Riddle Vacations from $293

Book a Hotel + Flight or Car together to unlock savings

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.
Clarion Pointe Medford

Clarion Pointe Medford

2.5 out of 5
Price was $422, price is now $293 per person
$293
per person
Feb 13 - Feb 17
found 5 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Medford (MFR)
8/10 Very Good! (1,077 reviews)
Didn’t make my reservation. Plane flight got cancelled

Reviewed on Dec 9, 2025

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
Price was $590, price is now $428 per person
$428
per person
Feb 13 - Feb 17
found 5 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Medford (MFR)
9.6/10 Exceptional! (1,003 reviews)
Friendly staff. Upbeat atmosphere. Clean. Nice happy hour.

Reviewed on Nov 27, 2025

Hummingbird Estate Wine & Suites

Hummingbird Estate Wine & Suites

4.5 out of 5
Price was $624, price is now $475 per person
$475
per person
Feb 13 - Feb 17
found 5 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Medford (MFR)
9.6/10 Exceptional! (145 reviews)
We had an amazing stay at the Hummingbird Estate. The staff was so welcoming and our room was so cozy. Definitely will be back!

Reviewed on Dec 9, 2025

Paschal Winery

Paschal Winery

4.5 out of 5
Price was $519, price is now $407 per person
$407
per person
Feb 13 - Feb 17
found 5 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Medford (MFR)
9.6/10 Exceptional! (13 reviews)
It is a beautiful property. We stayed in the little trailer, glamp cottage and it was so cute. Also enjoyed the private hot tub provided. We did some wine tasting, a flight of white and a flight of reds and enjoyed their fabulous cork and fork dinner. The location is beautiful. My travelling companion said if she didn’t know better she would think she was in Switzerland.

Reviewed on May 3, 2025

Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
Price was $471, price is now $371 per person
$371
per person
Feb 13 - Feb 17
found 5 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Medford (MFR)
9/10 Wonderful! (2,611 reviews)
All of the above front desk were very helpful 👌 thank you for your assistance and help see you again soon

Reviewed on Dec 12, 2025

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Riddle Hotel Deals

Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly

Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly

Riddle OR
$125 nightly
The price is $127 total per night from Dec 23 to Dec 24
$127 total
Dec 23 - Dec 24
Total with taxes and fees
9.8/10 Exceptional! (82 reviews)
Yes it was all GREAY!!!

Reviewed on Nov 16, 2025

Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly
Holiday Inn Express Roseburg by IHG

Holiday Inn Express Roseburg by IHG

2.5 out of 5
375 Harvard Blvd Roseburg OR
Fully refundable
$101 nightly
The price is $111 total per night from Dec 28 to Dec 29
$111 total
Dec 28 - Dec 29
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
The place was nice and clean. The breakfast was varied enough for all people. I would stay there again.

Reviewed on Dec 7, 2025

Holiday Inn Express Roseburg by IHG
Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave Roseburg OR
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $101 total per night from Dec 14 to Dec 15
$101 total
Dec 14 - Dec 15
Total with taxes and fees
8.4/10 Very Good! (1,418 reviews)
I’ve stayed here plenty of times and I have never been disappointed. Always friendly and welcoming. Clean rooms and a great staff

Reviewed on Dec 1, 2025

Riverfront Inn Roseburg
See all 87 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 $293 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.