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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Ashland cottages

Living area

1. Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (72 reviews)
"Great location in the heart of downtown"
United States
John B.
Courtside Cottage - WalkScore 93 - Dog Friendly
Property grounds

2. The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (233 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
The price is AU$391
includes taxes & fees
7 Sept - 8 Sept
The Ashland Cottage, walk to town
Exterior

3. 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, (18 reviews)
"Wonderful location, well appointed place very quiet, beautifully located, and very special place on the farm"
United States
Greg M.
The price is AU$345
includes taxes & fees
4 Oct - 5 Oct
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Property grounds

4. Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown
Skidmore Academy Historic District
10.0 out of 10, Exceptional, (13 reviews)
"Lovely stay. "
United States
Cyndy K.
The price is AU$373
includes taxes & fees
1 Oct - 2 Oct
Charming carriage house in Ashland near downtown
Dream Cottage 1 | Terrace/patio

5. 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 AU$579
includes taxes & fees
24 Sept - 25 Sept
Paschal Winery
House (0 Bedroom) | Interior

6. Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
The price is AU$297
includes taxes & fees
10 Sept - 11 Sept
Forest Cabin by Crater Lake & Klamath Falls
Exterior

7. Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (50 reviews)
"Good location and comfy beds!"
United States
Melissa L.
Downtown Mint
Room

8. Rosewood Studio | Private Cottage Near Downtown

Rosewood Studio | Private Cottage Near Downtown
Medford
8.0 out of 10, Very good, (1 review)
"Location was as advertised."
United States
william L.
The price is AU$276
includes taxes & fees
13 Sept - 14 Sept
Rosewood Studio | Private Cottage Near Downtown
Exterior

9. Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Central Point
9.8 out of 10, Exceptional, (126 reviews)
"We had such an amazing relaxing weekend at this little hidden jewel, tucked away in Central Point. "
United States
Chris A.
The price is AU$225
includes taxes & fees
14 Sept - 15 Sept
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Exterior

10. Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville

Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
Central Point
10.0 out of 10, Exceptional, (18 reviews)
"Everything was wonderful Will definitely stay again"
United States
Kellie P.
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
Exterior

11. HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
City Center Medford
9.8 out of 10, Exceptional, (46 reviews)
"Amazing location and the interior design was fabulous! Has everything you need and my dog had a great time too! All around awesome place, would highly recommend."
United States
Houda
The price is AU$429
includes taxes & fees
6 Sept - 7 Sept
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
Exterior

12. 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, (38 reviews)
"Sweet little place that was very clean. Owners were pretty much no contact which for us was nice, I'm sure it would have been different if there was an issue. The bridge you cross right after the gate was a bit scary to cross with your vehicle but it held up fine with two vehicles."
United States
Amanda
The price is AU$370
includes taxes & fees
8 Sept - 9 Sept
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Exterior

13. 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 Jacksonville
Jacksonville
9.8 out of 10, Exceptional, (36 reviews)
"Perfect spot for a solo traveler or a couple. Well-appointed and the property amenities were a nice touch."
United States
Nikki F.
The price is AU$331
includes taxes & fees
7 Sept - 8 Sept
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Exterior

14. 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, (84 reviews)
"What an adorable cottage. It’s right in town but on a quiet street. It had every amenity that we needed. I would very highly recommend and would stay here again"
United States
Richard
The price is AU$495
includes taxes & fees
14 Sept - 15 Sept
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.
Interior

15. 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, (4 reviews)
"Excellent location. The house was comfortable and had everything we needed."
United States
Christopher
The price is AU$429
includes taxes & fees
8 Sept - 9 Sept
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.
Exterior

16. The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville

The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
Jacksonville Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful place and great location"
United States
darren t.
The price is AU$544
includes taxes & fees
6 Sept - 7 Sept
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
Exterior

17. Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
Klamath Falls
9.0 out of 10, Wonderful, (6 reviews)
"The cabin is quiet and the kitchen is great for meals. We slept well and enjoyed the calm."
United States
Jo
The price is AU$306
includes taxes & fees
17 Sept - 18 Sept
Forest Cabin by Crater Lake & Klamath Falls
Exterior

18. Fireside Cottage in Downtown Jacksonville

Fireside Cottage in Downtown Jacksonville
Jacksonville Historic District
The price is AU$397
includes taxes & fees
6 Sept - 7 Sept
Fireside Cottage in Downtown Jacksonville
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 Ashland Hotel Reviews

Prospero's Flagship Inn

Prospero's Flagship Inn

8/10 Good
"If you just need a place to sleep, this wad good. It was quiet, it had a microwave and a fridge. It has a great little coffee shop within walking distance. It was cool that after hours they have a tall like tv screen with a live person to help you check in and gives you your room key from the machine below."
Timothy 2-night trip
Posted 2 hours ago
Prospero's Flagship Inn

Find out more about Ashland

Ashland Cottages information

Number of reviews
766
Accommodation
126 Cottages
Lowest Price
AU$225
Highest Price
AU$579

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between AU$225 and AU$579 per night. These retreats offer a chance to soak up nature's beauty — at a price you can afford. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Ashland?
You'll find 126 cottages in Ashland. No matter if you're travelling with the kids or planning a weekend retreat with your buddies, Expedia can help you find the perfect place to reacquaint yourself with nature.
What is there to do in Ashland near my cottage?
You'll find loads of terrific things that'll fill up your itinerary in Ashland. Explore leading attractions like Oregon Shakespeare Festival, Mount Ashland Ski Area and Oregon Cabaret Theatre. Allen Elizabethan Theatre, Thomas Theatre and Angus Bowmer Theatre are other must-see's.

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