A deer on a road with vegetation on the sides.

Book a Ashland Cottage

  • 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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Ashland cottages

Exterior

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 NZ$415
includes taxes & fees
4 Aug - 5 Aug
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Property grounds

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 NZ$435
includes taxes & fees
25 Aug - 26 Aug
Charming carriage house in Ashland near downtown
Property grounds

The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (231 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
The price is NZ$514
includes taxes & fees
24 Aug - 25 Aug
The Ashland Cottage, walk to town
Smart TV, books

Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (67 reviews)
"Spacious, clean studio to explore Ashland!"
United States
Suzanne
The price is NZ$563
includes taxes & fees
4 Aug - 5 Aug
Courtside Cottage - WalkScore 93 - Dog Friendly
Dream Cottage 1 | Terrace/patio

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 NZ$731
includes taxes & fees
30 July - 31 July
Paschal Winery
1 bedroom, WiFi, bed sheets

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 NZ$360
includes taxes & fees
29 July - 30 July
Rosewood Studio | Private Cottage Near Downtown
Exterior

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, (15 reviews)
"Everything was wonderful Will definitely stay again"
United States
Kellie P.
The price is NZ$367
includes taxes & fees
7 Aug - 8 Aug
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
Exterior

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, (123 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 NZ$278
includes taxes & fees
3 Aug - 4 Aug
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Exterior

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
City Center Medford
9.6 out of 10, Exceptional, (39 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 NZ$424
includes taxes & fees
3 Aug - 4 Aug
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
Exterior

Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (48 reviews)
"Good location and comfy beds!"
United States
Melissa L.
The price is NZ$496
includes taxes & fees
8 Aug - 9 Aug
Downtown Mint
Exterior

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, (1 review)
"Cyd was an amazing host and very accommodating. This is a quaint little cottage with everything you need to cook a meal. I love that it’s within walking distance of downtown Jacksonville and the Britt."
United States
Jessica P.
The price is NZ$315
includes taxes & fees
29 July - 30 July
Charming Jacksonville Studio with AC • Easy Walk to Town & Britt Festival
Exterior

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 NZ$497
includes taxes & fees
29 July - 30 July
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.
Interior

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 NZ$527
includes taxes & fees
29 July - 30 July
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.
Exterior

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, (33 reviews)
"Great host, cute surroundings, lovely stay."
United States
Katie B.
The price is NZ$471
includes taxes & fees
18 Aug - 19 Aug
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Exterior

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 NZ$429
includes taxes & fees
18 Aug - 19 Aug
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Exterior

Historic Bradshaw House!

Historic Bradshaw House!
Jacksonville
10.0 out of 10, Exceptional, (70 reviews)
"Creatively decorated and cozy. Bed a bit lumpy but overall a lovely little cottage perfectly located next to Main Street."
United States
Nancy L.
The price is NZ$501
includes taxes & fees
29 July - 30 July
Historic Bradshaw House!
Exterior

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, (83 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 NZ$651
includes taxes & fees
29 July - 30 July
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.
Exterior

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 NZ$699
includes taxes & fees
10 Aug - 11 Aug
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
Exterior

Fireside Cottage in Downtown Jacksonville

Fireside Cottage in Downtown Jacksonville
Jacksonville Historic District
The price is NZ$424
includes taxes & fees
3 Aug - 4 Aug
Fireside Cottage in Downtown Jacksonville
House (0 Bedroom) | Interior

Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
The price is NZ$405
includes taxes & fees
9 Aug - 10 Aug
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.
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

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

10/10 Excellent
"24 hr indoor pool and hot tub Close to freeway Waffles bacon or snausages & eggs type breakfast. Chill staff who get you in, or on your way, with the quickness. Asked if I could check in a half hour early on a hot day and since there was a room ready, they were able to accommodate."
Cameron 2-night trip
Posted 2 hours ago
Comfort Inn & Suites Ashland

Find out more about Ashland

Ashland Cottages information

Number of reviews
803
Accommodation
127 Cottages
Lowest Price
NZ$278
Highest Price
NZ$731

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between NZ$278 and NZ$731 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.
How many cottages are there in Ashland?
Pack your suitcase and pick from 127 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.
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.

Explore a world of travel with Expedia