Holiday rentals in Roseburg

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)

Comfortable Modern Boho 2 bedroom downtown

Relax in this calm stylish space perfect for outdoor enthusiasts, business professionals & families. Located just steps from the courthouse, restaurants & more. This charming light-filled home has comfortable furnishings that can accommodate up to 4 people. Enjoy lots of natural light, soak in the claw foot tub or enjoy the private deck. The home is a short drive to fishing, hiking, wine tasting and the Wildlife Safari! You'll find the home to be comfortable with all the amenities you'll need.

Heavenly Bungalow, Immaculate, Guest Favorite

You will sleep well knowing that ALL linens are washed and entire home is cleaned thoroughly after each guest. This 2 queen bedroom vacation home is Ideally located off of I-5, a short distance to historic downtown Roseburg. This recently updated bungalow is charming and artfully decorated. 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.

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.

Charming 1927 English Cottage

Return to the roaring 20's when you enter this charming 1927 English Cottage in the Downtown Historic District of Roseburg, Oregon. Enjoy views of the city while relaxing in this cozy cottage furnished with mostly vintage furniture, décor & books. Even 1920's sheet music with Ukelele arrangements as well as a ukulele are provided for your enjoyment! Nestled in a quiet neighborhood of historic homes, you are within walking distance of some of Roseburg's finest restaurants, pubs & shops.

The Bliss/winter warm/total privacy/2 blks 2 DT

Welcome to The Bliss, a charming studio-style guestsuite, 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)

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.

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.

The Lookout PNW Roseburg Retreat

Escape to this serene, modern retreat featuring stunning views and a stylish design. The bright, open-concept kitchen and living area is perfect for relaxing, with large windows bringing nature inside. Enjoy your morning coffee on the spacious deck surrounded by trees, or unwind in the sleek, contemporary bathroom. The cozy bedrooms offer peaceful views, creating the perfect spot for a restful getaway. Whether you’re looking for comfort or adventure, this home has it all!

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.