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Our top choices for Ashland cottages

1. The Ashland Cottage, walk to town
The Ashland Cottage, walk to townSiskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (241 reviews)
The price is CA $177
CA $325 total
includes taxes & fees
Nov 8 - Nov 9

2. Courtside Cottage - WalkScore 93 - Dog Friendly
Courtside Cottage - WalkScore 93 - Dog FriendlyHistoric Railroad District
10.0 out of 10, Exceptional, (77 reviews)
The price is CA $142
CA $287 total
includes taxes & fees
Nov 30 - Dec 1

3. Charming carriage house in Ashland near downtown
Charming carriage house in Ashland near downtownSkidmore Academy Historic District
10.0 out of 10, Exceptional, (14 reviews)
The price is CA $160
CA $292 total
includes taxes & fees
Nov 9 - Nov 10

4. Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )Ashland
10.0 out of 10, Exceptional, (19 reviews)
The price is CA $189
CA $314 total
includes taxes & fees
Nov 30 - Dec 1

5. Paschal Winery
Paschal WineryTalent
9.8 out of 10, Exceptional, (19 reviews)
The price is CA $183
CA $584 total
includes taxes & fees
Nov 10 - Nov 11

6. Downtown Mint
Downtown MintMedford
10.0 out of 10, Exceptional, (52 reviews)
The price is CA $102
CA $261 total
includes taxes & fees
Nov 8 - Nov 9

7. Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot TubCentral Point
9.8 out of 10, Exceptional, (129 reviews)
The price is CA $137
CA $237 total
includes taxes & fees
Nov 11 - Nov 12

8. Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
Peaceful Countryside Stay with Scenic Views- 5 minutes to JacksonvilleCentral Point
10.0 out of 10, Exceptional, (19 reviews)
The price is CA $170
CA $264 total
includes taxes & fees
Nov 17 - Nov 18

9. Forest Cabin by Crater Lake & Klamath Falls
Forest Cabin by Crater Lake & Klamath FallsKlamath Falls
10.0 out of 10, Exceptional, (2 reviews)
The price is CA $167
CA $314 total
includes taxes & fees
Nov 11 - Nov 12

10. Rosewood Studio | Private Cottage Near Downtown
Rosewood Studio | Private Cottage Near DowntownMedford
8.0 out of 10, Very good, (1 review)
The price is CA $119
CA $222 total
includes taxes & fees
Nov 15 - Nov 16

11. Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.Central Point
9.6 out of 10, Exceptional, (40 reviews)
The price is CA $175
CA $347 total
includes taxes & fees
Nov 11 - Nov 12

12. Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.
Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.Jacksonville Historic District
9.8 out of 10, Exceptional, (85 reviews)
The price is CA $117
CA $387 total
includes taxes & fees
Nov 8 - Nov 9

13. Historic Bradshaw House!
Historic Bradshaw House!Jacksonville
10.0 out of 10, Exceptional, (71 reviews)
The price is CA $162
CA $348 total
includes taxes & fees
Nov 9 - Nov 10

14. Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.
Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.Jacksonville
9.6 out of 10, Exceptional, (5 reviews)
The price is CA $162
CA $366 total
includes taxes & fees
Nov 10 - Nov 11

15. Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville. Charm, convenience & budget friendly.
Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville. Charm, convenience & budget friendly.Central Point
8.8 out of 10, Excellent, (8 reviews)
The price is CA $170
CA $395 total
includes taxes & fees
Nov 15 - Nov 16

16. Charming 1BR Cottage – Walk to Britt Gardens
Charming 1BR Cottage – Walk to Britt GardensJacksonville
9.2 out of 10, Wonderful, (9 reviews)
The price is CA $162
CA $366 total
includes taxes & fees
Nov 10 - Nov 11

17. Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to JacksonvilleJacksonville
9.8 out of 10, Exceptional, (38 reviews)
The price is CA $179
CA $304 total
includes taxes & fees
Nov 21 - Nov 22

18. Forest Cabin by Crater Lake & Klamath Falls
Forest Cabin by Crater Lake & Klamath FallsKlamath Falls
9.0 out of 10, Wonderful, (6 reviews)
The price is CA $122
CA $304 total
includes taxes & fees
Nov 9 - Nov 10
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.
Learn more about Ashland
World-class Shakespeare performances unfold in outdoor theatres surrounded by mountain views from June through October. Lithia Park's trails wind along Ashland Creek, perfect for morning walks before browsing the downtown galleries and craft breweries.



























































