
Cottage holiday rentals in Ashland
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Ashland
Guests agree: These cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Ashland cottage rentals
Cottage rentals with a hot tub

Paschal Winery - Dream 1 Cottage
Lovely place. The directions from the host are very helpful-our GPS alone got us close but not quite there. One quick warning-the bathroom doors are sliding barn style doors and don’t lock. This is absolutely fine if you’re with other adults-they stay closed if you leave them alone-but a child, or in our case, a small dog with separation anxiety, can leave you with some unexpected exposure that could be a little awkward. I was very glad we were meeting family, not staying with them. That aside, the cottage was lovely. It has a small fenced area that was awesome to let us and the beasties hang out off leash.

Riverfront House with hot tub, game room and more!
This home is in a beautiful location along the Rogue River. it is very lovely with ample space and fun things to do. We loved it here.

R&R Overlooking the Rogue | 2 bed | Hot Tub
Great place to stay and relax! Would definitely visit again!

Paschal Winery - Dream 2 Cottage
This property is breathtaking. The sunsets over the vineyard is incredible. Agnieszka in the winery is wonderful. The cottage we stayed in was updated and clean. The host was flexible and everyone on property was welcoming and knowledgeable. We stumbled upon a member dinner and it was magical. The beds were comfortable we had great water pressure! Would highly recommend. Will absolutely visit again.

Paschal Winery – Paschal Compound
Pet-friendly cottage rentals

Quiet Charming Cottage by Wineries
Very cute cottage. Nice little fenced yard. Wonderful host.

ABBOTT'S COTTAGES- Lark
This is a great location if you want to be right near downtown Ashland! It is easy to walk to Lithia Park, restaurants, groceries, shops, etc. Very quaint, rustic and relaxing, right next to Ashland Creek and fun little art galleries. We would definitely stay here again.

Cheerful cottage in Southern Oregon
From watching the sun rise with my coffee in the morning to watching the sun set with a glass of wine in the evening, Mary's cottage was a peaceful country getaway! I thoroughly enjoyed my stay!

Cozy Modern Cottage
My husband and I stayed here for a month to explore Ashland because we plan to move there and wanted to make sure it was a good fit! We loved Ashland, so much live music, nice people, nature to hike! This airbnb was perfect while we explored! We could walk down to the plaza and coffeeshops, restaurants all within walking distance. The space had everything we needed for an extended stay! I would definitely recommend!

Eagles Nest on the Rogue River
what a beautiful location. river view was beautiful, river access is a little tough, but managed. Steve and Jayne are super friendly and although they live above, we really never heard them. It was a great stop for our mini Vaca and would love to revisit.

Casa Pingla Guest House
A tranquil setting, magnificent surroundings, beautiful house, and Elizabeth and Richard are particularly gracious hosts: what more can I say? My daughter and son appreciated easy access to Mt Ashland Ski Area only 15 miles away. Can’t wait to come back again. Pierre

Oak Hideaway Cottage
The cottage was perfect for our stay in Ashland. It was comfortable and cozy and we will definitely stay again when we visit Ashland in the future.

Bluemoon Vacation Rentals - Bluemoon Cottage
We loved our stay. I was very comfortable and the parking was a dream!
Private cottage rentals

Garden Cottage sleeps five w/2 full baths downtown
I love this house. It’s in such a nice part of Ashland. The inside is very pleasing and so clean. We spent a lot of time sitting in the warm weather on the porch drinking tea or wine. Walking distance to the Shakespeare festival and good restaurants. Very close to the co-op and good coffee shops. Highly recommend staying here for a vacation or longer.

