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Riddle Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Riddle vacation rentals

A garden with a wooden deck, a small shed, and a stone pathway.

1. Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly

Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
Riddle
9.8 out of 10, Exceptional, (102 reviews)
"Wonderful stay, peaceful and relaxing, exceptional host, highly recommended "
United States
Brad
$130 nightly
The price is $132
Oct 13 - Oct 14
Total with taxes and fees
Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
A wooden pathway leading to a covered area with a view of a mountainous landscape.

2. Charming, Private Cottage near I-5 and Golf Course.

Charming, Private Cottage near I-5 and Golf Course.
Myrtle Creek
10.0 out of 10, Exceptional, (50 reviews)
"We only had one night to stay here but it is one we would definitely stay at again. It was clean, bright, stocked with everything needed (no oven or range top but did have a toaster oven). It was very comfortable for us and our 2 dogs and very charming. We really enjoyed our quick visit. The only thing that could be an issue was there was a lot of steps to get down to the house which could be an issue for those with any mobility problems. The steps light up as you use them at night which was...
United States
cynthia
$200 nightly
The price is $200
Oct 11 - Oct 12
Total with taxes and fees
Charming, Private Cottage near I-5 and Golf Course.
A modern kitchen with stainless steel appliances, a wooden dining table, and a tufted ottoman.

3. Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
10.0 out of 10, Exceptional, (1 review)
"Beautiful flat! We loved our time there"
United States
Daniel
$420 nightly
The price is $460
Oct 12 - Oct 13
Total with taxes and fees
Bell Sister Flats
A cabin with a wooden deck, a picnic table, and a bench.

4. Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Azalea
9.4 out of 10, Exceptional, (28 reviews)
"Everything was good."
United States
Ginger C.
$305 nightly
The price is $310
Oct 4 - Oct 5
Total with taxes and fees
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
A wooden deck with a white railing, a potted plant, and a table.

5. Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Roseburg
10.0 out of 10, Exceptional, (25 reviews)
"Beautiful property and incredible stay. Not only was the room clean, private and super comfortable, the hosts were amazing. They made my comfort a priority every day! Definitely would give it a 5 star rating, I will recommend it to family and friends."
United States
Betty W.
$222 nightly
The price is $243
Nov 1 - Nov 2
Total with taxes and fees
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
A bathroom with a shower curtain, a towel rack, a water heater, and a striped towel.

6. Elk Meadow Hideaway LLC Minutes away Worlds apart

Elk Meadow Hideaway LLC Minutes away Worlds apart
Myrtle Creek
$128 nightly
The price is $130
Oct 4 - Oct 5
Total with taxes and fees
Elk Meadow Hideaway LLC Minutes away Worlds apart
A spacious living area with a wooden dining table, black chairs, a ceiling fan, and a television displaying a beach scene.

7. The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (59 reviews)
"Clean, fully updated, great location! The Wildlife Safari was a lot of fun, just 2min away. Easy drive to Crater Lake, a must-see. Great property!"
United States
Jason W.
$357 nightly
The price is $387
Oct 5 - Oct 6
Total with taxes and fees
The Watusi Place - A Modern Umpqua Valley Getaway
A small, single-story house with a green door, white trim, and a small porch.

8. The Urban Boho Charmer with Private Backyard, BBQ & Hammock

The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Roseburg
9.6 out of 10, Exceptional, (45 reviews)
"Nice place, great location."
United States
Gordon
$211 nightly
The price is $231
Oct 4 - Oct 5
Total with taxes and fees
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
A room with a large window, a black and white patterned rug, and a black chair with a plant.

9. Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher

Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher
Myrtle Creek
10.0 out of 10, Exceptional, (3 reviews)
"The Ranch was everything you could ever want and more it was the most quiet and peaceful night my wife was over the moon with the cows there definitely will be more stays in the future"
United States
Unspecified U.
$222 nightly
The price is $225
Oct 4 - Oct 5
Total with taxes and fees
Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher
A house with a covered porch, a seating area with a sofa and armchair, and a small table.

10. <br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Roseburg
9.8 out of 10, Exceptional, (117 reviews)
"The house worked perfectly for our needs! Its location made it easy to every thing that we needed."
United States
Sharon K.
$192 nightly
The price is $210
Oct 6 - Oct 7
Total with taxes and fees
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
A modern house with a stone pathway leading to the entrance, surrounded by various plants and a large planter.

11. Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Roseburg
9.6 out of 10, Exceptional, (32 reviews)
"Finding the entry to the property was hardest part. Parking was OK. The views and the space was great. Nice central location for many places to visit."
United States
Nicole B.
$182 nightly
The price is $199
Oct 4 - Oct 5
Total with taxes and fees
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
A red deck with two Adirondack chairs and a stone fire pit in a forest setting.

12. Orchard House, Orchard House Retreat

Orchard House, Orchard House Retreat
Douglas County
10.0 out of 10, Exceptional, (3 reviews)
"Great little well needed romantic getaway!"
United States
Shawn M.
$211 nightly
The price is $213
Oct 20 - Oct 21
Total with taxes and fees
Orchard House, Orchard House Retreat
A rustic lodge with a central entrance, multiple windows, and a stone pathway leading to a seating area.

