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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

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 €185
includes taxes & fees
23 Mar - 24 Mar
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Property grounds

Cottage in Siskiyou-Hargadine Historic District

The Ashland Cottage, walk to town
10.0 out of 10, Exceptional, (214 reviews)
"Perfect Stay!"
United States
Anonymous traveller
The price is €244
includes taxes & fees
3 Mar - 4 Mar
The Ashland Cottage, walk to town
Terrace/patio

Cottage in Historic Railroad District

Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
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.
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
Smart TV, books

Cottage in Historic Railroad District

Courtside Cottage - WalkScore 93 - Dog Friendly
10.0 out of 10, Exceptional, (62 reviews)
"Great place to stay very quaint very clean. Host is very gracious and communicated perfectly before the trip. Definitely would stay here again."
United States
Lantz B.
The price is €184
includes taxes & fees
3 Mar - 4 Mar
Courtside Cottage - WalkScore 93 - Dog Friendly
Property grounds

Cottage in Skidmore Academy Historic District

Charming carriage house in Ashland near downtown
9.8 out of 10, Exceptional, (9 reviews)
"Enjoyed our stay"
United States
Julie M.
Charming carriage house in Ashland near downtown
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)
"Close to everything; dog had plenty of room. Our go-to in Ashland; looking forward to staying again!"
United States
David A.
The price is €338
includes taxes & fees
3 Mar - 4 Mar
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
Smart TV, books

Cottage in Historic Railroad District

Railroad District, steps to downtown, everything you need to enjoy Ashland!
The price is €475
includes taxes & fees
3 Mar - 4 Mar
Railroad District, steps to downtown, everything you need to enjoy Ashland!
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 €161
includes taxes & fees
3 Mar - 4 Mar
On-site Winery & Tasting Room: Oregon Bungalow!
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 €180
includes taxes & fees
3 Mar - 4 Mar
Paschal Winery
Exterior

Cottage in Central Point

Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
9.8 out of 10, Exceptional, (105 reviews)
"The stay was private and great "
United States
bradley s.
The price is €145
includes taxes & fees
28 Mar - 29 Mar
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
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.
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
Exterior

Cottage in Central Point

Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
10.0 out of 10, Exceptional, (4 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 €168
includes taxes & fees
8 Mar - 9 Mar
Peaceful Countryside Stay with Scenic Views- 5 minutes 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 €191
includes taxes & fees
3 Mar - 4 Mar
Rosewood Studio | Private Cottage Near Downtown
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)
"We loved the animals and how peaceful it was there,The owner was very accommodating and nice. Highly recommend if I ever need to stay in the area again this would be my first pick "
United States
Ryan K.
The price is €186
includes taxes & fees
3 Mar - 4 Mar
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Exterior detail

Cottage in Jacksonville Historic District

This cottage is a 2 bedroom(s), 2 bathrooms, located in Jacksonville, OR.
9.8 out of 10, Exceptional, (78 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 €270
includes taxes & fees
3 Mar - 4 Mar
This cottage is a 2 bedroom(s), 2 bathrooms, located in Jacksonville, OR.
Exterior

Cottage in Jacksonville

Historic Bradshaw House!
10.0 out of 10, Exceptional, (68 reviews)
"Great highly recommend"
United States
Linda J.
The price is €263
includes taxes & fees
3 Mar - 4 Mar
Historic Bradshaw House!
Exterior

Cottage in Central Point

Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
9.8 out of 10, Exceptional, (27 reviews)
"Great host, cute surroundings, lovely stay."
United States
Katie B.
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Exterior

Cottage in Jacksonville Historic District

Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT
10.0 out of 10, Exceptional, (48 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 €255
includes taxes & fees
8 Mar - 9 Mar
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, & sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville. Charm, convenience & budget friendly.
9.0 out of 10, Wonderful, (2 reviews)
"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.
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 Jacksonville

Charming 1BR Cottage – Walk to Britt Gardens
9.0 out of 10, Wonderful, (7 reviews)
"Perfect downtown location and much nicer than the pictures show. "
United States
Lesha B.
The price is €259
includes taxes & fees
3 Mar - 4 Mar
Charming 1BR Cottage – Walk to Britt Gardens
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

Best Western Windsor Inn

Best Western Windsor Inn

10/10 Excellent
"Quiet comfortable rooms"
Robert 1-night trip
Posted 1 day ago
Best Western Windsor Inn

Find out more about Ashland

Ashland Cottages information

Number of reviews
686
Accommodation
129 Cottages
Lowest Price
€145
Highest Price
€475

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between €145 and €475 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 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.