Holiday houses in Winston

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.

Bailey River House

Spacious 3 BR 2 bath. The primary bedroom has a king bed. The other 2 rooms have queen beds. The extra bonus room has 2 cots, full sofa sleeper and a Queen platform bed. The home is fully stocked with EVERYTHING you need. NO PETS and NO SMOKING inside the home, especially Marijuana. There will be a $100 -$200 fee if this rule is broken. PARTIES & EVENTS are not allowed until further notice. Airbnb has a global ban of no more than 16 people allowed on the property. Outside cameras in use.

Ranch House #2 +Farm Breakfast Included

Spread out in 1500 sq. ft. of rustic charm! Located in the original barn on our property, this converted duplex features a fully stocked kitchen, full bathroom, and two private bedrooms. One bedroom offers a queen bed and cozy reading chair; the other includes a queen bed and twin bunk beds. The Kids’ Loft & Game Room has two twin beds and a spacious common area with soaring 20’ ceilings—perfect for relaxing after a long day of exploring. Dog-friendly but do not allow cats due to allergies

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.

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.

Rustic Riverfront Cabin

Rustic riverfront cabin only steps from the world famous Umpqua River. 3bd/2ba home on almost an acre nestled in the trees. 2 Pets are permitted with approval and a fee applies, see below. There is a fully furnished kitchen, microwave, coffee maker, stove, dishwasher, pellet stove, barbeque, WIFI, streaming and a good selection of dvd's, books and games available. There is also a full size washer and dryer. The cabin sleeps 6 comfortably (the limit includes infants)

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.

A Restful Studio Near a Creek and Forest - Pets

Please read below for details about the occupancy. We are nestled in the country between Roseburg and Glide. This updated studio is private, clean, restored, and sits atop a 50's cabin. This is a shared guest property, and the parking and entrances are completely separate! Open the windows, listen to the creek, or sit on the porch and look at the trees. We are on the way to the North Umpqua river, many hiking trails, waterfalls, and Crater Lake!

The Circle C Guest House

Dan and Sally, hosts for 9 years, invite you to stay at the Circle C Guest House, a 288sf pet-friendly tiny home on the 9-acre Circle C Ranch 6 miles off I-5 Exit 103 (Riddle/Tri City), which is 22 miles south of Roseburg. Visit Umpqua valley wineries, Wildlife Safari, Cougar Canyon Golf Course and Seven Feathers Casino. Fishing, hunting, swimming, hiking and cycling opportunities nearby. Discounts for stays of 4 or more nights.

Chardonnay Chalet at the Vineyard

Enjoy the ultimate Pacific Northwest getaway in our luxury vineyard guest house. We are perfectly located as a launching point to experience Ocean Beaches (1.5 hours), Crater Lake National Park (2.5 hours), Waterfall Hikes (45 minutes), and Wine Tasting (a 5 minute walk!) Enjoy the view from the elegant patio while cooking/grilling, take a stroll through the vines, or a hike up the hill to enjoy the view from the hammocks.