Southern Oregon Vacations from $472

Medford offers the lowest typical prices for a week-long Southern Oregon vacation package, while Grants Pass tends to be higher. A week-long trip typically costs around $1,100 per adult in Medford, around $1,200 per adult in Ashland, and around $1,300 per adult in Grants Pass.


*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

When you bundle, you can save up to 30%*. To save money on a Southern Oregon package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

A Southern Oregon vacation package lets you combine flights, hotel stays, and rental cars, based in one of the region's top destinations like Medford, Ashland, or Grants Pass. Many hotels in Medford offer free breakfast and airport shuttle service to Medford, OR (MFR-Rogue Valley Intl.). Similarly, many hotels in Ashland also provide free breakfast and airport shuttle options. In Grants Pass, some hotels feature free breakfast and airport shuttle service.


Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

Ashland, Grants Pass, and Medford are some of the top destinations for cheap Southern Oregon vacation package deals. For an affordable weekend getaway, Ashland is often among the most budget-friendly options, with package prices starting around $410 per adult. For notable bundle savings, Ashland is also among the best options, with flight-and-hotel bundles saving around $55 per adult.


Browse cheap vacation packages in Southern Oregon on Expedia to compare current deals.


*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

The best time for a Southern Oregon vacation package depends on which destination you choose.


Medford is busiest in August and September, when highs reach around 87°F and 80°F respectively. If you'd prefer fewer crowds, January and November are quieter, with highs around 49°F and 54°F.


Ashland sees the most visitors in May, June, and July. May offers highs around 66°F, while July is warmer with highs around 86°F. The Oregon Shakespeare Festival also runs from March through October. For a quieter trip, December and March are less crowded, with highs around 45°F and 51°F.


Grants Pass is most popular in March, May, and October. May has highs around 69°F, and October sees highs around 68°F. If you prefer fewer visitors, April and November are quieter, with highs around 60°F and 55°F.

Southern Oregon, known for its outdoor activities and scenic views, offers Southern Oregon vacation packages across its top destinations with diverse travel styles:

• Budget: In Medford, The City Center Motel, rated 8.8 out of 10 by travelers, provides a value-focused stay with free breakfast and WiFi.
• Pet-friendly: For those traveling with pets, La Quinta Inn & Suites by Wyndham Grants Pass, rated 8.8 out of 10 by travelers, offers pet-friendly accommodations, an indoor pool, and a hot tub, with travelers often praising the staff for going above and beyond.
• Couples: In Ashland, Callahan's Mountain Lodge, rated 8.1 out of 10 by travelers, is a great choice for couples, featuring a bar/lounge and restaurant, and travelers frequently highlight its beautiful location.
• Family: In Medford, the 4-star Compass by Margaritaville in Medford, rated 9.1 out of 10 by travelers, suits families with its family rooms, game room, and outdoor pool, with guests often praising the wonderful pool.

For a Southern Oregon vacation, you can choose your base depending on your travel style and interests:

• Medford: A popular choice for packages, this city is a central base for romantic getaways and exploring outdoor activities, with a wide range of lodging options.
• Ashland: Ideal for cultural experiences and romantic trips, Ashland is known for its vibrant arts scene and access to outdoor adventures.
• Grants Pass: Perfect for those seeking outdoor adventure, especially river activities, while also offering a romantic setting.
• Jacksonville: This charming historic town is a good lodging base for romantic getaways and experiencing local culture, with a selection of boutique accommodations.

Southern Oregon is primarily an outdoor and nature destination, known for its scenic views and adventure activities. The region features stunning natural water bodies like Crater Lake and Upper Klamath Lake, as well as the Rogue River, perfect for water-based recreation.


Southern Oregon also boasts a rich cultural side. Ashland is home to the renowned Oregon Shakespeare Festival, while the historic town of Jacksonville hosts the popular Britt Music Festival. Medford offers theatrical performances at the Craterian Ginger Rogers Theater.


Overall, a Southern Oregon vacation package is ideal for travelers seeking outdoor adventures and natural beauty, complemented by engaging cultural experiences.

For a Southern Oregon vacation, the primary airport within the region is Medford, OR (MFR-Rogue Valley Intl.), serving the city of Medford and surrounding areas. Travelers can also consider flying into Eugene, OR (EUG), which serves the city of Eugene to the north, or Redmond, OR (RDM-Robert's Field), serving Redmond in central Oregon. The best choice depends on your specific destination within Southern Oregon.

A Southern Oregon vacation offers a diverse range of activities across its distinct towns and natural landscapes:


Browse and book things to do in Southern Oregon on Expedia.

Southern Oregon offers family vacation packages with a variety of kid-friendly amenities across its destinations:

• Homewood Suites Medford: In Medford, this hotel, rated 8.4 out of 10 by travelers, provides family rooms and an indoor pool, with travelers often noting the cleanliness of the rooms.
• Ashland Hills Hotel & Suites: In Ashland, this hotel, rated 8.2 out of 10 by travelers, features a playground and outdoor pool, and guests frequently praise the breakfast.
• La Quinta Inn & Suites by Wyndham Grants Pass: In Grants Pass, this hotel, rated 8.8 out of 10 by travelers, is a great choice for families with its indoor pool, hot tub, and kitchen facilities, and travelers highlight the well-stocked breakfast.
• Compass by Margaritaville in Medford: Also in Medford, this 4-star property, rated 9.1 out of 10 by travelers, offers a game room and an outdoor pool, with guests often praising the wonderful pool.

Booking times for a Southern Oregon vacation package vary by destination — most travelers book around 2 to 5 weeks ahead.


Travelers tend to book Southern Oregon vacation packages most often in March, and from May to October. If you're planning a spontaneous getaway, Expedia also offers last-minute Southern Oregon vacation packages.

Most Southern Oregon vacation packages last around 3 to 4 days, but the ideal trip length depends on where you're going and what you'd like to experience.


Medford, known for its outdoor activities and scenic views, is often explored with a trip of around 3 days. Most travelers opt for weekend trips, though week-long stays are also popular, allowing time to visit attractions like Lithia & Driveway Fields.


Ashland, a destination for romantic getaways and scenic views, typically calls for a trip of around 4 days. Weekend and week-long stays are both common, giving you ample opportunity to experience the renowned Oregon Shakespeare Festival.


Grants Pass, characterized by its outdoor activities and adventure, is often enjoyed with a trip of around 3 days. Most visitors choose weekend trips, with some extending to week-long stays to explore the famous Rogue River.

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Southern Oregon vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

To find last-minute vacation packages to Southern Oregon, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

Free cancellation on a Southern Oregon vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your Southern Oregon getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.