A deer on a road with vegetation on the sides.

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
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 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 HK$1,317
HK$2,263 total
includes taxes & fees
22 Jun - 23 Jun
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)
"Enjoyed our stay"
United States
Julie M.
The price is HK$1,176
HK$2,089 total
includes taxes & fees
19 Jul - 20 Jul
Charming carriage house in Ashland near downtown
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, (9 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

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 HK$1,097
HK$2,132 total
includes taxes & fees
22 Jun - 23 Jun
Courtside Cottage - WalkScore 93 - Dog Friendly
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 HK$1,093
HK$3,319 total
includes taxes & fees
23 Jun - 24 Jun
Paschal Winery
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, (115 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 HK$768
HK$1,393 total
includes taxes & fees
1 Jul - 2 Jul
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Exterior

Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville

Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
Central Point
9.8 out of 10, Exceptional, (7 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 HK$1,023
HK$1,635 total
includes taxes & fees
30 Jun - 1 Jul
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 HK$940
HK$1,651 total
includes taxes & fees
1 Jul - 2 Jul
Rosewood Studio | Private Cottage Near Downtown
Exterior

Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (45 reviews)
"Loved the house, had a great stay!"
United States
Kara B.
The price is HK$712
HK$1,683 total
includes taxes & fees
23 Jun - 24 Jun
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 HK$1,277
HK$2,116 total
includes taxes & fees
30 Jun - 1 Jul
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
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 HK$1,136
HK$1,997 total
includes taxes & fees
8 Jul - 9 Jul
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
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 HK$1,672
HK$3,011 total
includes taxes & fees
9 Jul - 10 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, (80 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 HK$1,403
HK$3,175 total
includes taxes & fees
23 Jun - 24 Jun
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.
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 HK$1,161
HK$2,387 total
includes taxes & fees
22 Jun - 23 Jun
Historic Bradshaw House!
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 HK$1,319
HK$3,155 total
includes taxes & fees
30 Jun - 1 Jul
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
Exterior

Charming 1BR Cottage – Walk to Britt Gardens

Charming 1BR Cottage – Walk to Britt Gardens
Jacksonville
9.0 out of 10, Wonderful, (7 reviews)
"Location and interior was superb"
United States
Jonathan B.
The price is HK$1,153
HK$2,378 total
includes taxes & fees
22 Jun - 23 Jun
Charming 1BR Cottage – Walk to Britt Gardens
Exterior

Fireside Cottage in Downtown Jacksonville

Fireside Cottage in Downtown Jacksonville
Jacksonville Historic District
The price is HK$1,184
HK$2,123 total
includes taxes & fees
22 Jun - 23 Jun
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.
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

8/10 Good
"The area is beautiful."
deborah 1-night trip
Posted 1 hour ago
Callahan's Mountain Lodge

Find out more about Ashland

Ashland Cottages information

Number of reviews
724
Accommodation
127 Cottages
Lowest Price
HK$1,393
Highest Price
HK$3,319

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between HK$1,393 and HK$3,319 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 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?
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.

Explore a world of travel with Expedia