Riddle Vacations from ￥66,126
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- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
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The Latest Riddle Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Peerless Hotel by WanderLodges
Historic Railroad District
￥77,049
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Medford (MFR)
9.6/10 Exceptional! (110 reviews)
The place was cute. Room was really nice and bed was comfy. Close to downtown. Would stay there again.
Reviewed on Aug 13, 2026
Hummingbird Estate Wine & Suites
￥74,493
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Medford (MFR)
9.6/10 Exceptional! (176 reviews)
Beautiful grounds and adorable, clean room. The bed was very comfortable. We'll stay here again next time!
Reviewed on Aug 11, 2026
A Cowslip's Belle Inn
￥90,680
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Medford (MFR)
9.6/10 Exceptional! (48 reviews)
The Cowslips Belle Inn is amazing! Just a few short blocks from the Oregon Shakespeare Festival, many fine eateries and downtown Ashland. The grounds are superb with well tended landscaping, cozy seating areas and a wonderful koi pond. An off street parking area just for guests is excellent. The hosts were very gracious and friendly, personally greeting us and showing us our suite. The suite is beautifully decorated and very cozy with all the amenities that one might need. The notebook with restaurant recommendations, outlines of all the possibilities of things to do and entertainments in the area plus bios on all 3 hosts is a real plus. And the price is excellent for this wonder! Would highly recommend this Inn for a short or long stay in Southern Oregon.
Reviewed on Aug 7, 2026
Find the Best Riddle Vacation Packages
Riddle Hotel Deals
Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
Riddle OR
￥11,949
￥21,022 total
Sep 16 - Sep 17
includes taxes & fees
9.8/10 Exceptional! (99 reviews)
"This room in the country was exactly what I needed while attending a wedding in the area.Host Kathie was very personable, met me at check in to show me around. She went above and beyond to ensure everything was just right.I will definitely be booking this sweet place in the future if the need ..."
Reviewed on Jul 29, 2026
Super 8 by Wyndham Roseburg
3200 Nw Aviation Dr I-5 Exit # 127 Roseburg OR
Fully refundableReserve now, pay when you stay
￥11,925
￥13,058 total
Sep 15 - Sep 16
includes taxes & fees
7.8/10 Good! (1,005 reviews)
"Very odd experience. when I checked in, the girl was on her phone, talking to someone. She kept talking to them while collecting my information. After 5 minutes of "double tasking" she hung up the phone then proceeded to advertise and sell me one of her "paintings". I told her I was tired and needed ..."
Reviewed on Aug 17, 2026
Riverfront Inn Roseburg
315 W Harvard Ave Roseburg OR
Fully refundableReserve now, pay when you stay
￥15,456
￥16,924 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (1,496 reviews)
"It was our second time to stay there. The first time, a year ago it seemed much nicer. The people that are employed there are very friendly and helpful, but the facility itself is old and worn out. Clean, but worn out! I would still stay there again, because it is cost-efficient for what you ..."
Reviewed on Aug 18, 2026
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.
Frequently asked questions
How much does a Riddle vacation package cost?
Offering excellent value package deals from ￥66,126 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?
Plan your trip for the low or shoulder season and you're likely to get cheap Riddle vacation packages. Remember that public holidays and local festivals and events can impact prices, so do some research before you go.
How many days is enough for Riddle?
Typically, a handful of days is enough to check out the top sights during your Riddle vacation. However, if you want to have more time to rest or go on day trips, think about extending your trip.
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.
How to plan a trip to Riddle?
- Choose the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to travel to Riddle.
- Figure out your budget: Make sure you have enough money to cover everything from food and transportation to activities and flights. Your hotel will probably be the largest expense during your trip to Riddle.
- Decide how long to go for: Now that you're more familiar with Riddle, you can figure out the right length of your break. Put together a rough plan and allocate enough time to get through everything on your must-do list.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Riddle vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
