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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

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.
$211 nightly
The price is $214
May 5 - May 6
Total with taxes and fees
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, (221 reviews)
"Fun, functional, and super easy! Will stay here again "
United States
Andrew D.
$220 nightly
The price is $245
May 7 - May 8
Total with taxes and fees
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, (7 reviews)
"Great location, many personal touches and the host cares about comfort! Will stay again, thanks so much! "
United States
Krista M.
$336 nightly
The price is $374
May 5 - May 6
Total with taxes and fees
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, (10 reviews)
"Enjoyed our stay"
United States
Julie M.
$210 nightly
The price is $234
May 7 - May 8
Total with taxes and fees
Charming carriage house in Ashland near downtown
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)
"Courtside cottage is the perfect little place in the perfect location."
United States
Bradley
$214 nightly
The price is $238
May 5 - May 6
Total with taxes and fees
Courtside Cottage - WalkScore 93 - Dog Friendly
Exterior

Casa Amore, Ashland, Cozy Cottage in the Heart of Historic Ashland

Casa Amore, Ashland, Cozy Cottage in the Heart of Historic Ashland
Historic Railroad District
$252 nightly
The price is $281
May 5 - May 6
Total with taxes and fees
Casa Amore, Ashland, Cozy Cottage in the Heart of Historic Ashland
Room

The Garden Cottage at Second Street Cottages

The Garden Cottage at Second Street Cottages
Historic Railroad District
$283 nightly
The price is $316
May 11 - May 12
Total with taxes and fees
The Garden Cottage at Second Street Cottages
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
May 5 - May 6
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, (17 reviews)
"Incredible experience, fabulous wine, wish we had stayed longer to soak in the beauty of the experience. "
United States
Frankie
$282 nightly
The price is $286
May 28 - May 29
Total with taxes and fees
Paschal Winery
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.
$186 nightly
The price is $189
May 12 - May 13
Total with taxes and fees
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
Property grounds

Klamath River Ca Treehouse

Klamath River Ca Treehouse
Klamath River
$95 nightly
The price is $106
May 5 - May 6
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)
"Clean, cute, quiet, cozy…with all the comforts of home! Exactly what I was looking for!"
United States
Laura
$137 nightly
The price is $155
May 17 - May 18
Total with taxes and fees
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
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.
$228 nightly
The price is $231
May 5 - May 6
Total with taxes and fees
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Exterior

Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (44 reviews)
"Loved the house, had a great stay!"
United States
Kara B.
$201 nightly
The price is $226
May 6 - May 7
Total with taxes and fees
Downtown Mint
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.
$206 nightly
The price is $232
May 5 - May 6
Total with taxes and fees
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
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, (29 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.
$227 nightly
The price is $230
May 5 - May 6
Total with taxes and fees
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
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
9.6 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.
$329 nightly
The price is $353
May 11 - May 12
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.
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.
$171 nightly
The price is $195
May 10 - May 11
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, (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.
$295 nightly
The price is $314
May 5 - May 6
Total with taxes and fees
This cottage is a 2 bedroom(s), 2 bathrooms, located in Jacksonville, OR.
Exterior

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.
$364 nightly
The price is $403
May 18 - May 19
Total with taxes and fees
The Williams - luxe 2-bedroom cottage w/onsite parking 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

Prospero's Flagship Inn

Prospero's Flagship Inn

6/10 Okay
"I was checked in by a lovely woman who accidentally checked me in incorrectly. This caused me to get a 2 AM phone call saying that he was a no-show. Other than that, the location felt safe and comfortable and clean. Request for fruit or eggs at breakfast. Everything was carbohydrates and poor quality Nutrition food friendly staff will return. "
Shauna 3-night trip
Posted 11 hours ago
Prospero's Flagship Inn

Find out more about Ashland

Ashland Cottages information

Number of reviews
668
Accommodation
128 Cottages
Lowest Price
$106
Highest Price
$403

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between $106 and $403 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 9.8. 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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