Riddle Vacations from $391

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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.
Wolf Creek Inn & Tavern

Wolf Creek Inn & Tavern

2 out of 5
Price was $475, price is now $391 per person
$391
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Medford (MFR)
9.4/10 Exceptional! (449 reviews)
Unique historic site operated by Oregon State Parks, lovely grounds around the Inn, restful and relaxed.

Reviewed on Jun 12, 2026

A Cowslip's Belle Inn

A Cowslip's Belle Inn

3 out of 5
Price was $1,064, price is now $834 per person
$834
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Ontario Intl. Airport (ONT) to Medford (MFR)
9.6/10 Exceptional! (45 reviews)
Lovely hidden gem in Ashland, walking distance to great restaurants and the Oregon Shakespeare Festival. Wonderfully welcoming host and lovely grounds to help you relax.

Reviewed on Jun 9, 2026

Wine Country Inn

Wine Country Inn

3 out of 5
Price was $582, price is now $457 per person
$457
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Medford (MFR)
9.4/10 Exceptional! (1,008 reviews)
My only complaint- $25 early check-in when there were clearly rooms available. That is not customer friendly!

Reviewed on Jun 17, 2026

Riverside Inn

Riverside Inn

2.5 out of 5
Price was $645, price is now $525 per person
$525
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Medford (MFR)
9.6/10 Exceptional! (2,049 reviews)
Beautiful river view from the patio and coffee at room. Decent breakfast in hotel and other dining options near by. Overall good experience.

Reviewed on Jun 18, 2026

The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges

2 out of 5
Historic Railroad District
Price was $1,068, price is now $874 per person
$874
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Ontario Intl. Airport (ONT) to Medford (MFR)
9.6/10 Exceptional! (107 reviews)
Beautiful rooms, walkable, comfortable rooms, really enjoyed. Great for couples

Reviewed on May 30, 2026

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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 23 to Jun 24
$132 total
Jun 23 - Jun 24
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
Super 8 by Wyndham Roseburg

Super 8 by Wyndham Roseburg

2.5 out of 5
3200 Nw Aviation Dr I-5 Exit # 127 Roseburg OR
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $93 total per night from Jun 28 to Jun 29
$93 total
Jun 28 - Jun 29
Total with taxes and fees
8/10 Very Good! (1,000 reviews)
"Quick stop to break up a road trip. It met our needs for the night, no frills great for a stop over."

Reviewed on Jun 15, 2026

Super 8 by Wyndham Roseburg
Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave Roseburg OR
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $117 total per night from Jul 6 to Jul 7
$117 total
Jul 6 - Jul 7
Total with taxes and fees
8.6/10 Excellent! (1,470 reviews)
"Very convenient and quiet property on the river."

Reviewed on Jun 17, 2026

Riverfront Inn Roseburg
See all 86 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 $391 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.