Jacksonville Vacations from $259

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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.
Super 8 by Wyndham Central Pt Medford

Super 8 by Wyndham Central Pt Medford

2 out of 5
Price was $338, price is now $259 per person
$259
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Medford (MFR)
7.2/10 Good! (1,012 reviews)
Loved the hot tub and pool.

Reviewed on Oct 1, 2025

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Price was $692, price is now $546 per person
$546
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Medford (MFR)
9.2/10 Wonderful! (571 reviews)
Very welcoming and hospitable staff. The breakfasts are delish, especially the fritata. Their attention to details are very strong.

Reviewed on Aug 15, 2025

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
Historic Downtown District
Price was $581, price is now $464 per person
$464
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Medford (MFR)
9.2/10 Wonderful! (1,001 reviews)
The hotel was peaceful and the room I was in was very nice and clean. The view from my window was spectacular. Dining options around the area were nice. I was really happy for the parking garage offered to hotel guests as well. I came to watch a Shakespeare play and it was extremely walkable to the theater.

Reviewed on Sep 29, 2025

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
Price was $487, price is now $392 per person
$392
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Medford (MFR)
9.6/10 Exceptional! (991 reviews)
Staff was very nice and very helpful. Property was very clean and nice.

Reviewed on Sep 29, 2025

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
Price was $583, price is now $478 per person
$478
per person
Nov 14 - Nov 18
found 20 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Medford (MFR)
9/10 Wonderful! (1,466 reviews)
Great clean spacious rooms with a cool retro vibe

Reviewed on Sep 30, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Jacksonville

One of about a dozen wineries located here along the Applegate Wine Trail.

Red Lily Vineyards

You can enjoy a tasting or tour at Red Lily Vineyards during your travels to Jacksonville. Discover the coffeehouses and festivals in this relaxing area.

Red Lily Vineyards

Britt Pavilion

Get tickets for a show at Britt Pavilion, a storied theater in Jacksonville. While you're here, you can savor the top-notch restaurants.

Britt Pavilion

Applegate Lake

Commune with nature and explore the great outdoors at Applegate Lake during your travels in Jacksonville. Discover the restaurants and live music in this walkable area.

Applegate Lake

What to do in Jacksonville

Salem Puzzling Adventure

Ashland Puzzling Adventure

$35
per traveler
Ashland Puzzling Adventure
4 Day Wilderness Raft Trip on the Rogue River

4 Day Wilderness Raft Trip on the Rogue River

$1,550
per adult
4 Day Wilderness Raft Trip on the Rogue River
See all activities 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
$112 nightly
The price is $123 total per night from Oct 12 to Oct 13
$123 total
Oct 12 - Oct 13
Total with taxes and fees
9.2/10 Wonderful! (1,011 reviews)
"Very charming inn in a very charming historical town."

Reviewed on Sep 25, 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
$232 nightly
The price is $236 total per night from Nov 1 to Nov 2
$236 total
Nov 1 - Nov 2
Total with taxes and fees
8.6/10 Excellent! (30 reviews)
"The staff at the lodge and restaurant were absolutely amazing. They all acted like family and loved what they do and wanted to make sure we were enjoying ourseourselves...i"

Reviewed on Sep 16, 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
$204 nightly
The price is $220 total per night from Nov 1 to Nov 2
$220 total
Nov 1 - Nov 2
Total with taxes and fees
9.2/10 Wonderful! (20 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
See all 907 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.

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Frequently asked questions

How much does a Jacksonville vacation package cost?
You'll find cheap prices from $259 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.

Explore a world of travel with Expedia

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.