Holiday houses in Winston

Hilltop View Apartment~ 2Bdrm, 1Bth, Full Kitchen

Welcome to Beulaire, our Mid Century Retreat overlooking Roseburg in the Beautiful Umpqua Valley. Our Suite is a 2 bedroom Guest Suite with its own private entrance, full kitchen and stunning views!! April and Paul, reside in the separate upstairs level while you enjoy your exclusive stay! Walk to Charming Downtown Roseburg discovering Dining, Breweries, Shopping & Salons. A short drive to the Beautiful Vinyard Loop & Crater Lake just 90 minutes away, down hwy 138...the hwy of waterfalls!

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

Sophisticated Bungalow, Walk Downtown, Immaculate

Our 2 bedroom vacation home is Ideally located off of I-5, within walking distance to downtown Roseburg. The Sophisticated Bungalow has recently been updated, enjoy the charming & artful decor. Relax in the cute private backyard or front covered porch. Whether you are visiting Roseburg, Umpqua Valley wine country, Crater Lake, the Oregon Coast, or just passing through on I-5. We provide all the amenities you need to feel as if you are home away from home. We treat our guest like family!

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.

OREGON HILLTOP RETREAT

Enjoy this large home in a secluded wooded setting with stunning views only 10 minutes from town. Perfect for family reunions, business retreats, friends' getaway, or anything your heart desires. The Umpqua Valley is a hidden jewel that offers many wineries, the Umpqua River for floating, fishing, and kayaking and Highway 138 with many waterfalls only steps away on your way to the beautiful Crater Lake. Or if you just need to get away from it all and relax this is your spot.

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.

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.

Camp 505-Little Cabin in the Woods Sunny Valley OR

Welcome to our charming rustic cabin nestled on 10 acres of breathtaking land in Beautiful Sunny Valley, Oregon! We are located less than a mile off I-5 and 10 miles north of Grants Pass,Oregon. This cozy retreat , offering a perfect blend of antique charm and modern comfort. Discover the wonders of our 10-acre property and the expansive outdoor space is perfect for picnics, stargazing, or sipping a glass of wine as you sit by the fire pit.

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.