Holiday houses in Dillard

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Top-rated holiday rentals in Dillard

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Home in Riddle

4.9 out of 5 average rating, 134 reviews

Vintage Boho Bungalow in the South Umpqua Valley

Relax and enjoy your stay at our cozy 700 square foot cottage in the heart of historic Riddle OR. Everything you need for a comfortable visit is provided with a fully equipped kitchen and all amenities. The outdoor living area has a covered patio with fire pit and comfy chairs. There is a gas BBQ with outdoor dining under the shade of the walnut tree where the papasan swing is ready for relaxation. Pets are welcome! The front yard is fenced for privacy and will contain small & medium sized dogs.

29 June – 6 July

$1,419 AUD total

Guest favourite

Home in Roseburg

4.94 out of 5 average rating, 213 reviews

The Dr. J. R. Chapman Home

STEP BACK IN TIME…when you visit the J.R. Chapman house in the Downtown Historic District of Roseburg, Oregon. Built c.1903 by noted Dentist, Dr. John Russell Chapman, this Craftsman bungalow has an ambiance found only in homes with history. The home is furnished with mostly vintage decor. Located on 3/4 of an acre within walking distance of some of Roseburg’s finest restaurants, pubs, shops, the DC Courthouse & the Roseburg Library. We invite you to experience the charm of the Chapman house.

23 – 30 Nov

$1,593 AUD total

Guest favourite

Guesthouse in Roseburg

4.99 out of 5 average rating, 206 reviews

The Bliss/charismatic/big picture windows/AC

Welcome to the Bliss, your serene escape awaits! Picture yourself unwinding in our courtyard, on one of our sun loungers sheltered by a 15-foot umbrella. As the day turns to evening, indulge yourselves into the outdoor living room with ambient lighting, firepit, TV, curtains Those seeking a bit of playful diversion, will enjoy our Arcade/playoom Meanwhile, our variety of outdoor games, & picnic area. We are offering you a rejuvenating retreat that's both soothing and exhilarating.

7 – 14 Oct

$1,050 AUD total

Guest favourite

Campervan/RV in Roseburg

4.97 out of 5 average rating, 134 reviews

West Roseburg Hideaway

Our happy little camper is nestled in the Umpqua Valley surrounded by mountains, hiking trails, & waterfalls galore! Roseburg has many wineries & breweries to explore as well as coffee shops & great restauraunt options to choose from. We are located in a great neighboorhood with lots of walking & biking. There is a comfy queen bed with luxurious linens, a full bathroom, kitchen, refrigerator & microwave to help you feel at home as well as a designated easily accessible parking space.

6 – 13 Aug

$881 AUD total

Guest favourite

Cottage in Myrtle Creek

4.99 out of 5 average rating, 119 reviews

Rae of Sunshine Sanctuary

Come and enjoy a quiet and relaxing stay where you can put your feet up and unwind inside of our beautiful 100 year old quaint cottage, or enjoy the gorgeous private scenery and wildlife surrounding it. Many which include a variety of birds, deer, our residential goats, pig, horses, bunnies, and our seasonal pond with mallards and frogs. (All of our animals are located on the property but are separate from the cottage. Please see host about scheduling any interactions).

11 – 18 Apr

$1,292 AUD total

Guest favourite

Cottage in Roseburg

4.99 out of 5 average rating, 223 reviews

Bella's Cozy Cottage, Entire home with yard use

Our reviews say it all! We are guests favorite/super hosts. This sweet little 40's cottage is cozy and full of charm & period pieces.Just 1/4 mile off I-5 in a nice, quiet neighborhood. Very close to VA, bike path, shopping CTR, grocery stores ( Fred Meyers,Grocery Outlet), coffee, restaurants & fast foods. Close to Mercy Hos. Great location for day trips to the Oregon Coast, Crater/Diamond Lakes, fishing, boating, Umpqua Valley Wines, Golfing, WildLife Safari & more

20 – 27 Aug

$1,120 AUD total

Guest favourite

Guest suite in Roseburg

4.98 out of 5 average rating, 216 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.

14 – 21 Oct

$1,020 AUD total

Guest favourite

Guesthouse in Roseburg

4.94 out of 5 average rating, 172 reviews

Riverfront Flower Farm Retreat

Welcome to Rustic River Farms! Situated on 5.5 acres in wine country along the Umpqua River, our riverfront guest house offers a quaint, quarky space to unwind. During summer months you can take in the views of lavender and seasonal flowers in our field. We are also in the heart of some awesome fish runs. A perfect base camp for the fisherman or couples looking for a quiet retreat, which can also accommodate 1 adult or 2 children on the sleeper sofa.

10 – 17 Sept

$1,293 AUD total

Guest favourite

Guest suite in Roseburg

4.89 out of 5 average rating, 199 reviews

The Chadwick

Welcome to The Chadwick! This charming 1915 craftsman style home features a private queen size bedroom, private living room, kitchenette and private bathroom in the heart of Historic Downtown Roseburg. Just a few minutes off of the I5 freeway and highway 138 you are perfectly located for a quick rest stop or an extended stay in the stunning Umpqua Valley. Enjoy a complimentary tasting at Trella Vineyards, just 2 blocks from The Chadwick, on your host!

20 – 27 Oct

$1,129 AUD total

Guest favourite

Home in Roseburg

4.98 out of 5 average rating, 564 reviews

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.

14 – 21 Mar

$1,397 AUD total

Guest favourite

Guesthouse in Roseburg

4.95 out of 5 average rating, 144 reviews

Brandy Farms Country Cottage

Enjoy the beauty of Oregon in this charming cottage located in wine country. Farm setting within minutes from town. 10 Acres of Farmland and Fruit Trees to Explore Kitchen includes Dishwasher, Microwave, Stove, Toaster, Keurig, & Refrigerator Complimentary Tea, Coffee, Sparkling Water, & Snacks TV - Dish Network & Netflix Full Size Washer and Dryer Thermostat Control Heat & AC Luxurious Queen Bed

18 – 25 Jan

$1,593 AUD total

Guest favourite

Home in Winston

4.96 out of 5 average rating, 112 reviews

The Watusi Place - A Modern Umpqua Valley Getaway

Plan your getaway in the heart of Umpqua Valley! Welcome to The Watusi Place - a trendy, 3 bedroom/2 bath home just 0.5 miles from Abacela Winery and 1.5 miles from Wildlife Safari! With more than 30 wineries, 5 breweries , hiking/fishing/rafting just minutes away, this thoughtfully designed home is the perfect place to stay for exploring everything the Umpqua Valley area has to offer.

11 – 18 Aug

$2,828 AUD total