Jacksonville Holidays

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Top hotels in Jacksonville

Wine Country Inn

Wine Country Inn

3 out of 5
830 N 5th St Jacksonville OR
Fully refundableReserve now, pay when you stay
The price is S$149 per night from 9 Aug to 10 Aug
S$149
9 Aug - 10 Aug
includes taxes & fees
9.4/10 Exceptional! (1,008 reviews)
"Very clean"

Reviewed on 10 Jul, 2026

Wine Country Inn
The Lindsay Lodge & Restaurant

The Lindsay Lodge & Restaurant

2 out of 5
15100 Oregon 238 Jacksonville OR
Fully refundableReserve now, pay when you stay
The price is S$266 per night from 21 Jul to 22 Jul
S$266
21 Jul - 22 Jul
includes taxes & fees
9/10 Wonderful! (43 reviews)
"We loved everything about the place and the wonderful service."

Reviewed on 2 Jul, 2026

The Lindsay Lodge & Restaurant
Magnolia Hotel

Magnolia Hotel

3 out of 5
245 North 5th Street Jacksonville OR
The price is S$261 per night from 20 Jul to 21 Jul
S$261
20 Jul - 21 Jul
includes taxes & fees
9/10 Wonderful! (786 reviews)
"Wonderful, all too brief stay.High attention to design details; Would definitely stay here again."

Reviewed on 1 Jul, 2026

Magnolia Hotel
See all 951 properties in Jacksonville
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

A serene lake surrounded by dense forests and snow-capped mountains under a colorful sky.

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.
See properties

What to do in Jacksonville

Floating towards the sunset on the Rogue River

Rogue River Golden Hour Evening Float Trip

S$154
per adult
Rogue River Golden Hour Evening Float Trip
An Audio Tour Through the Heart of Ashland, Oregon

The Cultural Heart of Ashland: A Self-Guided Audio Tour

S$13
per adult
The Cultural Heart of Ashland: A Self-Guided Audio Tour
See all activities in Jacksonville

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.

Explore a world of travel with Expedia

* 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.