Book Holiday Homes in Jacksonville

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Featured Holiday Homes in Jacksonville

Jacksonville Place

Jacksonville Place

Medford OR
A stay at this vacation home places you in the heart of Medford, within a 5-minute drive of Blackbird Statue and Stewart Meadows Golf Course.
Opens in a new windowJacksonville Place
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

Ashland OR
The price is AU$855 per night from 28 Jan to 29 Jan
AU$855
28 Jan - 29 Jan 2026
includes taxes & fees
Located in Ashland, this vacation home is within a 15-minute walk of Ashland Creek and Lithia Park.
Opens in a new windowHistoric Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
New house with king beds and 3 full bathrooms

New house with king beds and 3 full bathrooms

Medford OR
The price is AU$420 per night from 5 Jan to 6 Jan
AU$420
5 Jan - 6 Jan 2026
includes taxes & fees
A stay at this vacation home places you in the heart of Medford, within a 5-minute drive of Medford Railroad Park and Rogue Karting.
Opens in a new windowNew house with king beds and 3 full bathrooms
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New Downtown 3 Bedroom Upstairs Flat with views

New Downtown 3 Bedroom Upstairs Flat with views

Ashland OR
A stay at this vacation home places you in the heart of Ashland, steps from Ashland Library and 6 minutes by foot from Oregon Cabaret Theatre.
Opens in a new windowNew Downtown 3 Bedroom Upstairs Flat with views
East Main Downtown Bungalow

East Main Downtown Bungalow

Ashland OR
The price is AU$320 per night from 31 Dec to 1 Jan
AU$320
31 Dec - 1 Jan 2026
includes taxes & fees
With a stay at this vacation home in Ashland (Historic Railroad District), you'll be steps from Ashland Library and 6 minutes by foot from Oregon Cabaret ...
Opens in a new windowEast Main Downtown Bungalow
The River House with Views of the Famous Rogue River! No cleaning fees!

The River House with Views of the Famous Rogue River! No cleaning fees!

Grants Pass OR
The price is AU$280 per night from 30 Dec to 31 Dec
AU$280
30 Dec - 31 Dec
includes taxes & fees
Located in Grants Pass, this vacation home is on a river, a 1-minute drive from Rogue River and 8 minutes from Riverside Park.
Opens in a new windowThe River House with Views of the Famous Rogue River! No cleaning fees!
Home Theater - Gamer Ready!<br>Suite A

Home Theater - Gamer Ready!<br>Suite A

Grants Pass OR
The price is AU$288 per night from 8 Jan to 9 Jan
AU$288
8 Jan - 9 Jan 2026
includes taxes & fees
With a stay at this vacation home, you'll be centrally located in Grants Pass, just a 3-minute walk from Schmidt House Museum and 6 minutes by foot from Grants ...
Opens in a new windowHome Theater - Gamer Ready!<br>Suite A
Award Winning Britt Bungalow in the Historical Heart of Jacksonville Oregon

Award Winning Britt Bungalow in the Historical Heart of Jacksonville Oregon

Jacksonville OR
With a stay at this vacation home in Jacksonville (Jacksonville Historic District), you'll be within a 5-minute walk of Sarah Zigler Interpretive Trail and Jacksonville ...
Opens in a new windowAward Winning Britt Bungalow in the Historical Heart of Jacksonville Oregon
1907 Charmer, Perfect Downtown Location, So Clean!

1907 Charmer, Perfect Downtown Location, So Clean!

Ashland OR
A stay at this vacation home places you in the heart of Ashland, steps from Ashland Library and Oregon Cabaret Theatre.
Opens in a new window1907 Charmer, Perfect Downtown Location, So Clean!
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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.

Jacksonville Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Jacksonville vacation homes are the perfect way for you to wing it.

Holiday houses in Jacksonville let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Jacksonville in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Jacksonville adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Jacksonville with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Jacksonville vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Jacksonville Holiday Homes essential information

Accommodation
312 Holiday Homes
Lowest Price
AU$176
Highest Price
AU$855
Popular accommodation
Jacksonville Place, Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly, New house with king beds and 3 full bathrooms, New Downtown 3 Bedroom Upstairs Flat with views, East Main Downtown Bungalow , The River House with Views of the Famous Rogue River! No cleaning fees!, Home Theater - Gamer Ready!
Suite A, Award Winning Britt Bungalow in the Historical Heart of Jacksonville Oregon, 1907 Charmer, Perfect Downtown Location, So Clean!

Top trending 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 AU$176 per night from 1 Jan to 2 Jan
AU$176
1 Jan - 2 Jan 2026
includes taxes & fees
Located in Jacksonville, Wine Country Inn is in the historical district, within a 15-minute walk of Art Presence Art Center and Quady North.
Opens in a new windowWine Country Inn
The Lindsay Lodge & Restaurant

The Lindsay Lodge & Restaurant

2 out of 5
15100 Oregon 238 Jacksonville OR
The price is AU$351 per night from 29 Dec to 30 Dec
AU$351
29 Dec - 30 Dec
includes taxes & fees
Located in Jacksonville, The Lindsay Lodge & Restaurant is within a 5-minute drive of Applegate Library and Devitt Winery and Vineyards.
Opens in a new windowThe 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 AU$311 per night from 26 Jan to 27 Jan
AU$311
26 Jan - 27 Jan 2026
includes taxes & fees
A stay at The Orth House Inn by Remotion places you in the heart of Jacksonville, steps from Kharmic Creations and 3 minutes by foot from Quady North.
Opens in a new windowThe Orth House Inn by Remotion
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Magnolia Hotel

Magnolia Hotel

3 out of 5
245 North 5th Street Jacksonville OR
Fully refundableReserve now, pay when you stay
The price is AU$253 per night from 29 Dec to 30 Dec
AU$253
29 Dec - 30 Dec
includes taxes & fees
Located in Jacksonville (Jacksonville Historic District), Magnolia Hotel is within a 10-minute walk of Britt Pavilion and Jacksonville Cemetery.
Opens in a new windowMagnolia Hotel
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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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^Subject to availability and chosen travel dates.