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Our top choices for Ashland cottages

The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (222 reviews)
"Fun, functional, and super easy! Will stay here again "
United States
Andrew D.
The price is AED 551
AED 971 total
includes taxes & fees
20 May - 21 May
The Ashland Cottage, walk to town

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 AED 456
AED 861 total
includes taxes & fees
19 May - 20 May
Charming carriage house in Ashland near downtown

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, (7 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 AED 893
AED 1,491 total
includes taxes & fees
3 Jun - 4 Jun
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!

Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (62 reviews)
"Courtside cottage is the perfect little place in the perfect location."
United States
Bradley
The price is AED 546
AED 1,043 total
includes taxes & fees
18 May - 19 May
Courtside Cottage - WalkScore 93 - Dog Friendly

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)
"Great location"
United States
Kevin M.
Railroad District, steps to downtown, everything you need to enjoy Ashland!

Paschal Winery

Paschal Winery
4.5 star property
Talent
9.8 out of 10, Exceptional, (18 reviews)
"Incredible experience, fabulous wine, wish we had stayed longer to soak in the beauty of the experience. "
United States
Frankie
The price is AED 471
AED 1,029 total
includes taxes & fees
26 May - 27 May
Paschal Winery

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 AED 316
AED 674 total
includes taxes & fees
26 May - 27 May
On-site Winery & Tasting Room: Oregon Bungalow!

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 AED 511
AED 779 total
includes taxes & fees
10 Jun - 11 Jun
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville

Klamath River Ca Treehouse

Klamath River Ca Treehouse
Klamath River
The price is AED 275
AED 388 total
includes taxes & fees
15 May - 16 May
Klamath River Ca Treehouse

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 AED 522
AED 902 total
includes taxes & fees
18 May - 19 May
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville

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, (112 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 AED 291
AED 575 total
includes taxes & fees
26 May - 27 May
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

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.
Rosewood Studio | Private Cottage Near Downtown

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
City Center Medford
9.6 out of 10, Exceptional, (31 reviews)
"Great property everything we needed close to town perfect stay!"
United States
Chuck F.
The price is AED 426
AED 835 total
includes taxes & fees
19 May - 20 May
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

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, (30 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 AED 466
AED 861 total
includes taxes & fees
18 May - 19 May
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.

Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (44 reviews)
"Loved the house, had a great stay!"
United States
Kara B.
The price is AED 386
AED 847 total
includes taxes & fees
1 Jun - 2 Jun
Downtown Mint

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
9.6 out of 10, Exceptional, (4 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 AED 667
AED 1,266 total
includes taxes & fees
19 May - 20 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.

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 AED 602
AED 1,456 total
includes taxes & fees
18 May - 19 May
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville

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, (79 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 AED 398
AED 1,153 total
includes taxes & fees
18 May - 19 May
This cottage is a 2 bedroom(s), 2 bathrooms, located in Jacksonville, OR.

Charming 1BR Cottage – Walk to Britt Gardens

Charming 1BR Cottage – Walk to Britt Gardens
Jacksonville
9.0 out of 10, Wonderful, (7 reviews)
"Location and interior was superb"
United States
Jonathan B.
The price is AED 498
AED 1,071 total
includes taxes & fees
18 May - 19 May
Charming 1BR Cottage – Walk to Britt Gardens

Fireside Cottage in Downtown Jacksonville

Fireside Cottage in Downtown Jacksonville
Jacksonville Historic District
Fireside Cottage in Downtown Jacksonville
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

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between AED 388 and AED 1,491 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 121 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 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.