13. Cozy Historic Cabin Near Hiking

Cozy Historic Cabin Near Hiking
Wolf Creek
9.2 out of 10, Wonderful, (16 reviews)
"We really enjoyed our stay. The place is comfy and just what we needed for our one night in the area. The host was great and easy to communicate with. The waffles were wonderful."
United States
Heather W.
$245 nightly
The price is $249
Oct 19 - Oct 20
Total with taxes and fees
Cozy Historic Cabin Near Hiking
Enjoy connecting around the porch firepit!

14. Blissful Solitude Cottage

Blissful Solitude Cottage
Douglas County
10.0 out of 10, Exceptional, (8 reviews)
"It is a nice place to stay"
United States
Matthew O.
$217 nightly
The price is $220
Oct 13 - Oct 14
Total with taxes and fees
Blissful Solitude Cottage
A wooden deck with a table and chairs, surrounded by a wire fence and string lights.

15. Camp 505 - Little Cabin in the Woods Sunny Valley Oregon

Camp 505 - Little Cabin in the Woods Sunny Valley Oregon
Wolf Creek
10.0 out of 10, Exceptional, (27 reviews)
"Lovely place to stay, clean and welcoming! "
United States
Nicole B.
$137 nightly
The price is $139
Oct 4 - Oct 5
Total with taxes and fees
Camp 505 - Little Cabin in the Woods Sunny Valley Oregon
A forest campsite with a bus, a blanket, and a bench.

16. Madrone Hideout-Artist Bus Retreat at Azalea Grove Getaway

Madrone Hideout-Artist Bus Retreat at Azalea Grove Getaway
Douglas County
10.0 out of 10, Exceptional, (1 review)
"Absolutely lovely little gem in the woods. Next time I hope to stay more than one night. For light sensitive people, there is a skylight over the bed and an early morning sunrise means seriously bright light."
United States
Pat B.
$192 nightly
The price is $194
Oct 4 - Oct 5
Total with taxes and fees
Madrone Hideout-Artist Bus Retreat at Azalea Grove Getaway
A compact room with a sofa, a small table, a bench, a door leading outside, and a ceiling fan.

17. Charming Garden Cottage with 155-Acre Forest Retreat Near Wolf Creek, Oregon

Charming Garden Cottage with 155-Acre Forest Retreat Near Wolf Creek, Oregon
Wolf Creek
$222 nightly
The price is $222
Oct 4 - Oct 5
Total with taxes and fees
Charming Garden Cottage with 155-Acre Forest Retreat Near Wolf Creek, Oregon
A modern kitchen with stainless steel appliances, a wooden dining table, and a tufted ottoman.

18. Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
10.0 out of 10, Exceptional, (3 reviews)
"Bell Sister Flats is amazing - so gorgeous, warm and inviting. We loved being on Main Street and walking to coffee, dinner, drinks. So much attention to detail and such comfort provided from the bed to the sheets to the towels and love seat and, oh the shower! Terry and Paul were wonderful hosts, so attentive and generous. Loved that they promoted the local community with goods and services in the flat. Loved our stay!"
United States
Tara T.
$331 nightly
The price is $362
Oct 12 - Oct 13
Total with taxes and fees
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
A small house with a porch and string lights.

19. Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (29 reviews)
"Close to downtown, well appointed, clean and comfortable. Thanks for a lovely stay!"
United States
Sue S.
$151 nightly
The price is $165
Oct 7 - Oct 8
Total with taxes and fees
Downtown Stay at the Red Tiny Twin!
A campfire with white chairs and a wicker chair around it, set in a forested area.

20. Starry Skies Campout

Starry Skies Campout
Douglas County
$83 nightly
The price is $84
Oct 4 - Oct 5
Total with taxes and fees
Starry Skies Campout
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Riddle Hotel Reviews

The Lodge at Roseburg

The Lodge at Roseburg

8/10 Good
"Great location off the hwy. clean rooms. I’d stay there again"
David 1-night trip
Posted 6 hours ago
The Lodge at Roseburg

Find out more about Riddle

Everything you need to know about Riddle vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Riddle vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Riddle vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Riddle vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Riddle. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Riddle in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $84 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Riddle rentals

At Expedia, we put the best Riddle vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Riddle rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Riddle vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Riddle. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Riddle?

Yes, you can find vacation rentals near popular attractions in Riddle, or you can select a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental that Riddle has to offer?

The Urban Boho Charmer with Private Backyard, BBQ & Hammock: This vacation home rental near Riddle is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Riddle?

Explore the area and family-friendly sights such as Wildlife Safari, or get out into nature at a spot like South Umpqua River. In the larger area, you’ll find Seven Feathers Casino and Douglas County Museum of History and Natural History.

What’s a vacation rental in Riddle like?

A vacation rental is a private property where you can stay for a long or short time in Riddle. Vacation rentals feature amenities like laundry facilities and kitchens so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for small groups.