Holiday houses in Dillard

4.94 out of 5 average rating, 125 reviews

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

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.

Holiday home in Days Creek

4.95 out of 5 average rating, 114 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

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

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

Campervan/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.

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

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.

4.99 out of 5 average rating, 139 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.

4.97 out of 5 average rating, 637 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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Other great holiday rentals in Dillard

4.99 out of 5 average rating, 95 reviews

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

Guest suite in Roseburg

Aviation Suites: Flight Deck

CarlRating, 5 stars6 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.

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

Treehouse in Sutherlin

Mountain View Treehouse

JennaRating, 5 stars6 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.

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, 77 reviews

Home in Myrtle Creek

Highlands and Horses Ranch

TarynRating, 5 stars4 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.