Winston Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Michelle Finseth

Top hotels in Winston

Safari Inn
Safari Inn
2 out of 5
101 NE Main Street, Winston, OR
The price is 2.357.550 ₫ per night from 25 Jul to 26 Jul
2.357.550 ₫
2.557.942 ₫ total
25 Jul - 26 Jul
includes taxes & fees
7.6/10 Good! (352 reviews)
Nice local motel value
"Very friendly. Let me check in a little early. Older property with sluggish plumbing but clean and well maintained. Felt safe. Pretty quiet besides a little road noise to be expected. Tried to book again for week later but it was full. Great place to catch up on sleep."

Reviewed on 22 Jun 2025

Safari Inn
Family-friendly Winston Vacation Rental w/ Deck!
Family-friendly Winston Vacation Rental w/ Deck!
3 out of 5
Winston
"This house was beautiful, affordable, and very spacious! It had every single amenity you would need and many extras too! The host was extremely attentive and informative with check on and out process and also making sure we could contact her at any time if needed. I definitely recommend this house ..."

Reviewed on 5 Apr 2024

Get rates
Family-friendly Winston Vacation Rental w/ Deck!
Riverfront Inn Roseburg
Riverfront Inn Roseburg
2 out of 5
315 W Harvard Ave, Roseburg, OR
Fully refundableReserve now, pay when you stay
The price is 3.394.872 ₫ per night from 25 Jun to 26 Jun
3.394.872 ₫
3.717.332 ₫ total
25 Jun - 26 Jun
includes taxes & fees
8.6/10 Excellent! (1,320 reviews)
"We especially enjoyed sitting on the balcony!"

Reviewed on 24 Jun 2025

Riverfront Inn Roseburg
See all 105 properties in Winston
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 Winston holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Winston costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Winston?
To score cheap Winston holiday packages, plan your trip outside of busy periods like public holidays and major events. You'll typically find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Winston?
The ideal length of your Winston holiday depends on what you'd like to do. Generally, a few days to a week will give you plenty of time to visit all the major sights and discover some hidden treasures along the way.
How to find the best Winston package deals?
Landing a cheap Winston package deal is easy with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply some filters and see what's available. You can tailor your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most affordable Winston package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Winston holiday as a package?
An Expedia holiday package could land you great savings when compared to booking accommodation and flights individually. Better still, you can tailor your Winston escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Winston?
Enjoy fantastic discounts by booking your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Winston escape.
How to plan a trip to Winston?

  1. Choose when to get away: Check your diary and get packing. Your favourite season and the type of activities available will also help you decide when to holiday in Winston.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and food to activities and flights. Your accommodation will probably be the biggest expense during your trip to Winston.
  3. Decide your trip length: Think about how much time you'd like to spend exploring Winston. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Winston holiday package.

Popular places to visit

Wildlife Safari

Wildlife Safari

Why not visit the animals who live at Wildlife Safari during your travels in Winston? While you're in the area, stroll along the riverfront.

Wildlife Safari

Abacela Winery

You can enjoy a tasting or tour at Abacela Winery during your travels to Winston. While you're in the area, stroll along the riverfront.

Abacela Winery