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Cottage vacation rentals in Ashland

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Popular amenities for Ashland cottage rentals

Cottage rentals with free parking

Top guest favorite
Cottage in Ashland
4.98 out of 5 average rating, 47 reviews

Garden Cottage sleeps five w/2 full baths downtown

NoraRating, 5 stars2 weeks ago
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.
Superhost
Cottage in Grants Pass
4.91 out of 5 average rating, 34 reviews

Comfy/Cozy/Cheery/No Steps/EV Car Charger Garage

KathrynRating, 5 stars2 months ago
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!
Superhost
Cottage in Central Point
4.78 out of 5 average rating, 23 reviews

Beautiful cottage w/pool in bamboo forest

TaraRating, 5 stars9 months ago
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.
Guest favorite
Cottage in Jacksonville
4.97 out of 5 average rating, 36 reviews

Lily Pad/#1 Best Location/Full Kitchen/Luxurious

EliseRating, 5 stars2 weeks ago
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.
Top guest favorite
Cottage in Jacksonville
4.89 out of 5 average rating, 79 reviews

Historic Bradshaw House!

MarianRating, 5 stars3 weeks ago
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.
Top guest favorite
Cottage in Phoenix
4.94 out of 5 average rating, 63 reviews

FARMHOUSE COTTAGE

DeannaRating, 5 starstoday
Our stay at the cottage was perfect from check-in to check-out. I stayed with my parents for my nieces graduation; they loved the accommodations and the surroundings. Thank you for a great trip!
Guest favorite
Cottage in Ashland
4.87 out of 5 average rating, 55 reviews

Light bright & sparkling clean! Walk to town. Deck

CynthiaRating, 5 stars10 months ago
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!
Guest favorite
Cottage in Jacksonville
4.97 out of 5 average rating, 32 reviews

Cottage B with Private Patio

Dane & Casey - Sicily, Vienna, GeneRating, 5 stars11 months ago
My wife and I would stay here again for sure...super perfect location for doing all things Jacksonville

Cottage rentals with a hot tub

Guest favorite
Cottage in Talent
4.94 out of 5 average rating, 36 reviews

Paschal Winery - Dream 1 Cottage

MeghanRating, 5 stars2 weeks ago
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.
Cottage in Grants Pass
4.81 out of 5 average rating, 308 reviews

Riverfront House with hot tub, game room and more!

DeniseRating, 5 stars1 month ago
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.
Superhost
Cottage in Gold Hill
4.74 out of 5 average rating, 379 reviews

R&R Overlooking the Rogue | 2 bed | Hot Tub

AndyRating, 5 stars2 weeks ago
Great place to stay and relax! Would definitely visit again!
Superhost
Cottage in Talent
4.83 out of 5 average rating, 29 reviews

Paschal Winery - Dream 2 Cottage

MartaRating, 5 stars2 weeks ago
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.
Superhost
Cottage in Talent

Paschal Winery – Paschal Compound

Pet-friendly cottage rentals

Guest favorite
Cottage in Central Point
4.91 out of 5 average rating, 78 reviews

Quiet Charming Cottage by Wineries

JenetteRating, 5 stars1 month ago
Very cute cottage. Nice little fenced yard. Wonderful host.
Guest favorite
Cottage in Medford
4.94 out of 5 average rating, 450 reviews

Efficient, clean, pet-friendly 2 bed/bath cottage

KarenRating, 5 stars1 week ago
Great place to stay with easy access to the freeway. Very clean and comfortable.
Guest favorite
Cottage in Ashland
4.94 out of 5 average rating, 135 reviews

ABBOTT'S COTTAGES- Lark

ChristaRating, 5 stars2 weeks ago
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.
Superhost
Cottage in Central Point
5 out of 5 average rating, 5 reviews

Cheerful cottage in Southern Oregon

JodyRating, 5 stars12 months ago
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!
Cottage in Ashland

Cozy Modern Cottage

BlakeRating, 5 stars28 months ago
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!
Guest favorite
Cottage in Shady Cove
4.85 out of 5 average rating, 53 reviews

Eagles Nest on the Rogue River

SheriRating, 5 stars9 months ago
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.
Cottage in Ashland
5 out of 5 average rating, 11 reviews

Casa Pingla Guest House

PierreRating, 5 stars39 months ago
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
Superhost
Cottage in Ashland
4.59 out of 5 average rating, 22 reviews

Bluemoon Vacation Rentals - Bluemoon Cottage

SaraRating, 5 stars3 weeks ago
We loved our stay. I was very comfortable and the parking was a dream!

Quick stats about cottage rentals in Ashland

  • Total rentals

    10 properties

  • Nightly prices starting at

    R898 ZAR before taxes and fees

  • Total number of reviews

    2.2K reviews

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

  • Local attractions

    Lithia Park, Oregon Cabaret Theatre, and Noah's River Adventures

Destinations to explore

  1. Airbnb
  2. United States
  3. Oregon
  4. Jackson County
  5. Ashland
  6. Cottage rentals