Riddle Vacations from $474

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Your Riddle Vacation

With a vacation package to Riddle, say goodbye to endless planning and hello to hassle-free adventure. Every detail of your escape has been taken care of before you depart, so you can enjoy each moment discovering this vibrant city. Your trip to Riddle wouldn't be complete without checking out a few leading attractions, like Seven Feathers Casino. Whatever your travel plans or the size of your budget, putting together a tailored Riddle vacation is a piece of cake with Expedia.

The Latest Riddle vacation packages

Price found within the past 48 hours. Click for updated prices.
Paschal Winery

Paschal Winery

4.5 out of 5
Price was $575, price is now $474 per person
$474
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Medford (MFR)
9.8/10 Exceptional! (18 reviews)
Incredible experience, fabulous wine, wish we had stayed longer to soak in the beauty of the experience.

Reviewed on Apr 11, 2026

Wine Country Inn

Wine Country Inn

3 out of 5
Price was $638, price is now $477 per person
$477
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Medford (MFR)
9.4/10 Exceptional! (1,002 reviews)
Great location. Rooms are always very clean. Staff is very friendly. Very nice variety of quick pick up breakfast items.

Reviewed on Jun 1, 2026

The Orth House Inn by Remotion

The Orth House Inn by Remotion

3.5 out of 5
Price was $711, price is now $592 per person
$592
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Medford (MFR)
8.6/10 Excellent! (28 reviews)
It was a neat place. Bed was good. It’s an old place so modern touches weren’t really available. It’s really close to everything, which was great. The shower left a lot to be desired. This room is right where all the outdoor seating is for music, events, etc. so be prepared for people right outside your windows. Still a good place to stay.

Reviewed on May 20, 2026

Medford Home and 2 Condos With Pool

Medford Home and 2 Condos With Pool

2 out of 5
Price was $2,382, price is now $1,999 per person
$1,999
per person
Jul 5 - Jul 9
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Medford (MFR)
No reviews
Quail Run Mountain View Cottage

Quail Run Mountain View Cottage

2 out of 5
Price was $1,302, price is now $1,100 per person
$1,100
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Medford (MFR)
No reviews
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Riddle Hotel Deals

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 OR
$130 nightly
The price is $132 total per night from Jun 18 to Jun 19
$132 total
Jun 18 - Jun 19
Total with taxes and fees
9.8/10 Exceptional! (96 reviews)
"Kathie is one of those sweet, huggable people! We weren't able to check in until after 9pm, but she was so kind and accommodating, we felt as if we were staying with a family member Unfortunately we didn't get to spend any time enjoying the lovely setting, as we were gone all day for a reunion. We ..."

Reviewed on May 29, 2026

Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave Roseburg OR
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $118 total per night from Jun 3 to Jun 4
$118 total
Jun 3 - Jun 4
Total with taxes and fees
8.6/10 Excellent! (1,472 reviews)
"Absolutely awful experience at the Riverfront Inn in Roseburg. We were exhausted after a long drive and booked this hotel thinking it would be a safe, decent place to stay based on the 8.2/10 rating on Hotels.com. That rating is incredibly misleading. The moment we pulled in, there were cars blocking ..."

Reviewed on May 27, 2026

Riverfront Inn Roseburg
SureStay by Best Western Roseburg

SureStay by Best Western Roseburg

2.5 out of 5
2855 NW Edenbower Blvd Roseburg OR
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $109 total per night from Jun 3 to Jun 4
$109 total
Jun 3 - Jun 4
Total with taxes and fees
8/10 Very Good! (1,003 reviews)
"Good breakfast, weight room was nice"

Reviewed on Jun 1, 2026

SureStay by Best Western Roseburg
See all 85 properties in Riddle
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.

Find the Best Riddle Vacation Packages

Riddle Essential Information

Language
English
Currency
U.S dollars
Population
1,200
Top Sights
Pyrenees Vineyard & Cellars, Seven Feathers Casino and South Umpqua River

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Frequently asked questions

How much does a Riddle vacation package cost?
Offering excellent value package deals from $474 on Expedia, you'll be thrilled with how little a vacation to Riddle costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Riddle?
You can generally find reduced prices and better availability in October, November and December. Browse our cheap Riddle vacation packages and you could land some great off-season discounts.
How many days is enough for Riddle?
With a well-planned itinerary, you can easily hit the most popular Riddle sights in a handful of days. But if you prefer to venture off the beaten track or take day trips, consider booking your Riddle vacation for longer.
How to find the best Riddle package deals?
Use Expedia's filters to help you find some fabulous Riddle package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Riddle package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Riddle vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component separately. And you'll still have the freedom to create a tailored Riddle vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Riddle?
If you've got your Riddle travel dates finalized, book as soon as you can to grab some fantastic deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Riddle vacation packages?
Your Riddle getaway is meant to be a relaxing escape from your busy life, not a reason for money worries. So to allow you extra flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.