Winston Holidays

Photo by Michelle Finseth
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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

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 S$96 per night from 24 Jun to 25 Jun
S$96
24 Jun - 25 Jun
includes taxes & fees
7.6/10 Good! (349 reviews)
"Everything"

Reviewed on 22 Apr, 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 S$166 per night from 19 Jun to 20 Jun
S$166
19 Jun - 20 Jun
includes taxes & fees
8.4/10 Very Good! (1,302 reviews)
"The staff makes an extra effort to make sure that everything is superior."

Reviewed on 14 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.

What to do in Winston

4 Day Ngorongoro Crater Tarangire and Serengeti National Park

4 Day Ngorongoro Crater Tarangire and Serengeti National Park

S$1,156
per adult
4 Day Ngorongoro Crater Tarangire and Serengeti National Park
See all activities in Winston

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.