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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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.
$240 nightly
The price is $244
Oct 2 - Oct 3
Total with taxes and fees
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, (238 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
$258 nightly
The price is $288
Oct 18 - Oct 19
Total with taxes and fees
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.
$250 nightly
The price is $279
Oct 5 - Oct 6
Total with taxes and fees
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.
$206 nightly
The price is $230
Oct 5 - Oct 6
Total with taxes and fees
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
$405 nightly
The price is $411
Oct 5 - Oct 6
Total with taxes and fees
Paschal Winery
A residential house with a front porch, a small garden with various plants and flowers, and a gravel driveway.

6. 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.
$194 nightly
The price is $196
Oct 6 - Oct 7
Total with taxes and fees
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.

7. 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
$235 nightly
The price is $264
Sep 30 - Oct 1
Total with taxes and fees
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
A house with a yellow front door, a blue door, and a garden with various flowers and plants.

8. Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (51 reviews)
"Good location and comfy beds!"
United States
Melissa L.
$208 nightly
The price is $233
Oct 15 - Oct 16
Total with taxes and fees
Downtown Mint
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, (129 reviews)
"Wonderful stay and will definitely do so again!!!"
United States
Kelly B.
$158 nightly
The price is $178
Oct 4 - Oct 5
Total with taxes and fees
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
A bedroom with a bed, a TV, a ladder, a mirror, a basket, and a door with a 'No Smoking' sign.

10. 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.
$171 nightly
The price is $195
Oct 14 - Oct 15
Total with taxes and fees
Rosewood Studio | Private Cottage Near Downtown
A blue house with a patio, a small table and chairs, and a hanging flower basket.

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
$256 nightly
The price is $260
Sep 30 - Oct 1
Total with taxes and fees
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
A two-story house with a front porch, a covered entryway, and a small front yard.

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)
"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
$304 nightly
The price is $322
Sep 30 - Oct 1
Total with taxes and fees
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 small house with a porch, a bench, and a tree with white blossoms.

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, (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.
$236 nightly
The price is $240
Sep 30 - Oct 1
Total with taxes and fees
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
A small, single-story house with a white picket fence, a purple front door, and a porch with white railings.

14. 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.
$287 nightly
The price is $310
Sep 30 - Oct 1
Total with taxes and fees
Historic Bradshaw House!
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.
$352 nightly
The price is $389
Sep 30 - Oct 1
Total with taxes and fees
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
A house with a window, a wooden fence, and a sign reading '160 C Street'.

16. Fireside Cottage in Downtown Jacksonville

Fireside Cottage in Downtown Jacksonville
Jacksonville Historic District
$223 nightly
The price is $249
Sep 30 - Oct 1
Total with taxes and fees
Fireside Cottage in Downtown Jacksonville
A house with a stone pathway, white picket fence, and a small porch.

17. 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.
$265 nightly
The price is $285
Oct 1 - Oct 2
Total with taxes and fees
Charming 1BR Cottage – Walk to Britt Gardens
A two-story house with a sloped roof, multiple windows, and a well-maintained garden.

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.

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.
$295 nightly
The price is $316
Oct 25 - Oct 26
Total with taxes and fees
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 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
$269 nightly
The price is $289
Oct 28 - Oct 29
Total with taxes and fees
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
$205 nightly
The price is $224
Oct 4 - Oct 5
Total with taxes and fees
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

Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek

8/10 Good
"If you are attending an Oregon Shakespeare Festival play, this property is beautifully located about a 10-minute walk from the festival grounds, various restaurants, and Lithia Park. My assigned room wasn't one of the best rooms as it had no balcony or view of the river, but it worked very well for me as I was walking to and from the festival grounds and my room was on the ground floor near an entrance to the play route. Covered parking was nice to have. Breakfast was very good, but always the same and served in a very nice room with access to a balcony overlooking the river so nice for summer or early fall. Tiny tubes of shampoo and other amenities worked fine if you were only staying a day but luckily were replenished daily."
J. 3-night trip
Posted 2 hours ago
Plaza Inn & Suites at Ashland Creek

Find out more about Ashland

Ashland Cottages information

Number of reviews
828
Accommodation
126 Cottages
Lowest Price
$178
Highest Price
$411

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between $178 and $411 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 3 miles 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 0.5 miles 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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