Comfy/Cozy/Cheery/No Steps/EV Car Charger Garage
Loved staying here! Really appreciated the fully equipped kitchen and the dishwasher -- we did most of our own cooking on this trip. Very comfortable for the three of us (me on my own this time, with married friends). Well-designed layout -- private and quiet for all of us. Plenty of lounging space and we enjoyed the Roku TV/streaming in the evenings. Easy, quick drive to our event venue (the fairground buildings), and we loved the EV charger in the garage since we took my friends' EV for this trip. Worked out really well! Enjoyed sunsets from the small deck, and even painted out there one evening when it was still warm out (we were there for the Watercolor Society of Oregon's spring convention). Would wholeheartedly recommend Sheri's place for a stay in Grants Pass. It's close to town, which has lots of good places to eat, shop, see wonderful art galleries, etc. If I'm ever back in Grants Pass I'd love to stay here again!

Beautiful cottage w/pool in bamboo forest
We had a peaceful time. Our niece got married on the property. We could easily walk to the big farm house and then walk back to the cottage. The beautiful bamboo blocks all the noise from the road and the guests at the other house. It is a lovely setting and very comfortable.

Lily Pad/#1 Best Location/Full Kitchen/Luxurious
Beautiful cottage, professionally appointed with modern appliances and furnishings. The location is perfect, off the main road but so close to coffee (award winning Cerberus), restaurants, parks, and shopping.

Historic Bradshaw House!
Amazing location! Walkable shops, restaraunts and grocery store. Right across the street from the trolley stop and only 30 minutes to jetboating and vineyards outside town. Highly recommend this clean beautiful home for some extra privacy in comparison to the local hotels and b&best. Would absolutely stay again! Great communication and quick response from the owners. Easy check-in and out.

Light bright & sparkling clean! Walk to town. Deck
I very much enjoyed my recent long weekend at Lisa and Craig's Ashland cottage. I've visited Ashland many times, but was not acquainted with this area of town. I really enjoyed walking in the residential neighborhood, as well as strolling to the plaza and to plays at OSF. A really lovely area, with a quiet and peaceful vibe. Lisa was very friendly and proactive with communication. Check-in was clear and simple and everything was as described. The cottage was roomier than I had expected and perfect for my weekend stay. Check-out was equally effortless and it was nice to meet the hosts as I departed. Would definitely stay at this Ashland cottage again. Thanks, Lisa and Craig!

Cottage B with Private Patio
My wife and I would stay here again for sure...super perfect location for doing all things Jacksonville

Rogue River Retreat
This was a wonderful Airbnb vacation with great hosts and a beautiful cottage in an idyllic location. I particularly appreciated the thoughtfulness of having the cottage unlocked and heated on arrival because by that time I'd been awake for over 24 hours and just wanted to get inside and relax.
Quick stats about cottage rentals in Ashland
Total rentals
10 properties
Nightly prices starting at
$77 AUD before taxes and fees
Total number of reviews
2.2K reviews
Wi-Fi availability
10 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
Local attractions
Lithia Park, Oregon Cabaret Theatre and Noah's River Adventures
Destinations to explore
- Southern Oregon Holiday rentals
- Medford Holiday rentals
- Crescent City Holiday rentals
- Brookings Holiday rentals
- Crater Lake Holiday rentals
- Grants Pass Holiday rentals
- Klamath Falls Holiday rentals
- Mount Shasta Holiday rentals
- Gold Beach Holiday rentals
- Portland Holiday rentals
- Gold Country Holiday rentals
- Northern California Holiday rentals
- Rentals with outdoor seating Ashland
- Rentals with breakfast Ashland
- Rentals with a patio Ashland
- Private suite rentals Ashland
- Rentals with an EV charger Ashland
- Pet-friendly rentals Ashland
- Apartment rentals Ashland
- Rentals with a hot tub Ashland
- House rentals Ashland
- Cabin rentals Ashland
- Rentals with pools Ashland
- Condo rentals Ashland
- Rentals with a fire pit Ashland
- Guesthouse rentals Ashland
- Family-friendly rentals Ashland
- Rentals with a washing machine and dryer Ashland
- Rentals with a fireplace Ashland
- Kid-friendly rentals Ashland
- Cottage rentals Jackson County
- Cottage rentals Oregon
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom