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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

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, (225 reviews)
"Great spot, close to town, cozy and comfortable!"
United States
Carey C.
The price is £219
includes taxes & fees
13 Jul - 14 Jul
The Ashland Cottage, walk to town
Property grounds

Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown
Skidmore Academy Historic District
10.0 out of 10, Exceptional, (11 reviews)
"Lovely stay. "
United States
Cyndy K.
The price is £186
includes taxes & fees
19 Jul - 20 Jul
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, (64 reviews)
"Spacious, clean studio to explore Ashland!"
United States
Suzanne
The price is £248
includes taxes & fees
27 Jul - 28 Jul
Courtside Cottage - WalkScore 93 - Dog Friendly
House (0 Bedroom) | Interior

Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
The price is £166
includes taxes & fees
26 Jul - 27 Jul
Forest Cabin by Crater Lake & Klamath Falls
Dream Cottage 1 | Terrace/patio

Paschal Winery

Paschal Winery
4.5 star property
Talent
9.8 out of 10, Exceptional, (19 reviews)
"Incredible experience, fabulous wine, wish we had stayed longer to soak in the beauty of the experience. "
United States
Frankie
The price is £306
includes taxes & fees
5 Jul - 6 Jul
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, (11 reviews)
"Everything was wonderful Will definitely stay again"
United States
Kellie P.
The price is £153
includes taxes & fees
14 Jul - 15 Jul
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
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, (116 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 £137
includes taxes & fees
6 Jul - 7 Jul
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Exterior

Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
Klamath Falls
9.2 out of 10, Wonderful, (5 reviews)
"The property is perfect for two. Everything was very clean, organized and comfortable. "
United States
Jennifer J.
Forest Cabin by Crater Lake & Klamath Falls
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 £150
includes taxes & fees
5 Jul - 6 Jul
Rosewood Studio | Private Cottage Near Downtown
Exterior

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
City Center Medford
9.6 out of 10, Exceptional, (36 reviews)
"Amazing location and the interior design was fabulous! Has everything you need and my dog had a great time too! All around awesome place, would highly recommend."
United States
Houda
The price is £192
includes taxes & fees
9 Jul - 10 Jul
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
9.6 out of 10, Exceptional, (32 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 £178
includes taxes & fees
7 Jul - 8 Jul
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Exterior

Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (48 reviews)
"This is a great place to stay in Medford. The house is in a quiet neighborhood but close to restaurants and shopping. The house was immaculate and very comfortable. We had everything we needed for our stay. I would highly recommend this house if you are going to Medford "
United States
David F.
The price is £186
includes taxes & fees
6 Jul - 7 Jul
Downtown Mint
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, (34 reviews)
"Knocked our socks off. Beautiful place, with animals in a green space and riverside hangouts on the Applegate. Lodgings next to the road, but that’s quiet at night and the river side is where you hang out. The host has built something special, and she’s on it all the time. She’s also more than tidy, so less is more, which some of us love. Don’t miss the tiny towns on the west, Applegate, Provolt, and Williams. They’re tiny but friendly."
United States
Edmond
The price is £198
includes taxes & fees
21 Jul - 22 Jul
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Property grounds

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 £288
includes taxes & fees
14 Jul - 15 Jul
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

Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.

Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.
Jacksonville Historic District
9.8 out of 10, Exceptional, (82 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 £306
includes taxes & fees
28 Jul - 29 Jul
Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.
Interior

Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.

Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.
Jacksonville
10.0 out of 10, Exceptional, (1 review)
"Excellent location. The house was comfortable and had everything we needed."
United States
Christopher
The price is £245
includes taxes & fees
28 Jul - 29 Jul
Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.
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.
The price is £310
includes taxes & fees
7 Jul - 8 Jul
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
Exterior

Historic Bradshaw House!

Historic Bradshaw House!
Jacksonville
10.0 out of 10, Exceptional, (69 reviews)
"Creatively decorated and cozy. Bed a bit lumpy but overall a lovely little cottage perfectly located next to Main Street."
United States
Nancy L.
The price is £264
includes taxes & fees
21 Jul - 22 Jul
Historic Bradshaw House!
Exterior

Charming Jacksonville Studio with AC • Easy Walk to Town & Britt Festival

Charming Jacksonville Studio with AC • Easy Walk to Town & Britt Festival
Jacksonville, OR
The price is £141
includes taxes & fees
6 Jul - 7 Jul
Charming Jacksonville Studio with AC • Easy Walk to Town & Britt Festival
Exterior

Fireside Cottage in Downtown Jacksonville

Fireside Cottage in Downtown Jacksonville
Jacksonville Historic District
The price is £219
includes taxes & fees
2 Jul - 3 Jul
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

Callahan's Mountain Lodge

Callahan's Mountain Lodge

8/10 Good
"It was a nice place to relax on a way from long trip. Room is very cozy with little imperfections, almost like home. The restaurant had a great options for dinner, breakfast however felt little bit too relaxed. It was ok, but having bacon would be nice."
Oleg 1-night trip
Posted 2 hours ago
Callahan's Mountain Lodge

Find out more about Ashland

Ashland Cottages information

Number of reviews
755
Accommodation
127 Cottages
Lowest Price
£137
Highest Price
£310

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between £137 and £310 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 offers multiple cottages with a total average guest review rating of 9.8. Oak Street Cottages is a good option if you prefer nature and a relaxing pace. Visitors staying at this 3-star stay will have use of a barbecue grill and a fireplace. The Retreat At Oak Knoll ~ Pet Friendly is another popular choice. This 4-star cottage has a yard and a garden.
How many cottages are there in Ashland?
Pack your suitcase and pick from 127 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?
Settle in at Oak Street Cottages, a 3-star cottage just a quick drive from downtown. Conveniences here include WiFi and a fireplace. Another family-friendly pick where you can swap the urban jungle for nature is The Retreat At Oak Knoll ~ Pet Friendly. A fireplace and a barbecue grill help make this 4-star cottage a hit with guests. Ashland boasts an array of family-friendly attractions to visit that'll entertain the kids. North Mountain Park and Emigrant Lake promise a fun-filled day for visitors of all ages.
Are there any 5-star cottages in Ashland?
Ashland does not have any 5-star cottages — but you and the crew can still have a stylish stay here! Why not have a look at C' Street Station - Short Walk To Osf? Located about 0.5 mi from the downtown area, this 4-star retreat comes with a fireplace and free WiFi. The Retreat At Oak Knoll ~ Pet Friendly is another terrific 4-star pick just 3 mi from central Ashland. It offers a stress-free vibe close to nature on top of conveniences like a living room and a garden.
Why book your cottage in Ashland with Expedia?
Expedia has some superb cottages in Ashland, so get set for a memorable holiday 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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