
Cottage vacation rentals in Jacksonville
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Top-rated cottage rentals in Jacksonville
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Jacksonville cottage rentals
Cottage rentals with a hot tub

Paschal Winery - Dream 1 Cottage
This an incredibly beautiful and peaceful setting! Amazing place to unwind with plenty of adventures nearby!

Hot Tub w/ River Views / Private Patio / Spacious
very conveniently located and super cute inside. bed was very comfortable. I loved being able to hear the river and the hot tub was the perfect touch. the bed was also incredibly comfortable. would definitely stay here again.

Riverfront House with hot tub, game room and more!
The house felt homey and relaxing, with beautiful surroundings that added to the charm. There were plenty of activities to keep our son entertained, which made the stay even better. It was a truly enjoyable experience for our family!

R&R Overlooking the Rogue | 2 bed | Hot Tub
Stayed with Stay Rouge for a week. Communication was great and the response return time was very fast! Would stay again!

Paschal Winery - Dream 2 Cottage
Beautiful location and views of the valley. Didn’t realize it was connected with the winery which was a real plus! Food and wine and service at the winery was spectacular.
Pet-friendly cottage rentals

Quiet Charming Cottage by Wineries
We enjoyed staying here very much! The home is in the country very close to Jacksonville, a very cool old West town. Medford and Cenral Point were just a few minutes away. It was so peaceful and quiet here! Having a full kitchen helped, as we cooked breakfast both mornings of our stay. We will try to book this place again when we are in the area again. Don't hesitate at all, this is a great place with great hosts!

Victorian Garden Carriage House
Margaret was very friendly and responsive to us before and during our stay. The accommodations were just as shown and she left us homemade granola, fresh coffee beans, half & half and fresh fruit. The grounds surrounding the property are so beautiful and a delight to any gardner/ landscape enthusiast or plant lovers. We had everything we needed for a peaceful, relaxing stay. Just two blocks away you are in the heart of downtown with Lithia Park, many restaurants with a great variety of food and drinks options and even desserts. The Shakespeare Theater is right in the middle of this area and surrounded by great shopping. The locals are very friendly and welcoming. I would definitely love to stay at this location again. Margaret and John were great hosts.

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!

The Red Dragon House
The family and I had a wonderful experience staying at The Red Dragon House! The house is clean, the hosts are friendly and responsive, and the location is peaceful. This is a great place to stay if you don't mind being just a few minutes from downtown Ashland - for us, this was preferable. There are thoughtful touches throughout the house, and you can tell the hosts spent time considering the care and comfort of their guests. We've stayed here twice now, and can't wait to return for our next visit to Ashland!

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

Vintage farm house, sleeps 4, peaceful, quite
Sherry’s place was great. It was conveniently located a few minutes outside of town. It was close to the Oregon caves and the redwoods as well. Place is cute and quiet, surrounded by beautiful fields. Thank you! Sherry and Mike
Private cottage rentals

Garden Cottage sleeps five w/2 full baths downtown
Sugar’s cottage was a great place to stay for the holidays with my family. Very cozy and great location.

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.

FARMHOUSE COTTAGE
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.

Standish Cottage on the Creek
Great little cottage within walking distance to all that the charming town of Jacksonville has to offer! Best part is being able to hear the music from the Britt Festival right from the patio. Loved that Margaret provides everything you need for a comfortable stay.

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

Sweet Breeze Bungalow
We visit Ashland twice a year and prefer lodging that allows us to safely park our car for days, while walking everywhere. This fit the bill perfectly. We enjoyed making breakfast & lunches in the cozy kitchen, and enjoyed dinner at numerous top-notch restaurants. As others mention, bed was quite firm but very comfortable for us. Cute, historic cottage with new updates throughout giving you old world charm with modern amenities. Layout and size seem perfect for two. Really appreciated the coffee and cold drinking water options. Would definitely stay here again. We hoped to enjoy the patio area, but rain and cold kept us indoors. Parking area was roomy, safe and easy for our SUV. Thanks for a lovely vaca, Julie!

Warm and Inviting Peaceful, Backyard, Recliner,
Sheri’s place never disappoints. Spotless, beautiful decor, kitchen is fully stocked, and Sheri checked in to make sure all was good. We have stayed here several times and will again in the future!!

Augustino Vineyard Farmhouse Cottage Cave Junction
Lovely stay! The surroundings were beautiful and we enjoyed the front porch coffee in the mornings while gazing at the lovely scenery. The area was super quiet and helpful because I had to do some writing while there, and I wasn't disturbed by highway traffic. The farmhouse is cute and clean. There is a horse on the property but no warning sign that it’s a live fence with electricity, and even with supervision, my ten-year-old daughter was accidentally shocked when she bumped her arm, and it swelled up while we were there for two days. Hopefully, they can post a warning sign for future tenants. We would stay again and recommend this location for friends and family who travel into the area. It's not too far from food or grocery stores, maybe about 12 minutes, and if you enjoy the outdoors you will enjoy it here. We didn't go to the tasting room, but I've been there before and it's just lovely! Great hosts— very kind and responsive.
Quick stats about cottage rentals in Jacksonville
Total rentals
10 properties
Nightly prices starting at
$124 CAD before taxes and fees
Total number of reviews
680 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Britt Festival Pavilion, Bella Union Restaurant, and The Schoolhaus Brewhaus
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