Winston Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Winston

Safari Inn

Safari Inn

2 out of 5
101 NE Main Street Winston OR
Fully refundableReserve now, pay when you stay
The price is 2.236.775 ₫ per night from 3 Aug to 4 Aug
2.236.775 ₫
2.427.032 ₫ total
3 Aug - 4 Aug
includes taxes & fees
7.6/10 Good! (381 reviews)
"Thing where held together by duct tape the room wasn’t to bad"

Reviewed on 3 Jul 2026

Safari Inn
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
The price is 2.281.247 ₫ per night from 18 Aug to 19 Aug
2.281.247 ₫
2.497.965 ₫ total
18 Aug - 19 Aug
includes taxes & fees
Super 8 by Wyndham Roseburg
SureStay by Best Western Roseburg

SureStay by Best Western Roseburg

2.5 out of 5
2855 NW Edenbower Blvd Roseburg OR
Fully refundableReserve now, pay when you stay
The price is 2.936.491 ₫ per night from 23 Aug to 24 Aug
2.936.491 ₫
3.215.458 ₫ total
23 Aug - 24 Aug
includes taxes & fees
8/10 Very good! (1,008 reviews)
"The staff are exceptional. Kind and helpful. We upgrade to a suite with a pull out couch. There was no bedding either on the bed or in the room. The bed was springy and uncomfortable. The waffle irons were dirty. Not just from use of the day. It was thickly covered with crude. The pools were great ..."

Reviewed on 23 Jul 2026

SureStay by Best Western Roseburg
See all 107 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.

Stay near popular Winston attractions

Wildlife Safari

9.2/10 (181 reviews)
Drive through 600 acres where lions, giraffes, and rhinos roam freely in natural habitats. Wildlife Safari's renowned cheetah breeding programme has produced over 230 cubs for global conservation efforts.
See properties

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.