Holiday rentals in Umpqua

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!

Serene Escape Studio (with w/d, a/c, kitchen)

Forget your worries in this spacious and serene space. With over 800 square feet, this newly designed studio apt located in a quiet neighborhood has everything you need to make your stay in centrally located Roseburg a success--washer/dryer, kitchen, large screen tv, etc. Once parked, traverse through the gate, up the stairs to your private entrance off the upper deck. Perfectly located for day trips to the coast, Oregon's waterfalls, Crater Lake National Park, and more! (Note: we do have dogs)

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.

Sutherlin Retreat with a View & Wildlife w/brkfast

Experience wine country by touring our Douglas County vineyards. Come back and stay in our comfortable 1-bdrm w/queen bed, 1-bath apartment; a full-size hideabed; complete kitchen; living room w/big screen TV and sofa. With advance notice, we'll bring in a PacNPlay, if needed. Enjoy a dip in the pool from June thru Sept. Some breakfast materials will be in the fridge to prepare at your leisure during your stay. Free wine tasting for 2 at Reustle Winery Mon-Sat with stay (you reserve).

The Wine Room, Oakland OR

Need a quiet, quaint refuge with cozy modern amenities? The Wine Room is in the small town of Oakland Oregon. Umpqua Valley one hour south of Eugene. It is safe while just a mile off of I-5. Walk the uncrowded town and parks. For longer stays your use of the kitchen Is negotiable. The private room has a beautiful bathroom with a heated floor, a mini-fridge and micro. Located in the back of a historic bank building that is our tasting room and coffee shop it is good for couples and solo.

The Bliss/100% privacy/game room/2 blks 2 DT

Welcome to The Bliss, a charming studio-style guesthouse, designed for relaxation, comfort, and a little bit of magic. Tucked quietly behind our home, this private retreat offers the perfect blend of rustic character and chic style—just two blocks from downtown. Whether you’re here for a weekend escape, wine tasting, or a peaceful reset. The Bliss is a place where guests instantly feel spoiled, relaxed, and well cared for. Waterfalls, (1 hr)Crater lake (90 min)Wildlife safari (10 min)

Chic RV Retreat, Stunning Yard in Roseburg

Welcome to the Roseburg Relax Inn, a modern retreat nestled in a serene backyard oasis. Our sleek 2024 RV offers a perfect blend of contemporary comfort and outdoor charm, ideal for families, couples, or solo adventurers. With stylish interiors, a lush outdoor space, and all the modern amenities you need, this is more than just a stay—it’s a tranquil escape waiting for you. If you're craving a getaway that combines luxury with nature, Roseburg Relax Inn is the perfect choice.

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.

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)

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!

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.