Search Cottages in Ashland

  • 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
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Ashland cottages

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, (6 reviews)
"Enjoyed our stay"
United States
Julie M.
The price is €180
includes taxes & fees
16 Jan - 17 Jan
Charming carriage house in Ashland near downtown
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.
The price is €213
includes taxes & fees
29 Jan - 30 Jan
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, (212 reviews)
"Perfect Stay!"
United States
Anonymous traveller
The price is €251
includes taxes & fees
16 Jan - 17 Jan
The Ashland Cottage, walk to town
Smart TV, books

Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
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 €208
includes taxes & fees
27 Jan - 28 Jan
Courtside Cottage - WalkScore 93 - Dog Friendly
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, (5 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 €319
includes taxes & fees
16 Jan - 17 Jan
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
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!
2.0 star property
Historic Railroad District
The price is €547
includes taxes & fees
16 Jan - 17 Jan
Railroad District, steps to downtown, everything you need to enjoy Ashland!
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, (19 reviews)
"This is a great spot to stay. "
United States
Michelle G.
The price is €357
includes taxes & fees
1 Feb - 2 Feb
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
Terrace/patio

Paschal Winery

Paschal Winery
4.5 star property
Talent
9.6 out of 10, Exceptional, (15 reviews)
"Great space and beautiful views. 10/10 experience. "
United States
Cody
The price is €193
includes taxes & fees
18 Jan - 19 Jan
Paschal Winery
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
The price is €163
includes taxes & fees
16 Jan - 17 Jan
On-site Winery & Tasting Room: Oregon Bungalow!
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)
"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 €191
includes taxes & fees
15 Feb - 16 Feb
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
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, (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 €173
includes taxes & fees
22 Jan - 23 Jan
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
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 €181
includes taxes & fees
18 Jan - 19 Jan
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, (22 reviews)
"Great property everything we needed close to town perfect stay!"
United States
Chuck F.
The price is €205
includes taxes & fees
18 Jan - 19 Jan
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, (26 reviews)
"Great host, cute surroundings, lovely stay."
United States
Katie B.
The price is €201
includes taxes & fees
17 Jan - 18 Jan
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
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 €231
includes taxes & fees
28 Jan - 29 Jan
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 Cottage On Peaceful 5 Acres in the Mountains

🌻 Charming Cottage On Peaceful 5 Acres in the Mountains
Central Point
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 €197
includes taxes & fees
16 Jan - 17 Jan
🌻 Charming Cottage On Peaceful 5 Acres in the Mountains
Exterior

Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT

Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT
Jacksonville Historic District
10.0 out of 10, Exceptional, (45 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 €265
includes taxes & fees
25 Jan - 26 Jan
Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT
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 Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
Exterior

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

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
Central Point
The price is €354
includes taxes & fees
19 Jan - 20 Jan
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

Flagship Inn of Ashland

Flagship Inn of Ashland

10/10 Excellent
"Clean and staff had great attitude with friendly service. "
Jonathan 1-night trip
Posted 1 day ago
Flagship Inn of Ashland

Find out more about Ashland

Ashland Cottages information

Number of reviews
443
Accommodation
129 Cottages
Lowest Price
€163
Highest Price
€547

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between €163 and €547 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 kilometres 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 kilometres 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 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.