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

Jackson County Vacation Rentals

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Our top choices for Jackson County holiday rentals

A campfire, wooden chairs, and a bench in a forested area with a view of a bridge.

1. Union Creek Resort

Union Creek Resort
3.0 star property
Prospect
8.0 out of 10, Very good, (1,098 reviews)
"It was a great spot to stay to check out crater lake."
United States
Kameron
The price is RM343
RM352 total
includes taxes & fees
18 Oct - 19 Oct
Union Creek Resort
A spacious kitchen with a central island, bar stools, and a fireplace.

2. Paschal Winery

Paschal Winery
4.5 star property
Talent
9.8 out of 10, Exceptional, (19 reviews)
"Stunning scenery, great wine and food. Friendly, helpful people on site and the hot tub is blissfully perfect ❤️"
United States
Christine
The price is RM570
RM1,730 total
includes taxes & fees
14 Oct - 15 Oct
Paschal Winery
A deck with a fire pit, outdoor seating, and a view of the countryside.

3. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (11 reviews)
"The Grandview house and property far exceeded our expectations. We especially enjoying making meals together in the beautiful kitchen and reminiscing on the deck while taking in the spectacular views. We were fortunate to see lots of wildlife too. We hope to come back next year."
United States
Sonja
The price is RM834
RM1,672 total
includes taxes & fees
14 Oct - 15 Oct
Grandview of Ashland
A modern living room with a wooden floor, a sofa, a coffee table, and a kitchen area in the background.

4. The Rellik House and Winery

The Rellik House and Winery
3.5 star property
Central Point
9.4 out of 10, Exceptional, (6 reviews)
The price is RM792
RM1,509 total
includes taxes & fees
9 Nov - 10 Nov
The Rellik House and Winery
A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

5. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (10 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is RM526
RM1,110 total
includes taxes & fees
14 Oct - 15 Oct
Barclay Klum House by WanderLodges
A kitchen with a stainless steel sink, wooden cabinets, a black stove, and a window with curtains.

6. Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
The price is RM393
RM649 total
includes taxes & fees
14 Oct - 15 Oct
Rosewood Studio by WanderLodges
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

Starwood Sanctuary
3.0 star property
Medford
9.4 out of 10, Exceptional, (3 reviews)
"I was able to have early check in. The private bathroom off the main room was tiny. Coffee and cocoa were nice. The beds were comfy but the accent lights didn’t work and the shampoo dispenser was broken. Price and location were nice.. may book again.. spider webs outside 🤔😊"
United States
Erin
The price is RM526
RM1,138 total
includes taxes & fees
25 Oct - 26 Oct
Starwood Sanctuary
A spacious living room with a wooden floor, a dining table, a sofa, and a TV.

8. Rosewood Collective- House & Studio

Rosewood Collective- House & Studio
3.0 star property
Medford
The price is RM658
RM1,792 total
includes taxes & fees
14 Oct - 15 Oct
Rosewood Collective- House & Studio
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

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (5 reviews)
"Very cute cottage, 10 min walk to OSF theaters. It has everything you need - full kitchen, front room, and AC for the hot summers! Owner very kind. Will stay there again!"
United States
Robert
The price is RM555
RM933 total
includes taxes & fees
14 Oct - 15 Oct
Hanna's House by WanderLodges
A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

10. Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Had an amazing stay, thank you!"
United States
megan
The price is RM935
RM1,721 total
includes taxes & fees
25 Oct - 26 Oct
Savage Upon Siskiyou
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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Top Jackson County Hotel Reviews

Stratford Inn

Stratford Inn

10/10 Excellent
"An easy walk to the theaters and stores. If we needed anything, Safeway was across the street. Well maintained older property, clean and comfortable. The staff was helpful, courteous and informative. We plan on returning."
Dale 2-night trip
Posted 1 hour ago
Stratford Inn

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Holiday Apartments in Jackson County

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