Search Cottages in Ashland

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Ashland cottages

Exterior
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )

Cottage in Ashland

Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
10.0 out of 10, Exceptional, (18)
"Wonderful location, well appointed place very quiet, beautifully located, and very special place on the farm"
United States
Greg M.
The price is AED 290
AED 656 total
includes taxes & fees
18 Dec - 19 Dec
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Exterior
The Ashland Cottage, walk to town

Cottage in Siskiyou-Hargadine Historic District

The Ashland Cottage, walk to town
10.0 out of 10, Exceptional, (211)
"The property was beautiful and just as described. We were rewarded with a kitty visit on the deck in the mornings while we drank our tea and coffee. Perfect distance from town, able to walk but not in all of the hubbub. "
United States
Jeanette S.
The price is AED 624
AED 1,048 total
includes taxes & fees
8 Jan - 9 January 2026
The Ashland Cottage, walk to town
Property grounds
Charming carriage house in Ashland near downtown

Cottage in Skidmore Academy Historic District

Charming carriage house in Ashland near downtown
10.0 out of 10, Exceptional, (6)
"Enjoyed our stay"
United States
Julie M.
Charming carriage house in Ashland near downtown
Fridge, microwave, coffee/tea maker, toaster
Courtside Cottage - WalkScore 93 - Dog Friendly

Cottage in Historic Railroad District

Courtside Cottage - WalkScore 93 - Dog Friendly
10.0 out of 10, Exceptional, (59)
"Great Location and Comfortable Unit."
United States
John V.
The price is AED 321
AED 751 total
includes taxes & fees
11 Dec - 12 Dec
Courtside Cottage - WalkScore 93 - Dog Friendly
Outdoor dining
Railroad District, steps to downtown, everything you need to enjoy Ashland!

Cottage in Historic Railroad District

Railroad District, steps to downtown, everything you need to enjoy Ashland!
2.0 star property
The price is AED 917
AED 1,989 total
includes taxes & fees
11 Dec - 12 Dec
Railroad District, steps to downtown, everything you need to enjoy Ashland!
Terrace/patio
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!

Cottage in Siskiyou-Hargadine Historic District

Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
10.0 out of 10, Exceptional, (5)
The price is AED 803
AED 1,375 total
includes taxes & fees
15 Dec - 16 Dec
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
Property grounds
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More

Cottage in Historic Railroad District

Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
9.6 out of 10, Exceptional, (19)
"We loved "
United States
Phyllis M.
The price is AED 889
AED 1,486 total
includes taxes & fees
11 Dec - 12 Dec
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
Glamp Cottage Trailer | Terrace/patio
Paschal Winery

Cottage in Talent

Paschal Winery
4.5 star property
9.6 out of 10, Exceptional, (14)
"Very nice and hassle free check in "
United States
Matthew
The price is AED 441
AED 797 total
includes taxes & fees
17 Dec - 18 Dec
Paschal Winery
Cottage (1 Bedroom) | Interior
On-site Winery & Tasting Room: Oregon Bungalow!

Cottage in Central Point

On-site Winery & Tasting Room: Oregon Bungalow!
3.0 star property
8.4 out of 10, Very Good, (5)
"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 AED 426
AED 809 total
includes taxes & fees
12 Dec - 13 Dec
On-site Winery & Tasting Room: Oregon Bungalow!
Exterior
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

Cottage in Central Point

Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
9.8 out of 10, Exceptional, (101)
"This was just what we needed as our halfway point of our trip. Area was quiet and close torestaurants. L9ved our stay here. It was a very hot day, but we were able to remain cool here."
United States
carol A.
The price is AED 360
AED 649 total
includes taxes & fees
21 Dec - 22 Dec
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Exterior
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville

Cottage in Central Point

Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
10.0 out of 10, Exceptional, (3)
"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 AED 496
AED 764 total
includes taxes & fees
8 Jan - 9 January 2026
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
Exterior
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville

Cottage in Jacksonville

Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
9.8 out of 10, Exceptional, (32)
"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 AED 441
AED 801 total
includes taxes & fees
11 Dec - 12 Dec
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Exterior
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

Cottage in City Center Medford

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
9.6 out of 10, Exceptional, (22)
"Great property everything we needed close to town perfect stay!"
United States
Chuck F.
The price is AED 420
AED 861 total
includes taxes & fees
14 Dec - 15 Dec
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
Terrace/patio
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.

Cottage in Central Point

Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
9.8 out of 10, Exceptional, (26)
"Great host, cute surroundings, lovely stay."
United States
Katie B.
The price is AED 459
AED 854 total
includes taxes & fees
18 Dec - 19 Dec
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Exterior
🌻 Charming Cottage On Peaceful 5 Acres in the Mountains

Cottage in Central Point

🌻 Charming Cottage On Peaceful 5 Acres in the Mountains
8.8 out of 10, Excellent, (9)
"This place was amazing. Took a little extra time to get to, but it was well worth it. Would definitely stay here again. Thanks again for all necessary accommodations as well. Definitely appreciated 🙏"
United States
Silent Tunez P.
The price is AED 459
AED 764 total
includes taxes & fees
11 Dec - 12 Dec
🌻 Charming Cottage On Peaceful 5 Acres in the Mountains
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

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 AED 404
AED 945 total
includes taxes & fees
18 Dec - 19 Dec
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
Microwave, coffee/tea maker, toaster, cookware/dishes/utensils
Rosewood Studio | Private Cottage Near Downtown

Cottage in Medford

Rosewood Studio | Private Cottage Near Downtown
8.0 out of 10, Very Good, (1)
"Location was as advertised."
United States
william L.
Rosewood Studio | Private Cottage Near Downtown
Exterior
Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT

Cottage in Jacksonville Historic District

Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT
10.0 out of 10, Exceptional, (45)
"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 AED 525
AED 1,096 total
includes taxes & fees
5 Jan - 6 January 2026
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

Cottage in Jacksonville Historic District

The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
10.0 out of 10, Exceptional, (1)
"The location was amazing: within walking distance of almost all the Jacksonville restaurants, stores, residential areas and the Britt Festival. The cottage was very cleaned and well-maintained. Ashley was very responsive and helpful in making all the arrangements for our party."
United States
Juliana S.
The price is AED 493
AED 1,319 total
includes taxes & fees
13 Dec - 14 Dec
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

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 AED 598
AED 1,519 total
includes taxes & fees
11 Dec - 12 Dec
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

Callahan's Mountain Lodge

Callahan's Mountain Lodge

10/10 Excellent
"This was an excellent experience!! This was my first time staying and my birthday and it was fantastic. The staff is no friendly and welcoming, the room clean, spacious and beautiful. The view is outstanding, morning breakfast buffet was a terrific start to the day.nawith great tasting foos "
David 2-night trip
Posted 2 days ago
Callahan's Mountain Lodge

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between AED 649 and AED 1,989 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 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.

Explore a world of travel with Expedia