Search Ashland Cottage Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Ashland cottages

Exterior

Cottage in Ashland

Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
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 ￥17,906
￥34,295 total
includes taxes & fees
Feb 4 - Feb 5
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Property grounds

Cottage in Skidmore Academy Historic District

Charming carriage house in Ashland near downtown
10.0 out of 10, Exceptional, (7 reviews)
"Enjoyed our stay"
United States
Julie M.
The price is ￥16,407
￥32,787 total
includes taxes & fees
Feb 2 - Feb 3
Charming carriage house in Ashland near downtown
Smart TV, books

Cottage in Historic Railroad District

Courtside Cottage - WalkScore 93 - Dog Friendly
10.0 out of 10, Exceptional, (60 reviews)
"Very clean, great location. Well appointed . Loved it and would definitely come back. "
United States
Dawn
The price is ￥13,772
￥32,023 total
includes taxes & fees
Jan 28 - Jan 29
Courtside Cottage - WalkScore 93 - Dog Friendly
Property grounds

Cottage in Siskiyou-Hargadine Historic District

The Ashland Cottage, walk to town
10.0 out of 10, Exceptional, (212 reviews)
"Perfect Stay!"
United States
Anonymous traveler
The price is ￥26,002
￥44,445 total
includes taxes & fees
Jan 25 - Jan 26
The Ashland Cottage, walk to town
Smart TV, books

Cottage in Historic Railroad District

Railroad District, steps to downtown, everything you need to enjoy Ashland!
The price is ￥42,039
￥87,846 total
includes taxes & fees
Feb 5 - Feb 6
Railroad District, steps to downtown, everything you need to enjoy Ashland!
Terrace/patio

Cottage in Siskiyou-Hargadine Historic District

Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
10.0 out of 10, Exceptional, (5 reviews)
"Cozy, warm, clean, good kitchen facilities, 2 bathrooms great for a couple, parking."
United States
Jennie G.
The price is ￥34,052
￥58,280 total
includes taxes & fees
Feb 5 - Feb 6
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
Property grounds

Cottage in Historic Railroad District

Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
9.6 out of 10, Exceptional, (19 reviews)
"This is a great spot to stay. "
United States
Michelle G.
The price is ￥37,667
￥63,004 total
includes taxes & fees
Feb 5 - Feb 6
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
Terrace/patio

Cottage in Talent

Paschal Winery
4.5 star property
9.6 out of 10, Exceptional, (15 reviews)
"Great space and beautiful views. 10/10 experience. "
United States
Cody
The price is ￥18,506
￥33,576 total
includes taxes & fees
Feb 1 - Feb 2
Paschal Winery
Cottage (1 Bedroom) | Interior

Cottage in Central Point

On-site Winery & Tasting Room: Oregon Bungalow!
3.0 star property
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 ￥13,390
￥29,539 total
includes taxes & fees
Jan 25 - Jan 26
On-site Winery & Tasting Room: Oregon Bungalow!
Exterior

Cottage in Central Point

Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
9.8 out of 10, Exceptional, (104 reviews)
"The stay was private and great "
United States
bradley s.
The price is ￥12,384
￥24,631 total
includes taxes & fees
Jan 25 - Jan 26
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Exterior

Cottage in Central Point

Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
10.0 out of 10, Exceptional, (3 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 ￥18,918
￥31,055 total
includes taxes & fees
Feb 2 - Feb 3
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
Exterior

Cottage in Jacksonville

Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
9.8 out of 10, Exceptional, (32 reviews)
"Absolutely awesome place for a cute girls night! Loved all the animals. Just what we were looking for ."
United States
Natalie K.
The price is ￥18,684
￥33,504 total
includes taxes & fees
Jan 26 - Jan 27
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
1 bedroom, WiFi, bed sheets

Cottage in Medford

Rosewood Studio | Private Cottage Near Downtown
8.0 out of 10, Very Good, (1 review)
"Location was as advertised."
United States
william L.
The price is ￥19,007
￥32,882 total
includes taxes & fees
Jan 25 - Jan 26
Rosewood Studio | Private Cottage Near Downtown
Exterior

Cottage in City Center Medford

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
9.4 out of 10, Exceptional, (23 reviews)
"Great property everything we needed close to town perfect stay!"
United States
Chuck F.
The price is ￥17,937
￥36,470 total
includes taxes & fees
Jan 26 - Jan 27
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
Exterior

Cottage in Central Point

Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
9.8 out of 10, Exceptional, (26 reviews)
"Great host, cute surroundings, lovely stay."
United States
Katie B.
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Exterior

Cottage in Central Point

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.
8.0 out of 10, Very Good, (1 review)
"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 ￥17,127
￥38,948 total
includes taxes & fees
Jan 26 - Jan 27
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

Cottage in Central Point

🌻 Charming Cottage On Peaceful 5 Acres in the Mountains
8.8 out of 10, Excellent, (9 reviews)
"We LOVED the location and the charm of this home. However, there were no sheets or bedding for the pull out bed and only 2 towels for 3 people to stay. "
United States
Alyssa K.
The price is ￥21,798
￥34,611 total
includes taxes & fees
Jan 26 - Jan 27
🌻 Charming Cottage On Peaceful 5 Acres in the Mountains
Exterior

Cottage in Jacksonville Historic District

The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful place and great location"
United States
darren t.
The price is ￥22,281
￥56,966 total
includes taxes & fees
Jan 26 - Jan 27
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
Exterior

Cottage in Jacksonville Historic District

Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT
10.0 out of 10, Exceptional, (46 reviews)
"This place was awesome. Perfect location for walking to restaurants and Britt. The whole place was very clean. Looking forward to staying again"
United States
Ellen H.
The price is ￥22,265
￥47,487 total
includes taxes & fees
Feb 5 - Feb 6
Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT
Exterior

Cottage in Central Point

Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & savor sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville, this retreat blends charm & convenience
The price is ￥26,033
￥65,288 total
includes taxes & fees
Jan 26 - Jan 27
Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & savor sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville, this retreat blends charm & convenience
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashland Hotel Reviews

Ashland Springs Hotel

Ashland Springs Hotel

10/10 Excellent
"Everything was nice. "
Cindy 1-night trip
Posted 18 hours ago
Ashland Springs Hotel

Find out more about Ashland

Ashland Cottages information

Number of reviews
549
Accommodation
129 Cottages
Lowest Price
￥24,631
Highest Price
￥87,846

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between ￥24,631 and ￥87,846 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 9.6. 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.

Explore a world of travel with Expedia