Holiday houses in Dillard

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Top-rated holiday rentals in Dillard

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Guest favourite
The spacious studio layout features a modern design with a cozy seating area, a large television, and a dining space with multiple white chairs. A stone accent wall adds character, while natural light enters through the windows, illuminating the soft carpeting.
Apartment in Roseburg
4.95 out of 5 average rating, 148 reviews

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)

Top Guest favourite
A treehouse elevated 17 feet above the ground is surrounded by tall Douglas fir trees. A wooden staircase leads to the entrance, flanked by a wraparound deck. The exterior features warm wooden tones, and large windows offer glimpses of the forest.
Treehouse in Sutherlin
4.96 out of 5 average rating, 114 reviews

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.

Top Guest favourite
A cozy living area features two patterned chairs positioned near a wooden coffee table. A wall-mounted television displays artwork, while a decorative wall piece is visible. The space is adorned with a blue accent wall, wooden paneling, and a light fixture with multiple bulbs.
Home in Riddle
4.94 out of 5 average rating, 261 reviews

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.

Top Guest favourite
A living area is presented featuring a comfortable gray sofa, a wooden coffee table, and a flat-screen TV. Soft natural light enters through the window, highlighting the light hardwood flooring and a ceiling fan above. A decorative lamp and a wall clock add to the inviting ambiance.
Guesthouse in Myrtle Creek
5 out of 5 average rating, 116 reviews

Charming, quiet cottage near I-5

You'll be surrounded by peace and beauty in your private cottage in Myrtle Creek. Conveniently located under 2 miles from EXIT 108 on I-5 at the very end of a cul-de-sac in a family friendly neighborhood. 600-square feet and lots of natural light and tall ceilings. Beautiful hardwood floors throughout that were reclaimed from an Oregon high school gymnasium. We've spared nothing for your comfort. Please read our honest reviews! We know you'll love it here - and you might not want to leave!

Top Guest favourite
A cozy bedroom features a spacious bed adorned with a quilted cover and decorative pillows. A wooden tray with two mugs, a plate with snacks, and a small vase of flowers rests on the bed. Light streams in through two windows, highlighting the calming decor.
Cottage in Tenmile
5 out of 5 average rating, 153 reviews

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.

Top Guest favourite
A champagne flute filled with a light golden beverage is positioned on a wooden surface. The reflection of a sunset is visible in the glass, with soft hues of orange and pink blending into the landscape. Trees and mountains form a serene background.
Guesthouse in Roseburg
4.97 out of 5 average rating, 116 reviews

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.

Guest favourite
The exterior of the home is showcased, featuring a light-colored facade and a well-kept yard. Two palm trees stand prominently in front, alongside green shrubs. A gravel driveway is visible with vehicles nearby, and a wooden fence frames the property, providing a sense of privacy.
Home in Winston
4.9 out of 5 average rating, 114 reviews

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.

Top Guest favourite
The classic mid-century home is positioned atop a slight hill, offering expansive views of downtown Roseburg and surrounding landscapes. The exterior features a flat roof and a mix of stone and wood finishes. A deck extends from the entrance, framed by lush greenery.
Home in Roseburg
4.92 out of 5 average rating, 280 reviews

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.

Top Guest favourite
A serene aerial view captures the Main Umpqua River bordered by lush greenery and expansive fields. Nearby vineyards and farms stretch across the landscape, conveying a sense of tranquility in the heart of wine country.
Guest suite in Roseburg
4.99 out of 5 average rating, 231 reviews

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.

Guest favourite
A residential exterior view showcases a light blue house set against a clear sky. A mature tree with green foliage provides shade, while gravel landscaping enhances the area. The entrance is marked by simple wooden steps leading to the door.
Home in Roseburg
4.85 out of 5 average rating, 371 reviews

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!

Top Guest favourite
A cozy outdoor seating area features two wicker chairs adorned with colorful cushions. A modern fire pit sits between them, with a bottle of wine and two glasses ready for use. Lush greenery and garden views are visible in the background.
Guest suite in Roseburg
4.98 out of 5 average rating, 308 reviews

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.

Top Guest favourite
Home in Roseburg
5 out of 5 average rating, 238 reviews

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!

Popular amenities for Dillard holiday rentals

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