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In two months
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In three months
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In four months
Aug 7 - Aug 9

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.
$205 nightly
The price is $229
Apr 19 - Apr 20
Total with taxes and fees
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.
$216 nightly
The price is $219
Apr 23 - Apr 24
Total with taxes and fees
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.
$385 nightly
The price is $429
Apr 19 - Apr 20
Total with taxes and fees
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.
$334 nightly
The price is $372
Apr 19 - Apr 20
Total with taxes and fees
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.
$217 nightly
The price is $242
Apr 21 - Apr 22
Total with taxes and fees
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.
$245 nightly
The price is $273
Apr 20 - Apr 21
Total with taxes and fees
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.
$216 nightly
The price is $240
May 7 - May 8
Total with taxes and fees
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
$181 nightly
The price is $184
Apr 21 - Apr 22
Total with taxes and fees
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
$257 nightly
The price is $261
Apr 19 - Apr 20
Total with taxes and fees
Paschal Winery
Property grounds

Klamath River Ca Treehouse

Klamath River Ca Treehouse
Klamath River
$95 nightly
The price is $106
Apr 19 - Apr 20
Total with taxes and fees
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.
$137 nightly
The price is $154
Apr 22 - Apr 23
Total with taxes and fees
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.
$188 nightly
The price is $191
Apr 26 - Apr 27
Total with taxes and fees
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.
$219 nightly
The price is $222
Apr 20 - Apr 21
Total with taxes and fees
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.
$201 nightly
The price is $226
Apr 19 - Apr 20
Total with taxes and fees
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.
$201 nightly
The price is $226
Apr 19 - Apr 20
Total with taxes and fees
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.
$222 nightly
The price is $225
Apr 21 - Apr 22
Total with taxes and fees
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.
$160 nightly
The price is $183
Apr 26 - Apr 27
Total with taxes and fees
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.
$303 nightly
The price is $323
May 4 - May 5
Total with taxes and fees
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.
$308 nightly
The price is $340
Apr 19 - Apr 20
Total with taxes and fees
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.
$239 nightly
The price is $257
May 4 - May 5
Total with taxes and fees
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

Callahan's Mountain Lodge

Callahan's Mountain Lodge

8/10 Good
"Convenient right off the Freeway at the top of Siskiyou pass. 4000’ elevation with some deer running around. Nice area"
Steven 1-night trip
Posted 5 hours ago
Callahan's Mountain Lodge

Find out more about Ashland

Ashland Cottages information

Number of reviews
718
Accommodation
128 Cottages
Lowest Price
$106
Highest Price
$429

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between $106 and $429 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 128 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 3 miles 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 0.5 miles 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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