Winston Vacation Packages 2026 from $648

Winston flight + hotel vacation packages

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

Wild Rivers Motor Lodge

$648

per person

Nov 6 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to North Bend (OTH)

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A safe deposit box is also provided.

Siltcoos Station Retreats

$1,104

per person

Nov 15 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to North Bend (OTH)

This aparthotel features a garden, barbecue grills, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A picnic area and a virtual front desk are also provided.

The Florentine Waterfront Hotel

$1,174

per person

Nov 15 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to North Bend (OTH)

This hotel features a lazy river and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.

Bay Point Landing

$1,093

per person

Nov 15 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to North Bend (OTH)

A private beach and an indoor pool are featured at this aparthotel. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A business center, a grocery/convenience store, and a picnic area are also on offer.

Gold Beach Inn

$859

per person

Nov 15 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to North Bend (OTH)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.

Top Winston hotels deals

Safari Inn

101 NE Main Street Winston OR

$70 nightly

$76 total

Oct 26 - Oct 27

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Parking included

Free WiFi

The Watusi Place - A Modern Umpqua Valley Getaway

Winston OR

$357 nightly

$387 total

Oct 7 - Oct 8

Total with taxes and fees

This vacation home featured laundry facilities and barbecue grills.

Kitchen

Washer

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

Winston OR

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This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

Family-Friendly Winston Vacation Rental w/ Deck!

Winston OR

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A gym is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

Kitchen

Washer

Riverfront Inn Roseburg

315 W Harvard Ave Roseburg OR

$80 nightly

$87 total

Oct 7 - Oct 8

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's an outdoor pool on site, and a 24-hour front desk and a terrace are also provided.

Pool

Breakfast included

SureStay by Best Western Roseburg

2855 NW Edenbower Blvd Roseburg OR

$98 nightly

$107 total

Oct 12 - Oct 13

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

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.

Stay near popular Winston attractions

Wildlife Safari

9.2/10 (181 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.

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Frequently asked questions

How much are vacation packages to Winston?

Your travel daydreams can become a reality in Winston for only $648. 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 60 mi southeast of Winston, it welcomes visitors from all over every day. Another good option is Southwest Oregon Regional Airport (OTH), 45 mi 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.