Winston Vacations 2026 from CA $819

Winston flight + hotel packages

Price found within the past 48 hours. Click for updated prices.

Anchor Bay Inn

CA $819

per person

May 6 - May 10

just found

Roundtrip non-stop flight included

Edmonton (YEG) to North Bend (OTH)

Book a stay at this business-friendly motel in Reedsport. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Umpqua Discovery Center and Umpqua River are located nearby.

Bay Point Landing

CA $1,043

per person

May 6 - May 10

just found

Roundtrip non-stop flight included

Edmonton (YEG) to North Bend (OTH)

Stay at this aparthotel in Coos Bay. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Coos Historical & Maritime Museum and Mingus Park are located nearby.

Red Lion Hotel Coos Bay

CA $1,020

per person

May 6 - May 10

just found

Roundtrip non-stop flight included

Edmonton (YEG) to North Bend (OTH)

Book a stay at this business-friendly hotel in Coos Bay. Enjoy free WiFi, free parking, and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Mingus Park and Coos Art Museum are located nearby.

Bandon Inn

CA $1,194

per person

May 6 - May 10

just found

Roundtrip non-stop flight included

Edmonton (YEG) to North Bend (OTH)

Stay at this motel in Bandon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bandon Dunes Golf Resort and Pacific Blues are located nearby.

Jot's Resort

CA $841

per person

May 6 - May 10

just found

Roundtrip non-stop flight included

Edmonton (YEG) to North Bend (OTH)

Stay at this hotel in Gold Beach. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Patterson Bridge and Collier Buffington Memorial Park are located nearby.

Top Winston hotels deals

Safari Inn

101 NE Main Street Winston OR

CA $82

CA $89 total

Mar 2 - Mar 3

includes taxes & fees

Stay at this motel in Winston. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions South Umpqua River and Wildlife Safari are located nearby.

Parking included

Free WiFi

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Winston OR

Get rates

Stay at this vacation home in Winston. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions South Umpqua River and Wildlife Safari are located nearby.

Kitchen

Washer

The Watusi Place - A Modern Umpqua Valley Getaway

Winston OR

CA $203

CA $499 total

Mar 1 - Mar 2

includes taxes & fees

Stay at this vacation home in Winston. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Abacela Winery and Wildlife Safari are located nearby.

Kitchen

Washer

Charming cottage studio in serene environment perfect for a relaxing getaway

Winston OR

CA $219

CA $251 total

Mar 1 - Mar 2

includes taxes & fees

Washer

Dryer

Holiday Inn Express Roseburg by IHG

375 Harvard Blvd Roseburg OR

Free cancellation

Reserve now, pay when you stay

CA $135

CA $148 total

Mar 8 - Mar 9

includes taxes & fees

Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Stewart Park and Umpqua Valley Tennis Center are located nearby.

Pool

Breakfast included

SureStay by Best Western Roseburg

2855 NW Edenbower Blvd Roseburg OR

Free cancellation

Reserve now, pay when you stay

CA $98

CA $108 total

Mar 1 - Mar 2

includes taxes & fees

Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Umpqua Valley Tennis Center and Stewart Park are located nearby.

Pool

Breakfast included

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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.

Popular places to visit

Wildlife Safari

5/5(2 reviews)

Why not see the exotic and native animals who live at Wildlife Safari during your vacation in Winston? While you're in the area, stroll along the riverfront.

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.

Winston Vacations

If you were sick the day your geography teacher taught your class where Winston is situated, don't worry. With a little help from us, you'll find it in a flash!

You'll discover this Roseburg neighborhood 15 miles (24 kilometers) southwest of the downtown area.

There are 21,000 locals that call Roseburg home.

Places to visit in Winston

Snowboarding is a popular activity in Roseburg and a superb excuse to get out and discover more of this unique region. If you're really looking to create some unforgettable vacation memories, put skiing on your itinerary too.

Where do you fly into for Winston?

If you're traveling to Winston, the closest terminal is Southwest Oregon Regional Airport (OTH). It's around 45 miles (72 kilometers) northwest from the central area. Select an in-flight movie, sit back and relax and you'll arrive in no time at all.

Frequently asked questions

How much are vacation packages to Winston?

Your travel daydreams can become a reality in Winston for only CA $819. Package deals include flights and hotels, so organizing your itinerary will be easy as pie. All you'll have to concentrate on is getting out there and having a great time.

How long should my Winston vacation be?

Around 2 nights is the average time frame travelers vacation in Winston. But how long is right for you depends on how many cherished memories you want to create. Why not stay a couple of extra days and uncover some hidden treasures?

Where can I get the best vacation package deals for Winston?

You can score sensational Winston package deals with Travelocity. Mix and match from as many as 400 partner airlines and 1,000,000 properties worldwide and turn your travel dreams into a reality.

Why should I book my Winston vacation package with Travelocity?

Nothing beats the peace of mind knowing you've scored the best deal in town — that's our Price Match Guarantee. Add to that our enormous range of magical destinations and 24/7 team of customer service professionals and you've got the formula for a hassle-free vacation.

Will I save money on my Winston car rental if I combine it with my hotel or flight?

Definitely. And our Winston vacation packages are the best way to do it. In just a few clicks you can save cash as well as time by booking everything in one place. Pick up the keys to your rental car and do your vacation your way. Need to fill your itinerary? Add some activities or experiences to your package and make savings on those too.

Which airport is best for Winston?

Rogue Valley Intl. Airport (MFR) is the gateway to your Winston adventure. Located 97 kilometers southeast of Winston, it welcomes visitors from all over every day. Another good option is Southwest Oregon Regional Airport (OTH), 72 kilometers away from central Winston.

What is there to do in Winston?

You'll find some excellent photo opportunities at Abacela Winery, one of the most visited attractions in Winston. There's a whole lot more to discover in this great destination, so make sure you have enough time to explore some hidden gems.

Where should I stay when visiting Winston?

Many visitors choose to spend their nights at the Wildlife Inn. It's the perfect base for your Winston getaway.