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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Featured Cottages in Ashland

Railroad District, steps to downtown, everything you need to enjoy Ashland!
2 bedrooms, iron/ironing board, free WiFi, bed sheets

Railroad District, steps to downtown, everything you need to enjoy Ashland!

2.0 star property
The price is AU$971
includes taxes & fees
5 Oct - 6 Oct
Railroad District, steps to downtown, everything you need to enjoy Ashland!
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Exterior

Charming well appointed Cottage in Ashland ( 800 + sq. ft. )

10.0 out of 10, Exceptional, (18)
"This was indeed a charming property. We were intrigued by the rustic exterior, and were pleasantly surprised by the lovely, comfortable interior. It was a pleasure to be out of the downtown Ashland traffic and noise, yet it was so easy to get there when we wanted to. I would definitely stay here again."
The price is AU$274
includes taxes & fees
6 Oct - 7 Oct
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
The Ashland Cottage, walk to town
Exterior

The Ashland Cottage, walk to town

10.0 out of 10, Exceptional, (207)
"Great place for a couple. Nice house. Good location."
The price is AU$408
includes taxes & fees
5 Oct - 6 Oct
The Ashland Cottage, walk to town
Courtside Cottage - WalkScore 93 - Dog Friendly
Fridge, microwave, coffee/tea maker, toaster

Courtside Cottage - WalkScore 93 - Dog Friendly

10.0 out of 10, Exceptional, (54)
"Great location within walking distance to everything we wanted to do. Spotlessly clean, well equipped, comfortable bed…couldn’t ask for anything more!"
The price is AU$466
includes taxes & fees
5 Oct - 6 Oct
Courtside Cottage - WalkScore 93 - Dog Friendly
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
Terrace/patio

Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!

10.0 out of 10, Exceptional, (1)
"Great location, many personal touches and the host cares about comfort! Will stay again, thanks so much! "
The price is AU$574
includes taxes & fees
12 Oct - 13 Oct
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
Property grounds

Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More

10.0 out of 10, Exceptional, (17)
"This is a great spot to stay. "
The price is AU$621
includes taxes & fees
4 Nov - 5 Nov
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
Paschal Winery
Glamp Cottage Trailer | Terrace/patio

Paschal Winery

4.5 star property
9.6 out of 10, Exceptional, (12)
"Very nice and hassle free check in "
The price is AU$325
includes taxes & fees
4 Nov - 5 Nov
Paschal Winery
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Exterior

Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

9.8 out of 10, Exceptional, (99)
"This was just what we needed as our halfway point of our trip. Area was quiet and close torestaurants. L9ved our stay here. It was a very hot day, but we were able to remain cool here."
The price is AU$271
includes taxes & fees
5 Oct - 6 Oct
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
🌻 Charming Cottage On Peaceful 5 Acres in the Mountains
Exterior

🌻 Charming Cottage On Peaceful 5 Acres in the Mountains

9.0 out of 10, Wonderful, (8)
"This place was amazing. Took a little extra time to get to, but it was well worth it. Would definitely stay here again. Thanks again for all necessary accommodations as well. Definitely appreciated 🙏"
The price is AU$317
includes taxes & fees
2 Nov - 3 Nov
🌻 Charming Cottage On Peaceful 5 Acres in the Mountains
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
Exterior

Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville

10.0 out of 10, Exceptional, (1)
"Cute little place. Really pretty area and cute back yard with a lot of grass for our toddler to run around in. House lacked a few small details like a can opener but otherwise it had everything we needed. Soaps and shampoos, plenty of towels. Really nice property manager too!"
The price is AU$280
includes taxes & fees
11 Oct - 12 Oct
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
Downtown Mint
Exterior

Downtown Mint

9.8 out of 10, Exceptional, (38)
"We came to visit family and this place was perfect. We really enjoyed it."
The price is AU$319
includes taxes & fees
5 Oct - 6 Oct
Downtown Mint
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
Exterior

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

9.4 out of 10, Exceptional, (18)
"Loved this house. It was cozy and felt like someone’s home. "
The price is AU$368
includes taxes & fees
30 Oct - 31 Oct
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Exterior

Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville

9.6 out of 10, Exceptional, (28)
"We loved the animals and how peaceful it was there,The owner was very accommodating and nice. Highly recommend if I ever need to stay in the area again this would be my first pick "
The price is AU$331
includes taxes & fees
6 Oct - 7 Oct
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Terrace/patio

Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.

9.8 out of 10, Exceptional, (24)
"Lovely cottage. Extremely clean and well cared for. Convenient location to town.We have family in the area and we will definitely stay here again!"
The price is AU$357
includes taxes & fees
16 Oct - 17 Oct
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & savor sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville, this retreat blends charm & convenience
Exterior

Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & savor sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville, this retreat blends charm & convenience

The price is AU$390
includes taxes & fees
9 Oct - 10 Oct
Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & savor sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville, this retreat blends charm & convenience
Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT
Exterior

Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT

10.0 out of 10, Exceptional, (43)
"Outstanding "
The price is AU$540
includes taxes & fees
12 Oct - 13 Oct
Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
Exterior

The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville

The price is AU$551
includes taxes & fees
16 Oct - 17 Oct
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & savor sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville, this retreat blends charm & convenience
Exterior

Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & savor sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville, this retreat blends charm & convenience

The price is AU$718
includes taxes & fees
20 Oct - 21 Oct
Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & savor sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville, this retreat blends charm & convenience
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

Flagship Inn of Ashland

Flagship Inn of Ashland

10/10 Excellent
"Excellent, especially for the price. The bed was super comfy, and the room was well-appointed and nicely decorated. We will return and tell our friends about Flagship."
Delena 1-night trip
Posted 3 days ago
Flagship Inn of Ashland

Find out more about Ashland

Find out more about Ashland

Ashland Cottages information

Number of reviews
11
Accommodation
127 Cottages
Lowest Price
AU$325
Highest Price
AU$325

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between AU$325 and AU$325 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 127 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

Explore a world of travel with Expedia