Riddle Vacations from $369

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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.
Arden Forest Inn

Arden Forest Inn

4 out of 5
Price was $431, price is now $369 per person
$369
per person
Jan 12 - Jan 15
found 4 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Medford (MFR)
9.8/10 Exceptional! (102 reviews)
Comfortable and close to downtown. Even though some reviews and the map say there is breakfast; there is none.

Reviewed on Nov 8, 2025

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
Historic Downtown District
Price was $544, price is now $449 per person
$449
per person
Jan 12 - Jan 15
found 4 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Medford (MFR)
9.2/10 Wonderful! (1,000 reviews)
We enjoyed our visit immensely. The room isn’t designed for someone who wants to work from their room, but it was perfect for a vacation. The room was beautiful, the service was great, the restaurant was delicious. We were blocks from the Shakespeare festival and steps from several great restaurants and amazing shops.

Reviewed on Dec 7, 2025

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Price was $502, price is now $422 per person
$422
per person
Jan 12 - Jan 15
found 4 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Medford (MFR)
9.2/10 Wonderful! (574 reviews)
The room and the breakfast. The staff were very nice.

Reviewed on Nov 23, 2025

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
Price was $461, price is now $405 per person
$405
per person
Jan 12 - Jan 15
found 4 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Medford (MFR)
9/10 Wonderful! (1,497 reviews)
Have stayed here o/n en route for several years. Room tired, clean. Carpets ripped. Accommodated our request for ground floor room. Disappointed that breakfast is no longer included.

Reviewed on Dec 9, 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
$95 nightly
The price is $105 total per night from Dec 20 to Dec 21
$105 total
Dec 20 - Dec 21
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 $369 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.