A deer on a road with vegetation on the sides.

Search Ashland Cottage Accommodations

  • 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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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, (241 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
The price is AU$412
includes taxes & fees
26 Oct - 27 Oct
The Ashland Cottage, walk to town
A residential house with a garage, a satellite dish, and a driveway.

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 AU$333
includes taxes & fees
27 Oct - 28 Oct
Charming carriage house in Ashland near downtown
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, (77 reviews)
"Excellent stay. Very responsive host. Would come back"
United States
Scott N.
The price is AU$387
includes taxes & fees
1 Nov - 2 Nov
Courtside Cottage - WalkScore 93 - Dog Friendly
An outdoor patio with a grill, dining table, chairs, and string lights.

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 AU$581
includes taxes & fees
28 Oct - 29 Oct
Paschal Winery
Exterior

5. 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 AU$259
includes taxes & fees
20 Oct - 21 Oct
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.

6. Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (52 reviews)
"Good location and comfy beds!"
United States
Melissa L.
The price is AU$317
includes taxes & fees
2 Nov - 3 Nov
Downtown Mint
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.
The price is AU$289
includes taxes & fees
25 Oct - 26 Oct
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.

8. 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 AU$381
includes taxes & fees
25 Oct - 26 Oct
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
A bedroom with a bed, a TV, a ladder, a mirror, a basket, and a door with a 'No Smoking' sign.

9. 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 AU$266
includes taxes & fees
23 Oct - 24 Oct
Rosewood Studio | Private Cottage Near Downtown
A blue house with a patio, a small table and chairs, and a hanging flower basket.

10. 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)
"Lovely cottage with all the amenities in the countryside with beautiful views down a quiet lane. Perfect for our stay to visit Jacksonville and easy access to Medford airport."
United States
Vanessa C.
The price is AU$372
includes taxes & fees
21 Oct - 22 Oct
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.

11. 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 AU$402
includes taxes & fees
19 Oct - 20 Oct
Historic Bradshaw House!
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
The price is AU$426
includes taxes & fees
19 Oct - 20 Oct
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 house with a stone pathway, white picket fence, and a small porch.

13. 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 AU$408
includes taxes & fees
19 Oct - 20 Oct
Charming 1BR Cottage – Walk to Britt Gardens
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 AU$394
includes taxes & fees
19 Oct - 20 Oct
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 two-story house with a sloped roof, multiple windows, and a well-maintained garden.

15. 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 AU$444
includes taxes & fees
25 Oct - 26 Oct
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 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
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 AU$323
includes taxes & fees
23 Oct - 24 Oct
Forest Cabin by Crater Lake & Klamath Falls
A cabin with a stone exterior, a porch with a red door, and a sign reading "The Cottage."

17. 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 AU$371
includes taxes & fees
18 Nov - 19 Nov
Forest Cabin by Crater Lake & Klamath Falls
A residential property with a paved driveway leading to a front door, a wooden fence, and a small garden area.

18. The Williams - Luxury 2-bedroom with On-Site Parking in Downtown Jacksonville

The Williams - Luxury 2-bedroom with On-Site Parking in Downtown Jacksonville
Jacksonville Historic District
10.0 out of 10, Exceptional, (3 reviews)
"Lovely, comfortable stay, within easy walking distance to the Main Street of Jacksonville and all that has to offer. Very clean, beautifully decorated and comfortable. I highly recommend!"
United States
Janice C.
The price is AU$546
includes taxes & fees
21 Oct - 22 Oct
The Williams - Luxury 2-bedroom with On-Site Parking in Downtown Jacksonville
A small house with a porch, a bench, and a tree with white blossoms.

19. 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, (38 reviews)
"What a great location! We mostly sat by the river and enjoyed the scenery!"
United States
Christina B.
The price is AU$330
includes taxes & fees
14 Nov - 15 Nov
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to 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
"Wonderful location and very friendly, helpful staff. However it is the first hotel in 20 years of traveling that didn't have a hair dryer in each room."
Julia 1-night trip
Posted 1 hour ago
Stratford Inn

Find out more about Ashland

Ashland Cottages information

Number of reviews
861
Accommodation
126 Cottages
Lowest Price
AU$259
Highest Price
AU$581

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between AU$259 and AU$581 per night. These retreats offer a chance to soak up nature's beauty — at a price you can afford. This price was 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.
How many cottages are there in Ashland?
You'll find 126 cottages in Ashland. No matter if you're travelling with the kids or planning a weekend retreat with your buddies, Expedia can help you find the perfect place to reacquaint yourself with nature.
What is there to do in Ashland near my cottage?
You'll find loads of terrific things that'll fill up your itinerary in Ashland. Explore leading attractions like Oregon Shakespeare Festival, Mount Ashland Ski Area and Oregon Cabaret Theatre. Allen Elizabethan Theatre, Thomas Theatre and Angus Bowmer Theatre are other must-see's.

Explore a world of travel with Expedia