Winston Holidays

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    Packages with flights are ATOL protected

Your Winston Holiday

From its rural countryside to its friendly locals and beyond, there's plenty to like about Winston. Uncover the wonders of this awesome city with a Winston holiday package that's made for you. Wildlife Safari, South Umpqua River and Douglas County Museum of History and Natural History are just some of the attractions you'll want to explore during your trip to Winston. Expedia will help you escape the everyday. Tailor your holiday to Winston to match your travel style, whatever that may be.

Winston Essential Information

Language
English
Currency
U.S dollars
Population
5,400
Max Temp Winter
10ºC
Max Temp Summer
27ºC
Top Sights
Wildlife Safari, Melrose Vineyards and HillCrest Winery and Distillery

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 £72 per night from 18 Jul to 19 Jul
£72
18 Jul - 19 Jul
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
The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway

Winston OR
The price is £296 per night from 28 Jul to 29 Jul
£296
28 Jul - 29 Jul
includes taxes & fees
10/10 Exceptional! (54 reviews)
"Clean, fully updated, great location! The Wildlife Safari was a lot of fun, just 2min away. Easy drive to Crater Lake, a must-see. Great property!"

Reviewed on 28 Jun 2026

The Watusi Place - A Modern Umpqua Valley Getaway
Family-Friendly Winston Vacation Rental w/ Deck!

Family-Friendly Winston Vacation Rental w/ Deck!

Winston OR
10/10 Exceptional! (19 reviews)
"The house was very nice for our purposes. My 4 year old son found the kids room and all the books and games to be an awesome treat. The house was very well appointed, we had everything we needed to cook, clean and have fun. If you're looking to be close to the wildlife safari, it's less than 10 minutes ..."

Reviewed on 12 Sept 2025

Get rates
Family-Friendly Winston Vacation Rental w/ Deck!
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.
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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

What to do in Winston

4 Day Ngorongoro Crater Tarangire and Serengeti National Park

4 Day Ngorongoro Crater Tarangire and Serengeti National Park

£669
per adult
4 Day Ngorongoro Crater Tarangire and Serengeti National Park
See all activities in Winston

Frequently asked questions

How much does a Winston travel package cost?
Chart your own course with our Winston travel packages, which start from just . Choose the flights and hotels that suit your travel plans. Then, add on a few tours or activities for an amazing adventure.
If I'm not able to travel, can I cancel my Winston travel package?
Yes you can, and we'll help you every step of the way. You may be able to cancel or change your Winston travel package for free within 24 hours of booking. But you may be charged a fee by your hotel, airline or car rental company if you booked more than 24 hours ago. If your travel plans suddenly change, have a look at our Customer Service Portal for further information.
How do I get a cheap travel package to Winston?
Crafting your own Winston travel package with Expedia is a great way to save. We have more than 550 airlines and 1,000,000 hotels all over the world. With such an amazing range to choose from, you'll have no issues creating your next dream adventure.
Does Expedia offer Book Now, Pay Later Winston holidays?
Expedia has joined forces with online lender Klarna to make booking your next getaway easier on your wallet. Paying in instalments means you can spread the costs of your next dream escape, leaving you with more money to play with while you're away. Klarna has several payment plans to pick from, so you're sure to find one that fits your budget. Check out these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month sounds best for you, Klarna offers just that! Paying in easy monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: If you'd like to pay for your getaway in multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Hitting the "book now" button is much easier with this payment option. Simply put down a small deposit on your holiday and then start working on your travel itinerary.

Where should I stay in Winston?
Stay where the action is. Many visitors favor hotels around popular attractions, such as Wildlife Safari, Spangler Vineyards and Abacela Winery.
What are the top hotels in Winston?
Best Western Plus Hood River Inn and DoubleTree by Hilton Hotel Portland are a couple of the most sought-after hotels in Winston. Why not check out the rates and facilities at each and then decide?
How far in advance should I book my Winston holiday?
It's difficult to pick the ideal time for airfares, but we generally say the earlier, the better. Many international journeys on Expedia become available to compare up to a year in advance. If you're booking last minute, don't worry. Low prices occasionally appear just weeks before departure dates.
What does an Expedia Winston travel package include?
With Expedia, you can select any combination of flights, hotels and car rentals to create your ideal Winston travel package. Once you've made your booking, you can add on the fun things like tours and activities. Remember — the more you bundle, the more you stand to save!
What should I know before booking a Winston travel package?
You can save big by combining your hotels, flights and rental cars. Once you've created your package, you can add on activities or tours. Your next awesome adventure is only a few clicks away.
Can I choose my airline with a Winston Expedia travel package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines throughout the world. Our travel packages give you the freedom to pick from available flight, hotel or activity options that suit you.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.