights dangle above a cozy corner of the deck.