Riddle Vacation Rentals

Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Riddle vacation rentals

Property grounds

Condo in Riddle

Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
9.8 out of 10, Exceptional, (90 reviews)
"My wife and I travel a lot with our little dachshund. This property is one of the nicest private offerings we have ever experienced. The owner has created a perfectly lovely and cozy little apartment for two. It is completely stocked and meticulously well-organized. The owner is also gracious and very flexible. An ideal place to stay."
United States
Dale
$145 nightly
The price is $147
Feb 27 - Feb 28
Total with taxes and fees
Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
Terrace/patio

Vacation Home in Douglas County

Blissful Solitude Cottage
10.0 out of 10, Exceptional, (6 reviews)
"It is a nice place to stay"
United States
Matthew O.
$173 nightly
The price is $175
Mar 1 - Mar 2
Total with taxes and fees
Blissful Solitude Cottage
Smart TV, fireplace, books, music library

Vacation Home in Roseburg

Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort
9.8 out of 10, Exceptional, (39 reviews)
"We had a great stay while we visited family. The house had everything we needed, and the new mattresses were very comfortable. Gary was easy to get ahold of and responded quickly. We would stay again. "
United States
Riley E.
$279 nightly
The price is $305
Mar 2 - Mar 3
Total with taxes and fees
Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort
Outdoor dining

Cabin in Azalea

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
9.4 out of 10, Exceptional, (22 reviews)
"Wonderful and peaceful place to stay! Breakfast accommodations were above and beyond and such a pleasant surprise! Highly recommend this cute place!"
United States
Connie H.
$300 nightly
The price is $305
Mar 2 - Mar 3
Total with taxes and fees
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Exterior

Vacation Home in Roseburg

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
9.8 out of 10, Exceptional, (92 reviews)
"We had a great stay! The house was amazing, and peaceful. We would definitely stay again. "
United States
Ashley D.
$190 nightly
The price is $208
Feb 28 - Mar 1
Total with taxes and fees
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Terrace/patio

Vacation Home in Douglas County

Orchard House, Orchard House Retreat
10.0 out of 10, Exceptional, (1 review)
"Fantastic place to spend the holiday very serene very peaceful"
United States
Gin H.
$195 nightly
The price is $197
Mar 1 - Mar 2
Total with taxes and fees
Orchard House, Orchard House Retreat
Property grounds

Camping in Douglas County

Starry Skies Campout
$83 nightly
The price is $84
Mar 1 - Mar 2
Total with taxes and fees
Starry Skies Campout
Exterior

Vacation Home in Roseburg

The Urban Boho Charmer with Private Backyard, BBQ & Hammock
9.6 out of 10, Exceptional, (38 reviews)
"Nice place, great location."
United States
Gordon
$209 nightly
The price is $229
Mar 1 - Mar 2
Total with taxes and fees
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Property grounds

Cottage in Myrtle Creek

Charming, Private Cottage near I-5 and Golf Course.
10.0 out of 10, Exceptional, (43 reviews)
"This is the second time I have stayed here, both times with my dog. The place is convenient, quiet, clean, comfortable, and with great touches and landscaping outside. Wonderful place."
United States
Carter L.
$191 nightly
The price is $191
Mar 5 - Mar 6
Total with taxes and fees
Charming, Private Cottage near I-5 and Golf Course.
Exterior

Vacation Home in Roseburg

Downtown Stay at the Red Tiny Twin!
9.8 out of 10, Exceptional, (23 reviews)
"It was a perfect place for us to stay for a short trip to visit family with our two little dogs."
United States
Rochelle S.
$156 nightly
The price is $170
Feb 27 - Feb 28
Total with taxes and fees
Downtown Stay at the Red Tiny Twin!
Exterior detail

Vacation Home in Roseburg

Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
9.6 out of 10, Exceptional, (29 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.
$180 nightly
The price is $197
Feb 27 - Feb 28
Total with taxes and fees
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Exterior detail

Vacation Home in Roseburg

Downtown Stay at the Blue Tiny Twin
9.4 out of 10, Exceptional, (19 reviews)
"Just the right size and location for a wine country getaway weekend. Had everything we needed, and more. Will not hesitate to book again next trip, if it's available."
United States
John L.
$165 nightly
The price is $181
Mar 21 - Mar 22
Total with taxes and fees
Downtown Stay at the Blue Tiny Twin
Dining

Vacation Home in Winston

The Watusi Place - A Modern Umpqua Valley Getaway
10.0 out of 10, Exceptional, (49 reviews)
"Home was well stocked and was very accessible to our winery we belong to. "
United States
Amy W.
$333 nightly
The price is $361
Feb 28 - Mar 1
Total with taxes and fees
The Watusi Place - A Modern Umpqua Valley Getaway
Smart TV

Vacation Home in Roseburg

Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
9.6 out of 10, Exceptional, (53 reviews)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
$165 nightly
The price is $181
Feb 27 - Feb 28
Total with taxes and fees
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Terrace/patio

Vacation Home in Roseburg

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
10.0 out of 10, Exceptional, (24 reviews)
"Absolutely the most delightful and magical place to stay! Wonderfully gracious hosts! They made our honeymoon stay spectacular and special! James and Gail are fabulous. We had the most incredible breakfast as well. We felt like royalty! "
United States
Rachel S.
$222 nightly
The price is $243
Mar 1 - Mar 2
Total with taxes and fees
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Exterior

Apartment in Wolf Creek

Cozy Historic Cabin Near Hiking
9.0 out of 10, Wonderful, (14 reviews)
"It would be perfect for someone trying to escape the business of city life or someone who needs total peace and quiet! The room and home are old but nicely decorated the grounds are beautiful and the people are friendly. I didn’t realize just how remote it was until I arrived and that made me feel somewhat uneasy the girls also were bored but if I needed some time to myself and rest it was perfect!"
United States
Shelley P.
$225 nightly
The price is $228
Feb 27 - Feb 28
Total with taxes and fees
Cozy Historic Cabin Near Hiking
Dining

Cottage in Winston

Charming cottage studio in serene environment perfect for a relaxing getaway
$180 nightly
The price is $183
Feb 27 - Feb 28
Total with taxes and fees
Charming cottage studio in serene environment perfect for a relaxing getaway
Property grounds

Mobile Home in Douglas County

Madrone Hideout, Madrone Hideout Chariot
$210 nightly
The price is $212
Mar 1 - Mar 2
Total with taxes and fees
Madrone Hideout, Madrone Hideout Chariot
Deluxe Apartment, City View | Private kitchen

Aparthotel in Roseburg

Bell Sister Flats
2.0 star property
$371 nightly
The price is $407
Mar 4 - Mar 5
Total with taxes and fees
Bell Sister Flats
Outdoor dining

Vacation Home in Roseburg

Private bungalow with AC in charming Roseburg
$347 nightly
The price is $352
Feb 27 - Feb 28
Total with taxes and fees
Private bungalow with AC in charming Roseburg
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

Motel 6 Roseburg, OR

Motel 6 Roseburg, OR

10/10 Excellent
"Excellent "
Matthew 2-night trip
Posted 2 days ago
Motel 6 Roseburg, OR

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.

Explore a world of travel with Expedia

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?


~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath: This vacation home near Riddle offers a selection of games, a barbecue grill, and air-conditioning to help you feel perfectly comfortable 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.