Jacksonville Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Jacksonville
Wine Country Inn
830 N 5th St Jacksonville OR
Fully refundableReserve now, pay when you stay
S$143
31 Aug - 1 Sept
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Great location and hotel accommodations. Have stayed here many times and am always pleased with it."
Reviewed on 28 Aug, 2026
The Lindsay Lodge & Restaurant
15100 Oregon 238 Jacksonville OR
Fully refundableReserve now, pay when you stay
S$285
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (49 reviews)
"Weak breakfast"
Reviewed on 16 Aug, 2026
Magnolia Hotel
245 North 5th Street Jacksonville OR
Fully refundableReserve now, pay when you stay
S$223
31 Aug - 1 Sept
includes taxes & fees
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 Jacksonville attractions
Applegate Lake
9.2/10 (13 reviews)
Surrounded by the Rogue River-Siskiyou National Forest, Applegate Lake offers pristine waters for trout and bass fishing. Explore scenic hiking trails that wind through forested mountains for spectacular lake views.
Photo by Ann Sair
Red Lily Vineyards
9.8/10 (11 reviews)
Red Lily Vineyards specialises in Spanish-inspired Tempranillo wines with tastings in a scenic riverside setting. Enjoy vintages on the outdoor patio or bring a picnic to savour among the expansive grounds.
Britt Pavilion
9.6/10 (43 reviews)
This hillside amphitheatre hosts the renowned Britt Music & Arts Festival amid towering ponderosa pines. Bring a blanket for lawn seating and enjoy world-class performances under starlit Oregon skies.
Buncom
This preserved ghost town showcases Oregon's gold mining era with three historic buildings. Wander through the 1910 post office and experience the quiet rural atmosphere of this once-bustling community.
Valley View Winery
9.0/10 (8 reviews)
One of Oregon's oldest wineries, Valley View offers award-winning handcrafted wines in a converted hay barn setting. Savour tastings on the pavilion overlooking Applegate Valley's picturesque landscape.
Art Presence Art Center
Enjoy a performance at Art Presence Art Center, a popular theatre in Jacksonville. While you're here, you can savour the top-notch restaurants.
Applegate Library
Applegate Library: a vibrant community hub with diverse resources for literacy and lifelong learning. Browse their thoughtfully curated collection or join seasonal programmes like the "Rogue Reads" series.
Beekman House
10.0/10 (1 review)
Step into C.C. Beekman's Gothic Revival home, filled with authentic family artefacts from Victorian times to post-WWII. Experience pioneer wealth through guided tours that illuminate Jacksonville's gold rush history.
What to do in Jacksonville
The Cultural Heart of Ashland: A Self-Guided Audio Tour
S$13
per adult
Frequently asked questions
How much does a Jacksonville holiday package cost?
You'll find cheap prices 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 holiday to Jacksonville costs.
What are the cheapest months to go to Jacksonville?
If you're looking to snag a cheap Jacksonville holiday package, consider visiting in January, February and March. You'll generally find lower prices on airfares and hotels during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Jacksonville?
For your Jacksonville holiday, a few days will be enough to tour the highlights. Make sure to check out Beekman House — it's one of the major sights in this destination. If you want more activities, consider basing yourself here and heading off on some day trips from Jacksonville.
Is it worth booking a holiday package to Jacksonville?
Jacksonville has everything you need for an awesome getaway — history, nature and hiking are just the start. Whether you want to visit sights such as Britt Pavilion and Beekman House, or take the path less traveled, you'll have plenty to experience on your Jacksonville holiday.
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 holiday as a package?
You can enjoy significant savings on your Jacksonville retreat by booking a customised holiday 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 holiday 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?
- Pick the right time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Jacksonville.
- Set a budget: Factor in expenses like flights, food and transportation when calculating how much to save for your trip to Jacksonville. Then, pick a hotel that fits your budget, whether that's an economical option or a more luxurious getaway.
- Work out your trip length: Consider how much time you want to spend exploring Jacksonville. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Jacksonville holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
