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$204 per night from 20 Aug to 21 Aug
S$204
20 Aug - 21 Aug
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Convenient breakfast Great bed (and I am a picky sleeper) Areas to walk the service dog. Wonderful welcome bag for the dog. Shady areas for relaxing on a hot day (it was 103) Close to everything"

Reviewed on 13 Aug, 2025

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$314 per night from 18 Aug to 19 Aug
S$314
18 Aug - 19 Aug
includes taxes & fees
8.4/10 Very Good! (26 reviews)
"We celebrated our 39th anniversary had a very special Celebration and the restaurant food was delicious. We never left the property we ate all our meals there and I highly recommend Lindsay Lodge"

Reviewed on 12 Aug, 2025

The Lindsay Lodge & Restaurant
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
The price is S$293 per night from 14 Sept to 15 Sept
S$293
14 Sept - 15 Sept
includes taxes & fees
9.2/10 Wonderful! (15 reviews)
"It was a lovely stay!"

Reviewed on 30 Jul, 2025

The Orth House Inn by Remotion
See all 899 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.

What to do in Jacksonville

Salem Puzzling Adventure

Ashland Puzzling Adventure

S$45
per traveller
Ashland Puzzling Adventure
Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

S$54
per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
Rafting Kikacéki

Kikacéki (Ward's) Canyon

S$320
per adult
Kikacéki (Ward's) Canyon
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.

* 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.