
Tiny house vacation rentals in Jackson County
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Top-rated tiny house rentals in Jackson County
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" sweet little garden studio "
The studio is a cozy snuggery! Some highlights: super comfortable bed, fun art in bathroom, cute flannel sheets with woodland creature print. But the best part was GG herself. Even before I got to town, she was able to give me insider information….the restaurant I wanted to visit would be closed on that day. Then, the night I arrived I took several wrong turns on my way to the property and needed a LOT of help from her to find my way. GG even stood outside the house on that bitterly cold night to guide me in. So kind and helpful! A wonderful experience!

The Greenwood Villa w/wood fire hot tub
We absolutely loved our stay the first time, so wanted to come back for our honeymoon! Jonathan and his family were so welcoming into their beautiful home, we will absolutely be returning!

High Street Cottage, Artist's Garden Cottage
Beautiful cottage, a nice walk into town and the Shakespeare festival. Cozy but very doable for 4 adults. Sometimes when I go to a place that seems fancy, I feel like I’m tip toeing around - this space was beautiful and very comfortable - I was able to truly relax during my stay. Wish we had booked an extra day just to enjoy the garden and enchanting space! Hope we will be able to return!

Historic Cottage close to plaza
My daughter and I had a wonderful stay at Julie’s cottage. The location was perfect for visiting Ashland. Private and peaceful yet close to downtown. The cottage was immaculate and so comfortable. We would love to come back!
Tiny house rentals with a patio

Modern Tiny stay in the country
This stay was quiet, relaxing, and super comfortable. While my wife and I are tall people (6’1 and 5’10) we fit comfortably in the loft, on the couch, and sitting around the outdoor fire. The wildlife was abundant and the outside area was so nice to use. Thank you for creating such an inviting and relaxing stay!

River front tiny house
Enjoyed our stay, my daughter loved the lofted. Her only complaint was the window in the loft didn't have a black out shade like all the rest of the windows. the tiny home stayed warm, the water stay hot. Great TV. no wifi , so bring a hot spot ir use our mobile hotspot. we did and it worked great. we'll stocked on kitchen utensils, had Starbucks k cups for coffee. we enjoyed that alot. Loved the jacuzzi. the location was great, on the rouge river . semi fenced and gated . felt safe here. all in all we enjoyed our stay. we are looking forward to renting again for the next time we visit grants pass. Thank you Curtis & Amy.

Walk to town! Cozy Forest Teeny House
Oak Street Meadow was everything I needed for my short visit to SOU for a training. Bed was comfy, easy to find even in the dark, available parking, and easy and clear instructions! It was toasty even with being in the 30*s outside, so no worries there if traveling in the colder times. I will just add that if you are a light sleeper I would bring earplugs because it was noisier than I anticipated!! Thanks for the cozy teeny house to keep me safe for the night :)

Kelly’s Carriage House 4 miles from Ashland
We are so impressed by this place, it’s everything that we wanted and much more! The farm is so beautiful, the animals adorable and Carriage House is so comfortable! The hosts are amazing people, super friendly and kind. I can’t wait to go back and I will recommend to all my families and friends. Thank you Chace and Kelly!

The Crows Nest + Complimentary Farm Breakfast
We are so thankful for the great people who hosted us while house hunting. We and our dog had a lot of fun watching the sheep, goats and turkeys. The scenery is incredibly beautiful. Listening to the creek at night was so peaceful. There are many great restaurants in town which is just a quick trip away. We would definitely stay here again.

Eco Tiny Home A-Frame Lakeside
The house was well stocked in the kitchen and had lots of spices and cooking basics to use. Plenty of utensils, pots/pans, glasses, plates, etc. Great use of space, cozy, good ambiance - everything you need for a quick stay. Hot water ran out about 2-3 mins into a shower. We found some dust and a couple bugs but when you’re out on a farm, that’s to be expected.

Broken Chair Ranch Bungalow
Wonderful place to stay! Very peaceful and quiet. Lots of outdoor activities nearby too, which is why we stayed. Thank you so much!

Tiny Groove with plunge pool and soaking tubs
This was such an amazing stay! It was so nice to get away and sun bathe, stargaze, and relax. The view is absolutely gorgeous, the amenities (soaking tub, sauna, etc.) were perfect and exactly as described! Christine was very responsive and clear with instructions. We will definitely be back! Thank you for the beautiful getaway.
Tiny house rentals with outdoor seating

Tree Top Studio
It is an amazing stay if you want that off grid, not connected with anything, phone , TV, internet .... this is the place. The walk down to the river is long and steep in some parts, but worth the walk. Everything is perfect, would not change a thing.

Modern Getaway on Sunflower Farm
What a beautiful little home with all the thoughtful touches that really show the host cares. We had farm fresh eggs in the fridge, all the kitchen basics needed to cook, some snacks and nice teas to enjoy! And the location was super convenient to get to restaurants, wineries and anywhere else in the valley that we needed to go. Would definitely recommend staying!

Octagon Studio / Beautiful Rogue River property
Beautiful setting - right on the river. Jerry was kind and helpful.

Little Big Tree Cabin
This place was unbelievable, a Cabin heaven. It was about 50 minutes from crater lake and a beautiful drive. The actual house is stunning, so clean, so cozy, anyone can see why the second they walk in! So grateful to have found this and been able to stay there for two nights.

Escape to tranquility at the Tiny House
This was a perfect location to tour the nearby wineries. The host was easy to communicate with and friendly. It was private, easy to find, and had all the amenities we needed. We would absolutely stay here again.

🥂The Applegate Spa🥂
Such a cute little home away from home! My husband and I went to celebrate turning 40 and had the best time! We loved the hot tub, the massage chairs and how cute and private everything was! Nice walking trails nearby and really good food all around. Enjoyed one of the local wineries down the street and the fire pit at night in the rain! Thanks to the hosts for being so accommodating of their space!

Blue Gate Cottage on the Rogue River
I would not hesitate to stay here again. So peaceful and beautiful. The road to the cabin isn’t paved, but I didn’t have any trouble making it there in my smaller car, even on rainy days. Couldn’t ask for a better spot than right on the river.

Charming very well appointed cottage !
One of the best stays I’ve had in a long time—truly wish I could live here! The host was incredibly accommodating and quick to respond, making everything seamless from start to finish. I originally came hoping to catch up on some laptop work, but this beautiful cottage was so thoughtfully designed for rest and rejuvenation that I ended up unplugging completely—playing guitar, soaking in the cozy atmosphere, and loving every minute of it. You can genuinely feel the love and care poured into every corner of this space. With stunning mountain views, thoughtful amenities, the largest and most comfortable bed you can dream of and peaceful surroundings, it’s the perfect place to relax, reset, and enjoy everything Ashland and the local area have to offer. I honestly can't recommend Ashland Farm enough—this place is pure magic.
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