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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 June - 14 June
In three months
10 July - 12 July
In four months
7 Aug - 9 Aug

Our top choices for Ashland cottages

Property grounds

The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (220 reviews)
"Fun, functional, and super easy! Will stay here again "
United States
Andrew D.
The price is AU$327
includes taxes & fees
19 Apr - 20 Apr
The Ashland Cottage, walk to town
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 AU$311
includes taxes & fees
23 Apr - 24 Apr
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Smart TV, books

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

Railroad District, steps to downtown, everything you need to enjoy Ashland!
Historic Railroad District
10.0 out of 10, Exceptional, (2 reviews)
"So close to down town , shops , coffee and restaurants! Enjoyed Noble Coffee, great find! Your location was quiet and set up just right for our visit! We’ll visit again! "
United States
Carla H.
The price is AU$592
includes taxes & fees
20 Apr - 21 Apr
Railroad District, steps to downtown, everything you need to enjoy Ashland!
Terrace/patio

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

Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (6 reviews)
"Great location, many personal touches and the host cares about comfort! Will stay again, thanks so much! "
United States
Krista M.
The price is AU$517
includes taxes & fees
19 Apr - 20 Apr
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
Smart TV, books

Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (62 reviews)
"Great place to stay very quaint very clean. Host is very gracious and communicated perfectly before the trip. Definitely would stay here again."
United States
Lantz B.
The price is AU$359
includes taxes & fees
21 Apr - 22 Apr
Courtside Cottage - WalkScore 93 - Dog Friendly
Property grounds

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

Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
Historic Railroad District
9.6 out of 10, Exceptional, (20 reviews)
"Close to everything; dog had plenty of room. Our go-to in Ashland; looking forward to staying again!"
United States
David A.
The price is AU$423
includes taxes & fees
20 Apr - 21 Apr
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
Property grounds

Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown
Skidmore Academy Historic District
9.8 out of 10, Exceptional, (10 reviews)
"Enjoyed our stay"
United States
Julie M.
The price is AU$356
includes taxes & fees
3 May - 4 May
Charming carriage house in Ashland near downtown
Cottage (1 Bedroom) | Interior

On-site Winery & Tasting Room: Oregon Bungalow!

On-site Winery & Tasting Room: Oregon Bungalow!
3.0 star property
Central Point
8.4 out of 10, Very good, (5 reviews)
"Loved our stay at the Bungalow. The owners were so welcoming, helpful and friendly. The bungalow was very clean and had well equipped. It wa a great location for everything we wanted to do. The bungalow was even nicer than the pictures. We would definitely recommend this stay! "
United States
Deborah
The price is AU$256
includes taxes & fees
18 May - 19 May
On-site Winery & Tasting Room: Oregon Bungalow!
Dream Cottage 1 | Terrace/patio

Paschal Winery

Paschal Winery
4.5 star property
Talent
9.8 out of 10, Exceptional, (16 reviews)
"The cottage was really nice. It was clean and nicely decorated. It had so many amenities including a well stocked kitchen , comfortable beds and a great hot tub with an amazing view. The management was friendly and allowed us to check in early which was great."
United States
Jennifer
The price is AU$358
includes taxes & fees
30 Apr - 1 May
Paschal Winery
Property grounds

Klamath River Ca Treehouse

Klamath River Ca Treehouse
Klamath River
The price is AU$150
includes taxes & fees
1 May - 2 May
Klamath River Ca Treehouse
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, (111 reviews)
"The stay was private and great "
United States
bradley s.
The price is AU$218
includes taxes & fees
22 Apr - 23 Apr
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
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, (5 reviews)
"Booking and check-in were very smooth. The property is as advertised and more! Peaceful, beautiful, comfortable and convenient to Jacksonville and nearby areas. Will look forward to staying again. "
United States
Ruth P.
The price is AU$270
includes taxes & fees
2 May - 3 May
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
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, (32 reviews)
"Clean sweet comfortable and well priced"
United States
Linda C.
The price is AU$312
includes taxes & fees
20 Apr - 21 Apr
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Exterior

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
City Center Medford
9.6 out of 10, Exceptional, (26 reviews)
"Great property everything we needed close to town perfect stay!"
United States
Chuck F.
The price is AU$327
includes taxes & fees
20 Apr - 21 Apr
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
Exterior

Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (43 reviews)
"Loved the house, had a great stay!"
United States
Kara B.
The price is AU$324
includes taxes & fees
19 Apr - 20 Apr
Downtown Mint
Exterior

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

Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Central Point
9.8 out of 10, Exceptional, (28 reviews)
"Location was quiet and private, perfect for a break from busy schedule. Cottage was charming with especially comfortable couch and bed. Great surroundings for walking the dog. "
United States
T L.
The price is AU$322
includes taxes & fees
21 Apr - 22 Apr
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
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 AU$258
includes taxes & fees
26 Apr - 27 Apr
Rosewood Studio | Private Cottage Near Downtown
Exterior detail

This cottage is a 2 bedroom(s), 2 bathrooms, located in Jacksonville, OR.

This cottage is a 2 bedroom(s), 2 bathrooms, located in Jacksonville, OR.
Jacksonville Historic District
9.8 out of 10, Exceptional, (78 reviews)
"The host was very helpful and responsive to questions. The location was wonderful, and the property was clean and warm. A very nice place to stay!"
United States
Sarah F.
The price is AU$450
includes taxes & fees
29 Apr - 30 Apr
This cottage is a 2 bedroom(s), 2 bathrooms, located in Jacksonville, OR.
Exterior

TIGERS DEN - #1 BEST LOCATION, ROMANTIC, STUNNING, STEPS TO BRITT FESTIVAL

TIGERS DEN - #1 BEST LOCATION, ROMANTIC, STUNNING, STEPS TO BRITT FESTIVAL
Jacksonville Historic District
10.0 out of 10, Exceptional, (37 reviews)
"Super great space! Cute, cozy, and easy walk to downtown and the Britt. Perfect girls getaway!"
United States
Brooke C.
The price is AU$464
includes taxes & fees
1 May - 2 May
TIGERS DEN - #1 BEST LOCATION, ROMANTIC, STUNNING, STEPS TO 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
9.4 out of 10, Exceptional, (3 reviews)
"Very relaxing, gorgeous views! Home was very clean and well stocked. We had everything we needed to make dinner and spend time with family at this great little house. Soft linens, comfy beds, good towels. Clearly the owners take pride in the home and hosting. There was another visitor staying in the RV at the time and it was never an issue. The land is big enough that we each had our own space. The whole area is fenced making it safe and easy. Would stay here again for sure. "
United States
gianna b.
The price is AU$359
includes taxes & fees
4 May - 5 May
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.
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

Stratford Inn

Stratford Inn

6/10 Okay
"It was a fine stay but not that great. The heating/cooling unit did not work properly - based on other reviews that seems to be a common issue. The breakfast wasn’t great but as expected. Staff was super friendly."
Emily 1-night trip
Posted 2 hours ago
Stratford Inn

Find out more about Ashland

Ashland Cottages information

Number of reviews
718
Accommodation
128 Cottages
Lowest Price
AU$150
Highest Price
AU$592

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between AU$150 and AU$592 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 128 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.

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