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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

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 ￥18,282
￥35,177 total
includes taxes & fees
Mar 13 - Mar 14
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Property grounds

The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (214 reviews)
"Perfect Stay!"
United States
Anonymous traveler
The price is ￥26,413
￥45,500 total
includes taxes & fees
Mar 16 - Mar 17
The Ashland Cottage, walk to town
Terrace/patio

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

Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
Historic Railroad District
10.0 out of 10, Exceptional, (5 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 ￥36,776
￥62,098 total
includes taxes & fees
Mar 25 - Mar 26
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
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, (9 reviews)
"Enjoyed our stay"
United States
Julie M.
Charming carriage house in Ashland near downtown
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
The price is ￥16,997
￥56,530 total
includes taxes & fees
Mar 25 - Mar 26
Railroad District, steps to downtown, everything you need to enjoy Ashland!
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, (19 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 ￥16,910
￥36,490 total
includes taxes & fees
Mar 16 - Mar 17
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
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 ￥18,234
￥38,234 total
includes taxes & fees
Mar 17 - Mar 18
Courtside Cottage - WalkScore 93 - Dog Friendly
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 ￥13,602
￥30,006 total
includes taxes & fees
Mar 30 - Mar 31
On-site Winery & Tasting Room: Oregon Bungalow!
Terrace/patio

Paschal Winery

Paschal Winery
4.5 star property
Talent
9.6 out of 10, Exceptional, (15 reviews)
"Great space and beautiful views. 10/10 experience. "
United States
Cody
The price is ￥17,533
￥41,642 total
includes taxes & fees
Mar 15 - Mar 16
Paschal Winery
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, (105 reviews)
"The stay was private and great "
United States
bradley s.
The price is ￥12,877
￥25,218 total
includes taxes & fees
Mar 18 - Mar 19
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, (4 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 ￥19,315
￥31,384 total
includes taxes & fees
Mar 19 - Mar 20
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)
"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 "
United States
Ryan K.
The price is ￥20,086
￥35,961 total
includes taxes & fees
Mar 16 - Mar 17
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, (25 reviews)
"Great property everything we needed close to town perfect stay!"
United States
Chuck F.
The price is ￥18,313
￥37,771 total
includes taxes & fees
Mar 19 - Mar 20
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
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 ￥22,558
￥37,614 total
includes taxes & fees
Mar 25 - Mar 26
Rosewood Studio | Private Cottage Near Downtown
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, (27 reviews)
"Great host, cute surroundings, lovely stay."
United States
Katie B.
The price is ￥19,871
￥36,789 total
includes taxes & fees
Mar 17 - Mar 18
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
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.
This cottage is a 2 bedroom(s), 2 bathrooms, located in Jacksonville, OR.
Exterior

Historic Bradshaw House!

Historic Bradshaw House!
Jacksonville
10.0 out of 10, Exceptional, (68 reviews)
"Great highly recommend"
United States
Linda J.
Historic Bradshaw House!
Exterior

Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (41 reviews)
"Loved the house, had a great stay!"
United States
Kara B.
Downtown Mint
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
9.0 out of 10, Wonderful, (2 reviews)
"The House was well setup and Very Clean. The check-in process and getting the Codes to the property was not explained in the Rental process and it was last minute. "
United States
George L.
The price is ￥17,662
￥40,762 total
includes taxes & fees
Mar 30 - Mar 31
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.
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 ￥27,184
￥54,457 total
includes taxes & fees
Mar 13 - Mar 14
TIGERS DEN - #1 BEST LOCATION, ROMANTIC, STUNNING, STEPS TO BRITT FESTIVAL
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

The Bard's Inn, BW Signature Collection by Best Western

The Bard's Inn, BW Signature Collection by Best Western

6/10 Okay
"Heater roared all night. Beds were adequate. Weirdly there was a mini fridge but no microwave. "kid" who checked us in def was not into his job, didn't really explain much of anything. The woman who was on duty in the morning was much more personable. Price ok for a three star motel."
Laura 1-night trip
Posted 15 hours ago
The Bard's Inn, BW Signature Collection by Best Western

Find out more about Ashland

Ashland Cottages information

Number of reviews
734
Accommodation
129 Cottages
Lowest Price
￥25,218
Highest Price
￥62,098

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between ￥25,218 and ￥62,098 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 129 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 kilometers 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 kilometers 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 vacation 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.

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