Winston Vacation Packages 2026 from $527

Winston flight + hotel vacation packages

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

Gold Beach Inn

$527

per person

Feb 19 - Feb 23

found 15 hours ago

Roundtrip non-stop flight included

Houston (IAH) 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.

Bay Point Landing

$673

per person

Feb 19 - Feb 23

found 15 hours ago

Roundtrip non-stop flight included

Houston (IAH) 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.

Edgewater Inn and Suites, an Ascend Collection Hotel

$564

per person

Feb 19 - Feb 23

found 15 hours ago

Roundtrip non-stop flight included

Houston (IAH) to North Bend (OTH)

An indoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.

Bandon Inn

$697

per person

Feb 19 - Feb 23

found 15 hours ago

Roundtrip non-stop flight included

Houston (IAH) to North Bend (OTH)

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

Jot's Resort

$533

per person

Feb 19 - Feb 23

found 15 hours ago

Roundtrip non-stop flight included

Houston (IAH) to North Bend (OTH)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area is provided and the front desk is staffed around-the-clock.

Top Winston hotels deals

Safari Inn

101 NE Main Street Winston OR

Free Cancellation

Reserve now, pay when you stay

$65 nightly

$71 total

Dec 29 - Dec 30

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

$331 nightly

$359 total

Dec 31 - Jan 1, 2026

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

Get rates

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

Kitchen

Washer

Family-friendly Winston Vacation Rental w/ Deck!

Winston OR

Get rates

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.

Kitchen

Washer

Charming cottage studio in serene environment perfect for a relaxing getaway

Winston OR

Get rates

This cottage featured laundry facilities and barbecue grills.

Washer

Dryer

Super 8 by Wyndham Roseburg

3200 Nw Aviation Dr I-5 Exit # 127 Roseburg OR

Free Cancellation

Reserve now, pay when you stay

$66 nightly

$73 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's an indoor pool on site, and a 24-hour front desk and express check-out are also provided.

Pool

Breakfast included

Don't see what you're looking for?

See all available properties in Winston

View all properties

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

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.

Frequently asked questions

How much are vacation packages to Winston?

Your travel daydreams can become a reality in Winston for only $527. 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.