Jackson County Holiday Homes from Rp3.027.493: Search Top Rental Houses in Jackson County

A river flowing through a forest with dense trees and a fallen log in the water.

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Our top choices for Jackson County holiday homes

A deck with a fire pit, outdoor seating, and a view of the countryside.

1. Grandview of Ashland

Ashland

Sonja

Rp7.242.622 total

includes taxes & fees

13 Sept - 14 Sept

A modern living room with a wooden floor, a sofa, a coffee table, and a kitchen area in the background.

2. The Rellik House and Winery

Central Point

Kimberlee

Rp7.237.233 total

includes taxes & fees

2 Sept - 3 Sept

A kitchen with a stainless steel sink, wooden cabinets, a black stove, and a window with curtains.

3. Rosewood Studio by WanderLodges

Medford

Rp3.027.493 total

includes taxes & fees

31 Aug - 1 Sept

A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

4. Barclay Klum House by WanderLodges

Ashland

Melissa

Rp5.020.698 total

includes taxes & fees

31 Aug - 1 Sept

A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

5. Savage Upon Siskiyou

Siskiyou-Hargadine Historic District

megan

Rp7.457.070 total

includes taxes & fees

31 Aug - 1 Sept

An outdoor patio with a stone fireplace, wooden seating, and a view of the surrounding landscape.

6. Meadowsweet Farm by WanderLodges

Medford

Rp9.814.262 total

includes taxes & fees

31 Aug - 1 Sept

A modern living room with a grey sofa, wooden flooring, a flat-screen TV, a desk with a chair, and a patterned rug.

7. Starwood Sanctuary

Medford

Erin

Rp4.930.374 total

includes taxes & fees

7 Sept - 8 Sept

A spacious living room with a wooden floor, a dining table, a sofa, and a TV.

8. Rosewood Landing- Hot Tub- Sauna

Medford

Rp6.968.609 total

includes taxes & fees

6 Sept - 7 Sept

A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

9. Hanna's House by WanderLodges

Historic Railroad District

David

Rp4.716.069 total

includes taxes & fees

10 Sept - 11 Sept

A modern kitchen with wooden beams, a dining area with a rug, and a large island.

10. The Mountain Ave House by WanderLodges

Ashland

Joyce

Rp6.095.858 total

includes taxes & fees

31 Aug - 1 Sept

11. Rosewood Collective- House & Studio

Medford

Rp8.624.675 total

includes taxes & fees

31 Aug - 1 Sept

12. Quail Run River View Cottage

Jacksonville

A living room with a brick fireplace, wooden furniture, and a ladder against the wall.

13. Jville Gem- Walk downtown

Jacksonville

A spacious bedroom with a large bed, a fireplace, and a green sofa in a well-lit room with large windows.

14. Cottage Eleven in Jacksonville

Jacksonville

A small, single-story house with a front porch, a white picket fence, and a well-maintained lawn.

15. Cottage Nine in Jacksonville

Jacksonville Historic District

"Loved my little cottage! When I finally got into it everything was great. There are a few tweaks I would add—bigger coffee cups as the coffee maker over brews the ones provided….the creamers had gone bad (the non-flavored ones) and there are no spoons provided. It needs a bath mat or towel for the floor for after showering or bathing in the tub and a heavier duvet and extra throw blanket for the couch would be nice as the nights are a little chilly and if you are traveling solo it’s nice to...

Diane