Jacksonville Vacation Rentals, Houses & More


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Great rentals within 20 miles that match your search

1 / 9

Oak Street Cottages~Tower Townhouse ~ 1.5 Blocks to Oregon Shakespeare Festival!

  • 2
  • 8
  • 2 nights min

$260

Details

1 / 21

Steps to theatres, shopping, dining, nightlife...

  • 4
  • 8
  • 1 night min

$417

Details

1 / 13

Bel Canto ~ Ashland Hillside ~ Five Minutes from OSF

  • 2
  • 4
  • 2 nights min

$174

Details

1 / 14

Historic Craftsman in Downtown Medford

  • 2
  • 3
  • 2 nights min

$138

Details

1 / 16

'1900' House ~ Downtown Ashland - Near Oregon Shakespeare Festival ~ Sleeps 8

  • 3
  • 8
  • 2 nights min

$293

Details

1 / 9

'1900' Guest House ~ Downtown Ashland ~ Near Oregon Shakespeare Festival!

  • 1
  • 2
  • 2 nights min

$125

Details

1 / 9

Tuscan Retreat on the Rogue River (Sleeps 4)

  • 2
  • 4
  • 2 nights min

$293

Details

1 / 17

The Dream Cottage at Paschal Winery ~ Sleeps 4

  • 1
  • 4
  • 2 nights min

$194

Details

1 / 18

Best Location, Impeccable Style and Ultimate Comfort

  • 2
  • 4
  • 3 nights min

$120

Details

1 / 15

Juliet

  • 2
  • 4
  • 2 nights min

$214

Details

1 / 19

Remote Woodland Family Friendly Cottage near Town

  • 1
  • 8
  • 2 nights min

$100

Details

1 / 9

The Cottage at Grizzly Peak Winery - Sleeps 4

  • 1
  • 4
  • 2 nights min

$196

Details

1 / 9

Butler's Quarters ~ Downtown Ashland (Private Entry)

  • Studio
  • 2
  • 1 night min

$145

Details

1 / 9

Oak Street Cottages ~ Hideaway ~ 1.5 Blocks to Oregon Shakespeare Festival!

  • 2
  • 6
  • 2 nights min

$221

Details

1 / 10

The High Street Cottage An Artists' Garden Cottage

  • 2
  • 4
  • 2 nights min

$166

Details

1 / 10

The Terra Cottage Inn a beautiful Luxury Apartment

  • 2
  • 4
  • 2 nights min

$160

Details

1 / 11

RedTail Inn ~ The "Red" McCall Suite ~ Sleeps Six

  • 2
  • 6
  • 2 nights min

$346

Details

1 / 29

Riverfront oasis with pool

  • 2
  • 6
  • 2 nights min

$159

Details

1 / 23

Stone's Throw Bungalow - Licensed, Private Garden

  • Studio
  • 2
  • 2 nights min

$134

Details

1 / 25

Private Mountain View Suite

  • 1
  • 5
  • 1 night min

$95

Details

1 / 7

Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In The Heart Of Ashland

  • 1
  • 3
  • 2 nights min

$298

Details

1 / 5

Tina's Luxury Studio II

  • 3
  • 2 nights min

$89

Details

1 / 25

Perfect vacation cottage

  • 2
  • 6
  • 2 nights min

$283

Details

1 / 34

Waverly Cottage 1898 Historic Victorian

  • 2
  • 4
  • 1 night min

$144

Details

1 / 16

Relaxing Suburban Home with Large Yard

  • 3
  • 6
  • Min stay varies

$158

Details

1 / 8

Walk to Downtown/Theaters from this Charming Home

  • 2
  • 6
  • 2 nights min

$194

Details

1 / 12

Romeo

  • 2
  • 4
  • 2 nights min

$214

Details

1 / 24

Affordable, Private Retreat for 2 with Great Views

  • 1
  • 2
  • 3 nights min

$144

Details

1 / 7

Tina's Luxury Studio I

  • 3
  • 2 nights min

$79

Details

1 / 20

Abigail's Cottage, 10-min. walk to plaza/theaters

  • 2
  • 6
  • 2 nights min

$184

Details

1 / 9

Nancy's Garden Cottage

  • 1
  • 2
  • 30 nights min

$83

Details

1 / 14

Luxurious Home near Downtown Ashland and Theaters

  • 3
  • 9
  • 2 nights min

$283

Details

1 / 26

Private and Luxurious Cottage Constructed in 2015 with High End Amenities

  • 1
  • 2
  • 30 nights min

$100

Details

1 / 13

Oak Street Cottages ~ Oak Lawn ~ 1.5 Blocks to Oregon Shakespeare Festival!

  • 2
  • 6
  • 2 nights min

$219

Details

1 / 22

Pioneer House ~ One Block from OSF

  • 3
  • 8
  • 1 night min

$323

Details

1 / 15

Private Entrance. Clean. Comfortable.

  • 1
  • 4
  • 1 night min

$95

Details

1 / 14

Plymale Cottage, Bed & Biscotti

  • 2
  • 4
  • 1 night min

$145

Details

1 / 8

Center of Town!

  • 2
  • 2
  • 7 nights min

$72

Details

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