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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, 46 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 stars1 week 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 stars2 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, 62 reviews

FARMHOUSE COTTAGE

AronRating, 5 stars5 months ago
This was our second visit to this property. Our first one was just for a night, I think; this time we had 4 nights, and it holds up for a longer stay. It's a quiet and peaceful spot at any time; this time the hosts were away, so we had the entire property to ourselves. The location is simultaneously rural and isolated, and conveniently central to Ashland, Talent, Phoenix, Medford, and Jacksonville. The cottage is comfortable and well appointed. The kitchen is compact, but not frustratingly so - we were able to do the amount of cooking we wanted without issue. The whole space worked well. We enjoyed are stay and would be happy to return again.
Guest favorite
Cottage in Ashland
4.87 out of 5 average rating, 55 reviews

Light bright & sparkling clean! Walk to town. Deck

CynthiaRating, 5 stars9 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, 35 reviews

Paschal Winery - Dream 1 Cottage

JennyRating, 5 stars3 weeks ago
What a beautiful place right on a vineyard. Loved all of the seating around the house and property. The room was nice and comfy. We didn’t make food but it looked as though everything was there. The family who owns the vineyard were so sweet and hospitable. Would definitely rebook for another trip!!!
Cottage in Grants Pass
4.81 out of 5 average rating, 307 reviews

Riverfront House with hot tub, game room and more!

NickRating, 5 stars1 month ago
The house and location was amazing! What an awesome back yard right on the river, huge deck and clean hot tub and bbq. We will definitely be visiting here again when we're in town.
Superhost
Cottage in Gold Hill
4.77 out of 5 average rating, 415 reviews

Rogue Rivers Edge | 1 BR Fishing Inspired Cottage

TashfinRating, 5 stars1 week ago
Wonderful host and the place was exactly as advertised. Had a great stay. Highly recommend and will definitely stay there again when visiting.
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 stars1 week ago
Great place to stay and relax! Would definitely visit again!
Superhost
Cottage in Talent
4.81 out of 5 average rating, 27 reviews

Paschal Winery - Dream 2 Cottage

RichelleRating, 5 stars2 weeks ago
Loved staying here! The place was located on such beautiful property. :) The airbnb was clean and well maintained. Great amenities including hot tub, fenced backyard, comfy beds, and lots of room. Would stay again!
Superhost
Cottage in Talent

Paschal Winery – Paschal Compound

Pet-friendly cottage rentals

Superhost
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, 447 reviews

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

HarrietRating, 5 stars2 weeks ago
This was the third time we have stayed at this location. We are 2 adults traveling with a dog and feel that all our needs were met. Having a second bathroom is a real plus . The kitchen is large enough to cook your own dinner and refrigerator space is plentiful. This cottage is very cute and we would stay 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!
Guest favorite
Cottage in Ashland
4.95 out of 5 average rating, 155 reviews

ABBOTT'S COTTAGES - Falcon

LawrenceRating, 5 stars3 weeks ago
Lovely 2-2 in a safe area of Ashland within walking distance to the Food Coop and all the plays.
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 stars8 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 stars2 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

    G$10,491 GYD 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