Best Cottages in Ashland in 2026

Q: Are there any family-friendly cottages in Ashland?

Settle in at Oak Street Cottages , a 3-star cottage just a quick drive from downtown. Conveniences here include WiFi and a fireplace. Another family-friendly pick where you can swap the urban jungle for nature is The Retreat At Oak Knoll ~ Pet Friendly . A fireplace and a barbecue grill help make this 4-star cottage a hit with guests. Ashland boasts an array of family-friendly attractions to visit that'll entertain the kids. North Mountain Park and Emigrant Lake promise a fun-filled day for visitors of all ages.

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Our top choices for Ashland cottages

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

Ashland

Greg M.

includes taxes & fees

22 Aug - 23 Aug

2. Charming carriage house in Ashland near downtown

Skidmore Academy Historic District

Cyndy K.

includes taxes & fees

25 Aug - 26 Aug

3. The Ashland Cottage, walk to town

Siskiyou-Hargadine Historic District

Julie S.

includes taxes & fees

24 Aug - 25 Aug

4. Courtside Cottage - WalkScore 93 - Dog Friendly

Historic Railroad District

Suzanne

includes taxes & fees

25 Aug - 26 Aug

5. Paschal Winery

Talent

Christine

includes taxes & fees

3 Sept - 4 Sept

6. Downtown Mint

Medford

Melissa L.

includes taxes & fees

17 Aug - 18 Aug

7. Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

Central Point

Chris A.

includes taxes & fees

18 Aug - 19 Aug

8. Rosewood Studio | Private Cottage Near Downtown

Medford

william L.

includes taxes & fees

16 Aug - 17 Aug

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Top Ashland Hotel Reviews

Ashland Hills Hotel & Suites

10/10 Excellent

"As sprawling Ashland Hills is well-designed to host large events, it isn't the place one would go for intimacy or charm, or walking access to downtown. But it's a perfect place to go if you like spacious, clean rooms and comfortable beds (with soft pillows!), and easy access to parking, pool, tennis courts, a large, fenced dog area for my Golden Retriever - and beautiful views if you ask in advance. Too tired to venture out, I was somewhat surprised to be able to order a dinner with perfectly cooked wild salmon! (I'm guessing that a real espresso bar would be a popular addition, but there are plenty within a 5 minute drive.)"

Comfort Inn & Suites Ashland

8/10 Good

"The room was very clean, roomy. Bed was comfy, air conditioner worked well. Breakfast had lots of options (although I think the eggs were reconstituted powdered eggs) Staff were pleasant, the person who checked us in was trying to do too many things at once and not succeeding, but we got checked in ok."

Callahan's Mountain Lodge

10/10 Excellent

"Callahans is a southern Oregon institution. I have been going to this resort in the mountains for over a half century. My wife and I spent the night, had dinner and breakfast: we watched the Perseid meteor shower from the top of nearby Mt Ashland. From cocktails on the wonderful expansive decks to a tasty scallop dinner choice, it was a wonderful evening….. The room was standard but was expansive and tastefully decorated with mountain themes. The staff truly wanted us to have a great time. Consider this resort for a mountain get away……"

Timbers INN and Suites

8/10 Good

"Great service from Gurpik (not sure I've spelled his name right...), who moved me to a ground-floor room so I could secure my bike overnight. The pool—small, but refreshing—was very nice after a long day's drive in hot summer temperatures. The pizza place right next door is also a nice "amenity," good pizza and beer. Had a good night's sleep after the family right over my room upstairs quieted down, lot of noise from running but did not go on too late. All in all, very good value for a place tp stop over in Ashland."

Find out more about Ashland

Ashland Cottages information

Number of reviews	753
Accommodation	126 Cottages
Lowest Price	£122
Highest Price	£311

Frequently asked questions

How much do cottages in Ashland cost?

Cottages in Ashland range between £122 and £311 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 offers multiple cottages with a total average guest review rating of 9.8. Oak Street Cottages is a good option if you prefer nature and a relaxing pace. Visitors staying at this 3-star stay will have use of a barbecue grill and a fireplace. The Retreat At Oak Knoll ~ Pet Friendly is another popular choice. This 4-star cottage has a yard and a garden.

How many cottages are there in Ashland?

Pack your suitcase and pick from 126 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?

Settle in at Oak Street Cottages, a 3-star cottage just a quick drive from downtown. Conveniences here include WiFi and a fireplace. Another family-friendly pick where you can swap the urban jungle for nature is The Retreat At Oak Knoll ~ Pet Friendly. A fireplace and a barbecue grill help make this 4-star cottage a hit with guests. Ashland boasts an array of family-friendly attractions to visit that'll entertain the kids. North Mountain Park and Emigrant Lake promise a fun-filled day for visitors of all ages.

Are there any 5-star cottages in Ashland?

Ashland does not have any 5-star cottages — but you and the crew can still have a stylish stay here! Why not have a look at C' Street Station - Short Walk To Osf? Located about 0.5 mi from the downtown area, this 4-star retreat comes with a fireplace and free WiFi. The Retreat At Oak Knoll ~ Pet Friendly is another terrific 4-star pick just 3 mi from central Ashland. It offers a stress-free vibe close to nature on top of conveniences like a living room and a garden.

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.

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Ashland cottages

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

2. Charming carriage house in Ashland near downtown

3. The Ashland Cottage, walk to town

4. Courtside Cottage - WalkScore 93 - Dog Friendly

5. Paschal Winery

6. Downtown Mint

7. Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

8. Rosewood Studio | Private Cottage Near Downtown

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

10. Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville

11. Charming Jacksonville Studio with AC • Easy Walk to Town & Britt Festival

12. Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.

13. 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.

14. Historic Bradshaw House!

15. Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville

16. 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.

17. 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.

18. The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville

19. Fireside Cottage in Downtown Jacksonville

20. Forest Cabin by Crater Lake & Klamath Falls

Find holiday rentals that suit your style

Top Ashland Hotel Reviews

Ashland Hills Hotel & Suites

Find out more about Ashland

Ashland Cottages information

Frequently asked questions

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