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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Ashland cottages

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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.
The price is CA $242
CA $431 total
includes taxes & fees
Oct 5 - Oct 6
Courtside Cottage - WalkScore 93 - Dog Friendly
Exterior

2. 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 CA $186
CA $334 total
includes taxes & fees
Sep 14 - Sep 15
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Property grounds

3. 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 CA $177
CA $325 total
includes taxes & fees
Sep 14 - Sep 15
Charming carriage house in Ashland near downtown
Dream Cottage 1 | Terrace/patio

4. 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 CA $179
CA $571 total
includes taxes & fees
Sep 10 - Sep 11
Paschal Winery
Exterior

5. 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.
The price is CA $164
CA $269 total
includes taxes & fees
Sep 21 - Sep 22
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
1 bedroom, WiFi, bed sheets

6. 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 CA $149
CA $268 total
includes taxes & fees
Sep 10 - Sep 11
Rosewood Studio | Private Cottage Near Downtown
Exterior

7. 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 CA $178
CA $365 total
includes taxes & fees
Sep 9 - Sep 10
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
Exterior

8. 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 CA $112
CA $219 total
includes taxes & fees
Sep 14 - Sep 15
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Exterior

9. Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (51 reviews)
"Good location and comfy beds!"
United States
Melissa L.
The price is CA $131
CA $308 total
includes taxes & fees
Oct 5 - Oct 6
Downtown Mint
House (0 Bedroom) | Interior

10. Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
The price is CA $151
CA $294 total
includes taxes & fees
Sep 11 - Sep 12
Forest Cabin by Crater Lake & Klamath Falls
Exterior

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, (39 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 CA $174
CA $355 total
includes taxes & fees
Oct 5 - Oct 6
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Exterior

12. 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 CA $185
CA $322 total
includes taxes & fees
Sep 21 - Sep 22
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Exterior

13. Fireside Cottage in Downtown Jacksonville

Fireside Cottage in Downtown Jacksonville
Jacksonville Historic District
The price is CA $182
CA $345 total
includes taxes & fees
Sep 9 - Sep 10
Fireside Cottage in Downtown Jacksonville
Exterior

14. 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 CA $223
CA $537 total
includes taxes & fees
Sep 14 - Sep 15
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
Exterior

15. 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 CA $108
CA $301 total
includes taxes & fees
Sep 11 - Sep 12
Forest Cabin by Crater Lake & Klamath Falls
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

Ashland Springs Hotel

Ashland Springs Hotel

8/10 Good
"Ashland Springs Hotel is the best-located hotel in Ashland for purposes of attending the Oregon Shakespeare Festival. Staff is uniformly helpful and the amenities (including modest breakfast for $5,) are great. Any issues are merely quibbles (e.g. breakfast offerings could be more diverse, coffee pot should be reliably restocked on mezzanine). Overall, great stay! Expensive, but worth it!"
David 5-night trip
Posted 3 hours ago
Ashland Springs Hotel

Find out more about Ashland

Ashland Cottages information

Number of reviews
447
Accommodation
126 Cottages
Lowest Price
CA $219
Highest Price
CA $571

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between CA $219 and CA $571 per night. These properties offer a chance to get in touch with nature — at a price you can afford. These prices were 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.
What are the best cottages in Ashland?
Ashland has multiple cottages with a total average guest review rating of 9.7. Oak Street Cottages is a good option if you're into nature and an easy-breezy pace. Guests of this 3-star stay will enjoy amenities such as a fireplace and a barbecue grill. The Retreat At Oak Knoll ~ Pet Friendly is another popular pick. This 4-star cottage features a fireplace and a barbecue grill.
How many cottages are there in Ashland?
Pack your suitcase and pick from 126 cottages in Ashland. Longing for a place where you can relax and connect with nature? Expedia will help you find your ideal retreat in only a click or two.
Are there any family-friendly cottages in Ashland?
A trip with the family in Ashland is a cinch at Oak Street Cottages. With conveniences including a barbecue grill and a picnic area, you'll have all the comforts of home at this 3-star cottage. The Retreat At Oak Knoll ~ Pet Friendly is another family-friendly stay where you and your crew can escape the daily grind of the city. This cottage has a 4-star rating and amenities including a fireplace and a barbecue grill. Once you've checked in and dropped off your things, there are lots of family-friendly attractions to visit in and around Ashland. ScienceWorks Hands-On Museum and Mount Ashland Ski Area guarantee fun for young and old.
Are there any 5-star cottages in Ashland?
Ashland doesn't have any 5-star cottages — but you and the family can still enjoy a stylish getaway! Why not have a look at The Retreat At Oak Knoll ~ Pet Friendly? Located approximately 5 kilometres from downtown, this 4-star retreat features a living room and a garden. C' Street Station - Short Walk To Osf is another fantastic 4-star pick just 0.80 kilometres from central Ashland. It provides a relaxed vibe close to nature as well as conveniences like a fireplace and free WiFi.
Why book your cottage in Ashland with Expedia?
Expedia has some superb cottages in Ashland, so get set for a memorable vacation close to nature. If you have a certain budget, click on how much you want to spend and the preferred star rating of your property. Or, use our handy filters to search for cottages with a pool or free WiFi. We'll help you find the right fit whatever your style of travel or plans.
How can I find cheap cottages in Ashland?
The easiest way to track down cheap cottages in Ashland is with Expedia's convenient filter tool. Refine your search results by budget, star rating and amenities to grab unbeatable bargains in just a few clicks.
What is there to do in Ashland near my cottage?
Whatever you're interested in, Ashland has plenty to keep you entertained. Emigrant Lake, Angus Bowmer Theatre and ScienceWorks Hands-On Museum are on many visitors' sightseeing plans. Don't miss North Mountain Park, Mount Ashland Ski Area and Allen Elizabethan Theatre either. With Expedia's Ashland hotel deals, you can see more fantastic attractions like these with the cash you save.

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