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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Ashland cottages

A house with a wooden deck, a stone wall, and a wooden fence.

1. The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (241 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
The price is €263
includes taxes & fees
26 Oct - 27 Oct
The Ashland Cottage, walk to town
A modern living room with a grey sofa, a small table, and a basket on a white ottoman.

2. Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (77 reviews)
"Excellent stay. Very responsive host. Would come back"
United States
Scott N.
The price is €272
includes taxes & fees
5 Nov - 6 Nov
Courtside Cottage - WalkScore 93 - Dog Friendly
A residential house with a garage, a satellite dish, and a driveway.

3. Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown
Skidmore Academy Historic District
10.0 out of 10, Exceptional, (13 reviews)
"Lovely stay. "
United States
Cyndy K.
The price is €209
includes taxes & fees
27 Oct - 28 Oct
Charming carriage house in Ashland near downtown
An outdoor patio with a grill, dining table, chairs, and string lights.

4. Paschal Winery

Paschal Winery
4.5 star property
Talent
9.8 out of 10, Exceptional, (19 reviews)
"Stunning scenery, great wine and food. Friendly, helpful people on site and the hot tub is blissfully perfect ❤️"
United States
Christine
The price is €378
includes taxes & fees
18 Oct - 19 Oct
Paschal Winery
A house with a yellow front door, a blue door, and a garden with various flowers and plants.

5. Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (52 reviews)
"Good location and comfy beds!"
United States
Melissa L.
The price is €202
includes taxes & fees
2 Nov - 3 Nov
Downtown Mint
Exterior

6. 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, (129 reviews)
"Wonderful stay and will definitely do so again!!!"
United States
Kelly B.
The price is €163
includes taxes & fees
18 Oct - 19 Oct
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
A residential house with a front porch, a small garden with various plants and flowers, and a gravel driveway.

7. 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, (18 reviews)
"Everything was wonderful Will definitely stay again"
United States
Kellie P.
The price is €182
includes taxes & fees
23 Oct - 24 Oct
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
A single-story house with a gabled roof, surrounded by a variety of plants and shrubs.

8. HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
City Center Medford
9.6 out of 10, Exceptional, (48 reviews)
"Amazing location and the interior design was fabulous! Has everything you need and my dog had a great time too! All around awesome place, would highly recommend."
United States
Houda
The price is €244
includes taxes & fees
25 Oct - 26 Oct
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
A bedroom with a bed, a TV, a ladder, a mirror, a basket, and a door with a 'No Smoking' sign.

9. 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 €167
includes taxes & fees
19 Oct - 20 Oct
Rosewood Studio | Private Cottage Near Downtown
A blue house with a patio, a small table and chairs, and a hanging flower basket.

10. 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, (39 reviews)
"Lovely cottage with all the amenities in the countryside with beautiful views down a quiet lane. Perfect for our stay to visit Jacksonville and easy access to Medford airport."
United States
Vanessa C.
The price is €237
includes taxes & fees
21 Oct - 22 Oct
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
A bedroom with a fireplace, a bed with a headboard, a window, and a wall-mounted picture.

11. Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.

Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.
Jacksonville
9.6 out of 10, Exceptional, (4 reviews)
"Excellent location. The house was comfortable and had everything we needed."
United States
Christopher
The price is €270
includes taxes & fees
19 Oct - 20 Oct
Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.
A small, single-story house with a white picket fence, a purple front door, and a porch with white railings.

12. Historic Bradshaw House!

Historic Bradshaw House!
Jacksonville
10.0 out of 10, Exceptional, (70 reviews)
"We’ve stayed in Vrbo’s around the world and this is by far our favorite."
United States
Robert B.
The price is €265
includes taxes & fees
19 Oct - 20 Oct
Historic Bradshaw House!
A cabin with a stone exterior, a porch with a red door, and a sign reading "The Cottage."

13. Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
10.0 out of 10, Exceptional, (2 reviews)
"Thank you, this was a very clean, attractive property with everything needed. Maricio was the host & he was very attentive, kind & quick to respond . I highly recommend this property, it’s in a nice area & fun places to explore. Thanks for a great visit!"
United States
Jayne
The price is €199
includes taxes & fees
25 Oct - 26 Oct
Forest Cabin by Crater Lake & Klamath Falls
A two-story house with a front porch, a covered entryway, and a small front yard.

14. 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, (85 reviews)
"What an adorable cottage. It’s right in town but on a quiet street. It had every amenity that we needed. I would very highly recommend and would stay here again"
United States
Richard
The price is €272
includes taxes & fees
18 Oct - 19 Oct
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.
A two-story house with a sloped roof, multiple windows, and a well-maintained garden.

15. 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
9.0 out of 10, Wonderful, (7 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 €277
includes taxes & fees
25 Oct - 26 Oct
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.
A house with a stone pathway, white picket fence, and a small porch.

16. Charming 1BR Cottage – Walk to Britt Gardens

Charming 1BR Cottage – Walk to Britt Gardens
Jacksonville
9.2 out of 10, Wonderful, (9 reviews)
"Location and interior was superb"
United States
Jonathan B.
The price is €259
includes taxes & fees
1 Nov - 2 Nov
Charming 1BR Cottage – Walk to Britt Gardens
A residential property with a paved driveway leading to a front door, a wooden fence, and a small garden area.

17. The Williams - Luxury 2-bedroom with On-Site Parking in Downtown Jacksonville

The Williams - Luxury 2-bedroom with On-Site Parking in Downtown Jacksonville
Jacksonville Historic District
10.0 out of 10, Exceptional, (3 reviews)
"Lovely, comfortable stay, within easy walking distance to the Main Street of Jacksonville and all that has to offer. Very clean, beautifully decorated and comfortable. I highly recommend!"
United States
Janice C.
The price is €349
includes taxes & fees
19 Oct - 20 Oct
The Williams - Luxury 2-bedroom with On-Site Parking in Downtown Jacksonville
A small house with a porch, a bench, and a tree with white blossoms.

18. 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, (38 reviews)
"What a great location! We mostly sat by the river and enjoyed the scenery!"
United States
Christina B.
The price is €207
includes taxes & fees
9 Nov - 10 Nov
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
A cabin with a stone exterior, a porch with a red door, and a sign reading "The Cottage."

19. Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
Klamath Falls
9.0 out of 10, Wonderful, (6 reviews)
"The cabin is quiet and the kitchen is great for meals. We slept well and enjoyed the calm."
United States
Jo
The price is €206
includes taxes & fees
18 Oct - 19 Oct
Forest Cabin by Crater Lake & Klamath Falls
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

8/10 Good
"Breakfast was nearly empty and not great- staff did not care. Older property, it was reasonably clean but out of date."
Ernest 2-night trip
Posted 3 hours ago
Best Western Windsor Inn

Find out more about Ashland

Ashland Cottages information

Number of reviews
861
Accommodation
121 Cottages
Lowest Price
€163
Highest Price
€378

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between €163 and €378 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 121 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.