Jacksonville Vacations from $290

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Your Jacksonville Vacation

From its diversity to its sunny weather and beyond, there's a whole lot to love about Jacksonville. Discover the wonders of this captivating city with a Jacksonville vacation package that's made for you. Every trip to Jacksonville needs a well-crafted itinerary. Fill yours with big-name attractions like Britt Pavilion, Jacksonville Cemetery and Art Presence Art Center. Your Jacksonville vacation is just clicks away. Explore flights, hotels and more on Expedia for a trip that's tailored just for you.

The Latest Jacksonville vacation packages

Price found within the past 48 hours. Click for updated prices.
Clarion Pointe Medford
Hummingbird Estate Wine & Suites
Compass by Margaritaville in Medford
Wine Country Inn
Paschal Winery
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Discover the most popular places to visit in Jacksonville

What to do in Jacksonville

Jacksonville Hotel Deals

Wine Country Inn

Wine Country Inn

3 out of 5
830 N 5th St Jacksonville OR
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $117 total per night from Jan 21 to Jan 22
$117 total
Jan 21 - Jan 22
Total with taxes and fees
9.4/10 Exceptional! (1,000 reviews)
Staff were friendly, room was cleaning and very nice. The end is also very dog friendly! They give you a blanket for the dog and a dish! Oh, And dog treats and dog bags to pick up the poop! Very, very nice place

Reviewed on Jan 1, 2026

Wine Country Inn
The Orth House Inn by Remotion

The Orth House Inn by Remotion

3.5 out of 5
105 W Main St Jacksonville OR
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $209 total per night from Feb 18 to Feb 19
$209 total
Feb 18 - Feb 19
Total with taxes and fees
9.2/10 Wonderful! (22 reviews)
My husband and I spent the weekend at the Orth house. We had tickets to a night at the Brit and wanted to stay within walking distance. We loved this hideaway with its old world charm, lovely wine and even a ghost story. We were also able to walk all over town and didn’t need to drive for 2 days. ...

Reviewed on Sep 8, 2025

The Orth House Inn by Remotion
Charleen's Cottage~Couple Perfect!Great Location! A Gem!

Charleen's Cottage~Couple Perfect!Great Location! A Gem!

Jacksonville OR
$101 nightly
The price is $112 total per night from Jan 21 to Jan 22
$112 total
Jan 21 - Jan 22
Total with taxes and fees
9.8/10 Exceptional! (192 reviews)
Nice place!

Reviewed on Dec 29, 2025

Charleen's Cottage~Couple Perfect!Great Location! A Gem!
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.

Find the Best Jacksonville Vacation Packages

Things to do in and around Jacksonville

Jacksonville, Oregon offers a charming blend of outdoor activities and romantic scenery, making it a perfect vacation spot. Explore the beautiful Jacksonville Arboretum, enjoy local theater performances, and attend lively music concerts. For those seeking nightlife experiences, there are various venues to discover. Additionally, consider taking a day trip to enjoy the surrounding natural beauty and partake in numerous outdoorsy activities that the area has to offer.

Shopping

In Jacksonville, explore charming local shops like Kharmic Creations and Rogue Creamery, both showcasing unique gifts. If you're up for a drive, check out Rogue Valley Mall, just 5 miles away, where you can enjoy a variety of stores and entertainment options for a fun shopping experience.

Recreation

Experience live music at Britt Pavilion, where the vibrant atmosphere enhances your enjoyment. For tranquility, head to Fichtner-Mainwaring Park, where you can unwind in nature. Craterian Ginger Rogers Theatre offers cultural performances, perfect for a romantic or family outing while soaking in the local arts scene.

Adventure

The Beekman Loop Trail offers a scenic hiking experience with beautiful landscapes and a sense of adventure, perfect for outdoor enthusiasts. The Sarah Zigler Interpretive Trail invites you to explore nature through engaging educational signs along the way, while the Enchanted Forest Trail provides a magical hiking experience amidst lush greenery.

Nightlife

Jacksonville offers a charming nightlife with cozy venues like the historic Bella Union Restaurant & Saloon, perfect for dinner and drinks. For live music, check out the intimate setting at the Jacksonville Inn. Enjoy a laid-back evening under the stars in this picturesque town.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Jacksonville

Jacksonville, Oregon, is perfect for outdoor enthusiasts and those seeking a romantic getaway, offering beautiful scenery and a rich cultural experience. Visit local attractions like the library, historic civic buildings, and nearby lakes. Families and city explorers will enjoy the Jacksonville Zoo, Jacksonville Museum, and Jacksonville Beach, while those intrigued by the supernatural can explore Jacksonville's ghost tours. This charming town has something for everyone looking to create lasting memories.

