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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Ashland cottages

Exterior

1. 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 $188
CA $341 total
includes taxes & fees
Aug 12 - Aug 13
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Property grounds

2. 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 $188
CA $343 total
includes taxes & fees
Aug 22 - Aug 23
Charming carriage house in Ashland near downtown
Property grounds

3. The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (232 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
The price is CA $233
CA $399 total
includes taxes & fees
Aug 24 - Aug 25
The Ashland Cottage, walk to town
Smart TV, books

4. Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (71 reviews)
"Spacious, clean studio to explore Ashland!"
United States
Suzanne
The price is CA $245
CA $446 total
includes taxes & fees
Aug 24 - Aug 25
Courtside Cottage - WalkScore 93 - Dog Friendly
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 CA $194
CA $590 total
includes taxes & fees
Aug 18 - Aug 19
Paschal Winery
Exterior

6. 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, (124 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 $116
CA $225 total
includes taxes & fees
Aug 11 - Aug 12
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Exterior

7. Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (49 reviews)
"Good location and comfy beds!"
United States
Melissa L.
The price is CA $157
CA $336 total
includes taxes & fees
Sep 7 - Sep 8
Downtown Mint
1 bedroom, WiFi, bed sheets

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 CA $152
CA $274 total
includes taxes & fees
Aug 10 - Aug 11
Rosewood Studio | Private Cottage Near Downtown
Exterior

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

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
City Center Medford
9.6 out of 10, Exceptional, (42 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 $162
CA $348 total
includes taxes & fees
Aug 11 - Aug 12
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
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, (16 reviews)
"Everything was wonderful Will definitely stay again"
United States
Kellie P.
The price is CA $178
CA $279 total
includes taxes & fees
Sep 7 - Sep 8
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
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, (35 reviews)
"This cottage was perfect for our visit to historic Jacksonville. Check in was quick and easy. The property was minutes from town yet had a comfortable feel of being in the countryside. The hosts responded quickly to our inquiries. They were kind enough to quickly return a valuable item I left. Elizabeth's Cottage was perfect for our visit. Excellent choice for a lovely area."
United States
Donald F.
The price is CA $195
CA $389 total
includes taxes & fees
Aug 17 - Aug 18
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Exterior

12. Charming Jacksonville Studio with AC • Easy Walk to Town & Britt Festival

Charming Jacksonville Studio with AC • Easy Walk to Town & Britt Festival
Jacksonville, OR
10.0 out of 10, Exceptional, (2 reviews)
"We absolutely loved our stay. The host was friendly and totally on it. The home was clean and super comfortable. I definitely recommend staying here and will definitely come back. The photos honestly don’t do the place justice."
United States
Jason C.
The price is CA $125
CA $254 total
includes taxes & fees
Aug 31 - Sep 1
Charming Jacksonville Studio with AC • Easy Walk to Town & Britt Festival
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)
"Clean sweet comfortable and well priced"
United States
Linda C.
The price is CA $194
CA $331 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Exterior

14. 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, (5 reviews)
"So easy to get in and out. Convenient to everything we did in the valley. Exactly as advertised. Great views and quiet location. Will definitely book again when in town. "
United States
Marc A.
The price is CA $215
CA $430 total
includes taxes & fees
Aug 17 - Aug 18
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.
House (0 Bedroom) | Interior

15. Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
The price is CA $152
CA $297 total
includes taxes & fees
Aug 11 - Aug 12
Forest Cabin by Crater Lake & Klamath Falls
Exterior

16. Fireside Cottage in Downtown Jacksonville

Fireside Cottage in Downtown Jacksonville
Jacksonville Historic District
The price is CA $182
CA $339 total
includes taxes & fees
Aug 10 - Aug 11
Fireside Cottage in Downtown Jacksonville
Exterior

17. 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 $243
CA $572 total
includes taxes & fees
Aug 10 - Aug 11
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
Exterior

18. 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 $109
CA $304 total
includes taxes & fees
Aug 11 - Aug 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

Prospero's Flagship Inn

Prospero's Flagship Inn

8/10 Good
"Good value for the money! Clean and well maintained."
Rebecca 2-night trip
Posted 4 hours ago
Prospero's Flagship Inn

Find out more about Ashland

Ashland Cottages information

Number of reviews
666
Accommodation
126 Cottages
Lowest Price
CA $225
Highest Price
CA $590

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between CA $225 and CA $590 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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