Jacksonville Rentals

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49 Houses

Beautiful Luxury Cottage "The Quarters" - Walk to it All !

Jacksonville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$228

The Lily Pad

Jacksonville house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$228

The Tigers Den

Jacksonville cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$228

Beautiful Home on the Applegate River - Newly Remodeled

Jacksonville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$453

Mountain Retreat!

Jacksonville house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

Price per night from

$912

Beautiful Home on the Applegate River - Surrounded by Wineries

Jacksonville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$516

Great rentals within 20 miles that match your search

Cheerful new guest house

Medford house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$138

Katias house

Medford house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 13

Price per night from

$287

Sunshine Studio

Medford studio

  • Studio
  • 1 bathroom
  • sleeps 3

Price per night from

$115

Skyfall Landing in Southern Oregon

Eagle Point house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$224

Lotus House

Medford house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$224

Brookdale Meadows Farmhouse Cutie

Medford house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$183

Private Tiny Home with Sauna and Soaking tubs

Rogue River house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$193

Price per night from

$344

The High Street Cottage An Artists' Garden Cottage

Ashland cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 14 minutes

Price per night from

$218

The Terra Cottage Inn a beautiful Luxury Apartment

Ashland cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Perfect!” We just returned from our annual trip to ashland, mainly for OSF. After previously staying in B&B;'s we chose to find a rental house for this week. I did a bunch of research and what struck us about the Terra Cottage Inn was the outdoor kitchen. Since my wife I like to cook, we though this would be the place. I will say this is one place where the pictures do not do the property justice. First, the outdoor kitchen: it is the best! The grill, the stove, the sink, the refrigerator, the incredible clay pottery that one of the proprietors (Elizabeth) and the table and benches that the other proprietor (Mark) made make it a perfect spot. We took advantage of this spot to have several dinners and with the lounge chairs, it is perfect for morning coffee.It should be noted that the Terra Cottage Inn is part of a beautiful property that includes one other rental house and the owners house. Besides the outdoor kitchen, there is a Koi pond, a garden (from which you can pick anything from), a hammock, and outdoor shower (if you want to use it) and Elizabeth's Pottery Studio and Mark's art Studios. The have decorated the whole property with great lights and artistic touches everywhere. Terra Cottage Inn is in it's own building up a flight stairs(nothing but storage down below). It is not large, but perfect for a vacation rental. During our visit the temps in ashland were above 100 degrees, but the air conditioning kept is nice and cool. The kitchen is well stocked and the living room furniture is very comfortable.The linens in the bedroom are great and the queen bed is comfortable. They also provide great bathrobes! There is a second bedroom with two twin beds (which we didn't need to use). Bathroom has good water pressure and they provided almost everything you could need (shampoo, soap. lotion etc...). The inside space is not huge, but very comfortable, when you add in all the magical outdoor areas this is an a+ space and we will be back every year.

Responds fast! avg. 2 hours 14 minutes

Price per night from

$207

“Fabulous place to stay!” We recently stayed in this cottage for 3 nights and we really enjoyed ourselves. The short walk to the plaza and theaters was ideal, but we were most impressed by how clean and well-maintained the cottage was. The cottage is on the property of the Hersey House Bed and Breakfast Inn and the hosts were very welcoming, and they deliver a morning continental breakfast tray. We especially liked the warm raspberry crumble with sweet cream and it was nice because we enjoyed 3 breakfast trays and each morning we were served something different. We really like the cottage and it was super easy with our kids because there were two bedrooms and it was handy to have the kitchen. We will definitely be back!

Price per night from

$344

Lotus Studio II

Medford guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$114

Perfect vacation cottage

Ashland cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$327

Nancy's Garden Cottage The Indigo

Ashland cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$144

Stone's Throw Bungalow - Licensed, Private Garden

Ashland studio

  • Studio
  • 1 bathroom
  • sleeps 2

Price per night from

$184

Luxurious Home near Downtown Ashland and Theaters

Ashland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$441

Walk to Downtown/Theaters from this Charming Home

Ashland cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$338

Oberon -Second Spring Property 1-3 Bedroom Luxury

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$224

Chamomile Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$258

Calla Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$258

Daisy Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$258

Iris Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$258

Jasmine Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$258

Marigold Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$258

Rose Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$258

Pomegranate Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$258

Viola Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$258

Hargadine House: The Carriage House

Ashland studio

  • Studio
  • 1 bathroom
  • sleeps 2

Price per night from

$274

Guest room with private bath in a Cozy Log Cabin!

Talent private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$67

2nd Street Cottages, HERITAGE HOUSE

Ashland cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$567

Carlisle Garden Suites - Calla Suite

Ashland cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$235

Carlisle Garden Suites - Chamomile

Ashland cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$235

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