  • Applegate Lake: Nestled within Jacksonville, Applegate Lake offers a serene escape with its beautiful beaches and stunning scenery. Perfect for outdoor enthusiasts, this spot is ideal for swimming, picnicking, or simply soaking in the romantic vibes while enjoying the tranquil surroundings.
  • Buncom: Experience the quaint charm of Buncom, a historic neighborhood within Jacksonville. Known for its cozy city vibes, this small town is a perfect place to explore local history and enjoy a leisurely stroll through its picturesque streets.
  • Medford City Hall: Located 5 miles from Jacksonville, Medford City Hall is a historic civic building that showcases the rich culture of the area. Take a moment to appreciate its architectural beauty and immerse yourself in the local heritage.

Best time to go to Jacksonville

The best time to visit Jacksonville is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is sunny with no rain. December is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January36.9°F (2.7°C)Light RainMostly SunnyAverageSlightly Low
February37.2°F (2.9°C)Light RainMostly SunnyAverageSlightly Low
March39.7°F (4.3°C)Light RainMostly CloudyAverageAverage
April45.1°F (7.3°C)Light RainMostly SunnySlightly HighAverage
May52.3°F (11.3°C)Light RainMostly SunnyAverageAverage
June59.5°F (15.3°C)No RainMostly SunnySlightly HighSlightly High
July68.5°F (20.3°C)No RainSunnySlightly HighSlightly High
August68.4°F (20.2°C)No RainSunnyAverageSlightly High
September61.5°F (16.4°C)No RainSunnyAverageAverage
October51.4°F (10.8°C)Light RainMostly SunnySlightly LowAverage
November41.4°F (5.2°C)Light RainMostly SunnySlightly LowAverage
December35.4°F (1.9°C)Light RainMostly CloudySlightly LowSlightly Low

Tips to save on your trip to Jacksonville

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Jacksonville.
  • Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Jacksonville.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Jacksonville Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rogue Valley Intl. Airport (MFR)
Population
2,900
Max Temp Winter
45ºF
Max Temp Summer
80ºF
Top Sights
Red Lily Vineyards, Cricket Hill Winery and Devitt Winery and Vineyards

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Frequently asked questions

How much does a Jacksonville vacation package cost?
You'll find cheap prices from $290 on Expedia for your Jacksonville break. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Jacksonville costs.
What are the cheapest months to go to Jacksonville?
January, August and December are great times to look for cheap Jacksonville vacation packages. Opting to travel in quieter months means you can usually find better prices on flights and accommodations.
How many days is enough for Jacksonville?
You can easily explore all the main attractions in Jacksonville within a few days, including the must-see Beekman House. If you're looking for an extended Jacksonville vacation, look at what kind of day tours and activities are available in the area.
Is it worth booking a vacation package to Jacksonville?
Popular for its nature, hiking and history, a Jacksonville vacation has something for everyone. Be sure to visit top sights like Britt Pavilion and Beekman House, and consider renting a set of wheels for day trips to explore even more.
How to find the best Jacksonville package deals?
Begin your search for a Jacksonville package deal by entering your destination and travel dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Jacksonville package deal right away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Jacksonville adventure underway.
Is it cheaper to book a Jacksonville vacation as a package?
You can enjoy significant savings on your Jacksonville retreat by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Jacksonville?
Score amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Jacksonville adventure.
How to plan a trip to Jacksonville?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Jacksonville.
  2. Work out your budget: Make sure you have enough money to pay for everything from meals and transportation to activities and flights. Your accommodations will likely be the biggest expense during your trip to Jacksonville.
  3. Discover Jacksonville with Expedia's trip planning tool: Gain insights into the top attractions and best properties for your trip to Jacksonville. You can also save your must-visit places, collaborate with family and friends and arrange all your plans in one place.
  4. Determine how many days away: Start by compiling a list of the attractions you want to experience in Jacksonville. Then, estimate how long you'll need for each, including any travel time.
  5. Bundle your airfare and accommodations: After you've settled on your dates and duration, book the right Jacksonville vacation package for you.
  6. Add on excursions and experiences: Read our dedicated travel guide to find some fun things to do in Jacksonville. Book tickets or make reservations as soon as you can to save time and skip the hassle of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later Jacksonville vacation packages?
If you're anything like us, you love traveling but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Jacksonville vacation across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.