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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Ashland cottages

A house with a driveway, a tree in the front yard, and a rainbow in the background.

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, (19 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 $191
CA $342 total
includes taxes & fees
Sep 29 - Sep 30
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
A house with a wooden deck, a stone wall, and a wooden fence.

2. The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (237 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
The price is CA $236
CA $410 total
includes taxes & fees
Oct 18 - Oct 19
The Ashland Cottage, walk to town
A modern living room with a grey sofa, a small table, and a basket on a white ottoman.

3. Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (74 reviews)
"Great location in the heart of downtown"
United States
John B.
The price is CA $210
CA $403 total
includes taxes & fees
Oct 5 - Oct 6
Courtside Cottage - WalkScore 93 - Dog Friendly
A residential house with a garage, a satellite dish, and a driveway.

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 CA $176
CA $330 total
includes taxes & fees
Oct 5 - Oct 6
Charming carriage house in Ashland near downtown
An outdoor patio with a grill, dining table, chairs, and string lights.

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 $170
CA $571 total
includes taxes & fees
Oct 8 - Oct 9
Paschal Winery
A bedroom with a bed, a TV, a ladder, a mirror, a basket, and a door with a 'No Smoking' sign.

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 $170
CA $295 total
includes taxes & fees
Sep 29 - Sep 30
Rosewood Studio | Private Cottage Near Downtown
A house with a yellow front door, a blue door, and a garden with various flowers and plants.

7. 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 $134
CA $316 total
includes taxes & fees
Oct 15 - Oct 16
Downtown Mint
A residential house with a front porch, a small garden with various plants and flowers, and a gravel driveway.

8. 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 $172
CA $276 total
includes taxes & fees
Oct 5 - Oct 6
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
A single-story house with a gabled roof, surrounded by a variety of plants and shrubs.

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

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
City Center Medford
9.6 out of 10, Exceptional, (48 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 $182
CA $374 total
includes taxes & fees
Sep 30 - Oct 1
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

10. 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, (129 reviews)
"Wonderful stay and will definitely do so again!!!"
United States
Kelly B.
The price is CA $139
CA $251 total
includes taxes & fees
Oct 4 - Oct 5
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
A two-story house with a front porch, a covered entryway, and a small front yard.

11. 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)
"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 CA $146
CA $456 total
includes taxes & fees
Sep 29 - Sep 30
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.
A blue house with a patio, a small table and chairs, and a hanging flower basket.

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, (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 $180
CA $373 total
includes taxes & fees
Sep 29 - Sep 30
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
A small, single-story house with a white picket fence, a purple front door, and a porch with white railings.

13. Historic Bradshaw House!

Historic Bradshaw House!
Jacksonville
10.0 out of 10, Exceptional, (70 reviews)
"We’ve stayed in Vrbo’s around the world and this is by far our favorite."
United States
Robert B.
The price is CA $179
CA $414 total
includes taxes & fees
Oct 4 - Oct 5
Historic Bradshaw House!
A small house with a porch, a bench, and a tree with white blossoms.

14. 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, (37 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 $195
CA $332 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
A residential property with a paved driveway leading to a front door, a wooden fence, and a small garden area.

15. 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 $224
CA $551 total
includes taxes & fees
Sep 30 - Oct 1
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
A house with a stone pathway, white picket fence, and a small porch.

16. Charming 1BR Cottage – Walk to Britt Gardens

Charming 1BR Cottage – Walk to Britt Gardens
Jacksonville
9.2 out of 10, Wonderful, (9 reviews)
"Location and interior was superb"
United States
Jonathan B.
The price is CA $172
CA $406 total
includes taxes & fees
Sep 29 - Sep 30
Charming 1BR Cottage – Walk to Britt Gardens
A two-story house with a sloped roof, multiple windows, and a well-maintained garden.

17. 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
9.0 out of 10, Wonderful, (7 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 $195
CA $447 total
includes taxes & fees
Oct 25 - Oct 26
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.
A house with a window, a wooden fence, and a sign reading '160 C Street'.

18. Fireside Cottage in Downtown Jacksonville

Fireside Cottage in Downtown Jacksonville
Jacksonville Historic District
The price is CA $185
CA $352 total
includes taxes & fees
Sep 29 - Sep 30
Fireside Cottage in Downtown Jacksonville
A bedroom with a fireplace, a bed with a headboard, a window, and a wall-mounted picture.

19. 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 CA $177
CA $412 total
includes taxes & fees
Sep 29 - Sep 30
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.
A cabin with a stone exterior, a porch with a red door, and a sign reading "The Cottage."

20. Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
10.0 out of 10, Exceptional, (2 reviews)
"Thank you, this was a very clean, attractive property with everything needed. Maricio was the host & he was very attentive, kind & quick to respond . I highly recommend this property, it’s in a nice area & fun places to explore. Thanks for a great visit!"
United States
Jayne
The price is CA $168
CA $317 total
includes taxes & fees
Oct 4 - Oct 5
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

Stratford Inn

Stratford Inn

10/10 Excellent
"Our room was great, a one bedroom with a king sized bed and a separate kitchen and living area, clean and newly renovated. Plenty of room to host a pre-dinner happy hour with friends. It is within walking distance of the Oregon Shakespeare theaters and downtown. The continental breakfast was fine with gluten free options."
Suzanne 3-night trip
Posted less than an hour ago
Stratford Inn

Find out more about Ashland

Ashland Cottages information

Number of reviews
827
Accommodation
126 Cottages
Lowest Price
CA $251
Highest Price
CA $571

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between CA $251 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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