A deer on a road with vegetation on the sides.

Search Cottages in Ashland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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

A house with a wooden deck, a stone wall, and a wooden fence.

1. 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 Ashland Cottage, walk to town
A modern living room with a grey sofa, a small table, and a basket on a white ottoman.

2. Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (72 reviews)
"Spacious, clean studio to explore Ashland!"
United States
Suzanne
Courtside Cottage - WalkScore 93 - Dog Friendly
A house with a driveway, a tree in the front yard, and a rainbow in the background.

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.
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
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.
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 €365
includes taxes & fees
2 Sept - 3 Sept
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.
Rosewood Studio | Private Cottage Near Downtown
A residential house with a front porch, a small garden with various plants and flowers, and a gravel driveway.

7. 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

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 €141
includes taxes & fees
14 Sept - 15 Sept
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
A house with a yellow front door, a blue door, and a garden with various flowers and plants.

9. Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (50 reviews)
"Good location and comfy beds!"
United States
Melissa L.
Downtown Mint
A cabin with a stone exterior, a porch with a red door, and a sign reading "The Cottage."

10. Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
The price is €204
includes taxes & fees
2 Oct - 3 Oct
Forest Cabin by Crater Lake & Klamath Falls
A single-story house with a gabled roof, surrounded by a variety of plants and shrubs.

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

13. 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 €297
includes taxes & fees
2 Sept - 3 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.
A bedroom with a fireplace, a bed with a headboard, a window, and a wall-mounted picture.

14. 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 €271
includes taxes & fees
2 Sept - 3 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.
A small house with a porch, a bench, and a tree with white blossoms.

15. 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 €205
includes taxes & fees
14 Sept - 15 Sept
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
A cabin with a stone exterior, a porch with a red door, and a sign reading "The Cottage."

16. 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
Forest Cabin by Crater Lake & Klamath Falls
A house with a window, a wooden fence, and a sign reading '160 C Street'.

17. Fireside Cottage in Downtown Jacksonville

Fireside Cottage in Downtown Jacksonville
Jacksonville Historic District
The price is €227
includes taxes & fees
2 Sept - 3 Sept
Fireside Cottage in Downtown Jacksonville
A residential property with a paved driveway leading to a front door, a wooden fence, and a small garden area.

18. 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 €339
includes taxes & fees
14 Sept - 15 Sept
The Williams - luxe 2-bedroom cottage w/onsite parking 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashland Hotel Reviews

Stratford Inn

Stratford Inn

8/10 Good
"The room was spotless, the bathroom sparkled. Wood floors, no icky carpeting. Soft towels, very nice Beekman 1802 products. The only things that weren’t quite right were: one of the washcloths in the bathroom had a stain that looked bad enough that it should have been retired. Even though it was probably recently washed, no one would want to put it on their face. No big deal to us. We couldn’t get comfortable on the bed no matter how we tried. Very unusual for me. I’m a pretty good sleeper but just couldn’t settle into the bed. Breakfast was great! Plenty of serve yourself options, a nice selection of breads, bagels, etc, along with cereals, yogurt toppings etc. Very organized and clean. Over all we’d definitely go back and maybe try a different room in hopes that our problems with the mattress were just a one time issue."
Janet 1-night trip
Posted 16 hours ago
Stratford Inn

Find out more about Ashland

Ashland Cottages information

Number of reviews
766
Accommodation
121 Cottages
Lowest Price
€141
Highest Price
€365

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between €141 and €365 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 121 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 holiday 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.