Vacation rentals in Dillard

4.94 out of 5 average rating, 125 reviews

A wooden cabinet with glass doors is filled with various personal care items. Shelves contain organized jars and packaged products, including bandages and toiletries. An illuminated nightlight featuring a scenic design is positioned below, adding soft light to the bathroom space.

Home in Riddle

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.

5 out of 5 average rating, 141 reviews

The image captures the Main Umpqua River, reflecting the surrounding trees and clouds. The water appears calm, showcasing a blend of greens and blues. Lush vegetation lines the riverbanks, contributing to the serene natural ambiance of the area.

Guest suite in Roseburg

Riverfront Hideaway - Hot Tub - Private Entrance

Kick back and relax in this calm, stylish space. While located in the heart of wine country with river views and river access only a few short steps away, it's still just a quick 10-minute jaunt into town. Fishing, agriculture, local activities, and wildlife surround our peaceful hideaway. We fell in love with this place! Come immerse yourself in its natural serenity. The unit is on 12+ acres and attached to the main house. It's been recently remodeled. Seasonal water sports available.

Vacation home in Days Creek

4.95 out of 5 average rating, 113 reviews

The Lookout •Complimentary Farm Breakfast

Part of the original homestead, The Lookout is in the fully remodeled Main Lodge Triplex. Nestled into the hillside, with sounds from the nearby creek, it's in the heart of an off grid working farm. This apartment features one bedroom, one bathroom, and a fully stocked kitchen. We also include our famous, you-cook breakfast with sausage and eggs produced here at the farm! The main living space has a futon that can fold down into a second bed, so this apartment comfortably sleeps 4.

4.98 out of 5 average rating, 161 reviews

Cottage in Myrtle Creek

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).

4.99 out of 5 average rating, 251 reviews

An outdoor patio area is presented, featuring a stone pathway leading to a gray wooden entrance door. A picnic-style table with attached benches sits on a gravel surface, surrounded by potted plants. A decorative 'RELAX' sign and an umbrella provide an inviting touch.

Guesthouse in Roseburg

The Bliss/amazing rates/walk to DT/food/wine/shops

Welcome to the Bliss! Crisp, clean, & ready for your arrival! Thoughtfully curated with high-end linnens & amenities, ensuring you feel pampered from the moment you arrive. Tucked behind our main residence, this private sanctuary provides a peaceful escape while keeping you close (2 blks down)to the vibrant energy of local restaurants, wineries, boutique shops, & the lively Sat farmers market. 9am-1pm hotsprings, falls, (1 hr)Crater lake (90 min)Wildlife safari (10 min)

4.94 out of 5 average rating, 167 reviews

A spacious recreational area features a green felt pool table, positioned centrally under a rustic metal ceiling. The room contains a comfortable seating area with a sofa, a wall-mounted television, and several antlers displayed decoratively. Natural light enters through a window adorned with dark curtains.

Guesthouse in Glide

Highway to Diamond Lake/Crater Lake roadtrip stop!

Relax and have some fun in our renovated 1 bed/1 bath detatched garage in our large fenced back yard. The space can sleep 6 people with a queen size bed, with queen and full size futon/sleepers. One block off highway 138, within minutes of a coffee shop, 3 restauraunts and a bar and grill. Single serve coffee maker, electric skillet, microwave, and a mini fridge. Pool/ping pong table, 55" smarttv, preloaded Nintendo, bluray player, and board games. Ask for wifi😊

4.96 out of 5 average rating, 158 reviews

A scenic view showcases a large lake surrounded by mountains, with a small island in the center. The water appears deep blue and clear, contrasting with the rocky shoreline and green tree-covered areas. Bright blue skies and distant peaks are visible in the background.

Camper/RV in Roseburg

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, a full bathroom, kitchen, refrigerator & microwave to help you feel at home as well as a designated easily accessible parking space.

A private balcony features a round table accompanied by two white chairs, surrounded by autumn foliage. Leaves are scattered on the wooden floor, enhancing the outdoor experience. A tranquil view of trees captures the peaceful ambiance of the setting.

4.83 out of 5 average rating, 292 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!

4.98 out of 5 average rating, 265 reviews

A charming pathway is framed by greenery, featuring potted plants along the sides. Sunlight casts patterned shadows onto the pebbled walkway, which leads toward a lattice gate in the distance. The walls are clad in blue shingles, hinting at a serene outdoor garden space.

Guest suite in Roseburg

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 spacious deck features two wooden chairs positioned around a gas firepit. Lush green fields and trees create a serene backdrop, with overcast skies above. The nature surrounding the deck invites relaxation and enjoyment of the outdoors.

