Riddle Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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, (104 reviews)
"I loved the mother in law unit with supplied kitchen, microwave, frig., etc, etc. The host is vary gracious and friendly. A quiet stay is why I really like it."
United States
Dixie
The price is CA $113
CA $182 total
includes taxes & fees
Nov 22 - Nov 23
Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
A dining area with a round table, white chairs, and a view of greenery through large windows.

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)
"Such a great little cottage prefect for a weekend trip to see family."
United States
Darla S.
The price is CA $233
CA $251 total
includes taxes & fees
Nov 11 - Nov 12
Charming, Private Cottage near I-5 and Golf Course.
A small cabin with a sloped roof, a wooden picnic table, and a string of lights.

3. Elk Meadow Hideaway LLC Minutes away Worlds apart

Elk Meadow Hideaway LLC Minutes away Worlds apart
Myrtle Creek
The price is CA $177
CA $196 total
includes taxes & fees
Dec 7 - Dec 8
Elk Meadow Hideaway LLC Minutes away Worlds apart
Enjoy connecting around the porch firepit!

4. 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.
The price is CA $132
CA $236 total
includes taxes & fees
Nov 11 - Nov 12
Blissful Solitude Cottage
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, (28 reviews)
"Our hosts, James and Gail, are so lovely. They really care about their guests experience and I felt they truly cared about our experience. It’s a gorgeous home that they have decorated meticulously, and made so comfortable for guests to enjoy. The bed was super comfy and the room cozy. The bedding and towels were soft and top notch. They didn’t skimp on anything. Gail is a great cook and provided homemade food, snacks, and drinks. Some items came from her garden. James is a master with sound and...
United States
Susan
The price is CA $263
CA $309 total
includes taxes & fees
Nov 11 - Nov 12
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
A forest setting with two people sitting on chairs, a fire pit, and a cooler.

6. 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.
The price is CA $132
CA $251 total
includes taxes & fees
Nov 11 - Nov 12
Madrone Hideout-Artist Bus Retreat at Azalea Grove Getaway
A red deck with two Adirondack chairs and a stone fire pit in a forest setting.

7. 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.
The price is CA $132
CA $251 total
includes taxes & fees
Nov 11 - Nov 12
Orchard House, Orchard House Retreat
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
The price is CA $176
CA $308 total
includes taxes & fees
Nov 13 - Nov 14
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
A cabin with a wooden deck, a picnic table, and a bench.

9. Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Azalea
9.4 out of 10, Exceptional, (29 reviews)
"Cookie sheets for kitchen would be the only thing we needed throughout the stay. If you are looking for a place to disconnect, this is the place to book!"
United States
Katie
The price is CA $215
CA $374 total
includes taxes & fees
Nov 11 - Nov 12
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
A living room with a sofa, coffee table, and a painting on the wall.

10. Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.6 out of 10, Exceptional, (22 reviews)
"Everything you need is in this small but efficiently planned house. The very small countertop dishwasher is so cute! Perfect place for solo or couple to stay."
United States
Beth B.
The price is CA $127
CA $235 total
includes taxes & fees
Dec 1 - Dec 2
Downtown Stay at the Blue Tiny Twin
A small house with a porch and string lights.

11. Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (31 reviews)
"Close to downtown, well appointed, clean and comfortable. Thanks for a lovely stay!"
United States
Sue S.
The price is CA $114
CA $221 total
includes taxes & fees
Nov 11 - Nov 12
Downtown Stay at the Red Tiny Twin!
A modern kitchen with stainless steel appliances, a wooden dining table, and a tufted ottoman.

12. 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
The price is CA $445
CA $596 total
includes taxes & fees
Nov 11 - Nov 12
Bell Sister Flats
A spacious living area with a wooden dining table, black chairs, a ceiling fan, and a television displaying a beach scene.

13. The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (60 reviews)
"Great place for us and the kids after a long day at the wildlife safari!"
United States
Jessica M.
The price is CA $229
CA $495 total
includes taxes & fees
Nov 11 - Nov 12
The Watusi Place - A Modern Umpqua Valley Getaway
A room with a large window, a black and white patterned rug, and a black chair with a plant.

14. 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.
The price is CA $240
CA $301 total
includes taxes & fees
Nov 11 - Nov 12
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.

15. <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, (120 reviews)
"Great stay, very clean. Would stay here again."
United States
Cindan G.
The price is CA $169
CA $283 total
includes taxes & fees
Nov 13 - Nov 14
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
A wooden deck with a table and chairs, surrounded by a wire fence and string lights.

16. 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, (28 reviews)
"Lovely place to stay, clean and welcoming! "
United States
Nicole B.
The price is CA $165
CA $185 total
includes taxes & fees
Nov 15 - Nov 16
Camp 505 - Little Cabin in the Woods Sunny Valley Oregon
A modern house with a stone pathway leading to the entrance, surrounded by various plants and a large planter.

17. 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, (33 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.
The price is CA $155
CA $257 total
includes taxes & fees
Nov 16 - Nov 17
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
A rustic lodge with a central entrance, multiple windows, and a stone pathway leading to a seating area.

18. Cozy Historic Cabin Near Hiking

Cozy Historic Cabin Near Hiking
Wolf Creek
9.2 out of 10, Wonderful, (17 reviews)
"Great place, super hosts, wonderful hikes in the area, and quiet and secluded."
United States
Roy R.
The price is CA $222
CA $305 total
includes taxes & fees
Nov 11 - Nov 12
Cozy Historic Cabin Near Hiking
A campfire with white chairs and a wicker chair around it, set in a forested area.

19. Starry Skies Campout

Starry Skies Campout
Douglas County
The price is CA $89
CA $107 total
includes taxes & fees
Nov 11 - Nov 12
Starry Skies Campout
A modern kitchen with stainless steel appliances, a wooden dining table, and a tufted ottoman.

20. 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.
The price is CA $309
CA $464 total
includes taxes & fees
Nov 11 - Nov 12
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
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

A hotel with a modern design, featuring a covered entrance, multiple floors, and a prominent sign.
Holiday Inn Express & Suites Roseburg North by IHG

Holiday Inn Express & Suites Roseburg North by IHG

Holiday Inn Express & Suites Roseburg North by IHG
Roseburg

10/10 Excellent

The property is very new and we liked the decor. Pool and gym very nice. Staff friendly and helpful
Canada
Richard
Reviewed October 31, 2026
Holiday Inn Express & Suites Roseburg North by IHG

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Riddle vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Riddle vacation rentals we have selected for you start as low as CA $88 per night. Entering your travel dates in the search wizard 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.