4.99 out of 5 average rating, 138 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!

4.95 out of 5 average rating, 203 reviews

Tiny home in Riddle

The Circle C Guest House

Dan and Sally, hosts for 7+ years, invite you to stay at the newly rebuilt Circle C Guest House - a 288sf pet-friendly tiny home on the 9-acre Circle C Ranch 6 miles off I-5 Exit 103 (Riddle/Tri City), which is 22 miles south of Roseburg. Visit Umpqua valley wineries, Wildlife Safari, Cougar Canyon Golf Course and Seven Feathers Casino. Fishing, hunting, swimming, hiking and cycling opportunities nearby. Discounts for stays of 4 or more nights.

The guest house features a striking wooden exterior, with large glass doors framed by a covered porch. Sunlight shines brightly above, casting an inviting glow. Surrounding the house, lush vineyards and rolling hills create a scenic backdrop.

4.97 out of 5 average rating, 636 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.

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Popular amenities for Dillard vacation rentals

Kitchen

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Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Dillard

4.99 out of 5 average rating, 95 reviews

The log cabin features a spacious front porch with multiple wooden tables and chairs, surrounded by a gently sloping yard. Tall trees provide a natural backdrop, while a stone pathway leads from the grassy area to the cabin entrance.

Cabin in Roseburg

Firewater Lodge Log Cabin

MichelleRating, 5 stars1 week ago

This place is absolutely amazing!! everything you would need and so much more. so peaceful and quite. Beds are comfy to sleep in.

4.94 out of 5 average rating, 223 reviews

The exterior of Aviation Suites is visible with a large blue sign displaying its name. A private jet is parked on the tarmac, with a backdrop of partially cloudy skies. The building features a modern design, consistent with the business's aviation theme.

Guest suite in Roseburg

Aviation Suites: Flight Deck

CarlRating, 5 stars5 days ago

Loved the location and it was comfortable and roomy. We liked the big sitting area and watching the planes come in. Bottom floor was a plus.

Vineyards stretch across a lush landscape, with rows of grapevines leading towards a tranquil body of water. The backdrop features rolling hills under a clear blue sky, suggesting a serene rural setting. Sunlight casts a gentle glow over the scene, enhancing the greenery.

4.92 out of 5 average rating, 59 reviews

Sequoia Cottage

TroyRating, 5 stars1 week ago

We rented this home for the guest speakers for the weekend. They commented that the place was "perfect" for what they needed. The house was very welcoming and made them feel right at home. Great hostess, great communication, and great place!

4.96 out of 5 average rating, 98 reviews

Apartment in Roseburg

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

JoRating, 5 stars1 week ago

This place was absolutely gorgeous. Big beautiful windows opened out onto trees and gardens, outdoor spaces to relax. Karen was super responsive and friendly. Thanks so much!

4.97 out of 5 average rating, 29 reviews

A wooden treehouse elevated above the snowy ground is nestled among tall evergreen trees. A small deck with a railing is present, and access stairs lead up to the entrance. Snow covers the ground and branches, creating a serene winter scene.

Treehouse in Sutherlin

Mountain View Treehouse

JennaRating, 5 stars5 days ago

We had a great stay at this cool treehouse my son loved it we were surrounded by nature and saw deer and turkeys. We had a comfortable night the space is small and was perfect for our one night stay. We were also surprisingly close to town for dinner and breakfast too.

A metal welcome sign is displayed, featuring a campfire surrounded by two Adirondack chairs, flanked by mountains in the background. The words 'Big Rock Bunk House' are prominently engraved at the bottom, inviting guests to the property.

Guesthouse in Winston

5 out of 5 average rating, 3 reviews

Big Rock Bunk House

MatthewRating, 5 stars3 weeks ago

This was one of the most peaceful and bucolic places I have visited. Beautiful covered porch with outdoor chairs and tables to take it all in. I will book it again as soon as I can!~

5 out of 5 average rating, 76 reviews

A charming Highland calf stands on lush green grass. Its soft, wavy coat is a warm shade of brown, and its expressive eyes and distinctive horned features contribute to its endearing appearance. The backdrop of vibrant pasture enhances the serene ambiance of the farm.

Home in Myrtle Creek

Highlands and Horses Ranch

TarynRating, 5 stars3 days ago

Toni’s place was absolutely magical. Every little detail taken care of. Instructions on how everything works. Extra amenities if one forgot items from home. The house was very clean and so warm and inviting. On a very warm weekend it was nice to have air in the house. The screened in sun porch quickly became my favorite spot to sit in the morning with coffee and watch the sun rise. It exceeded our expectations. We will definitely return.