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Featured Cottages in Jacksonville

Ashland's Mountain View Vacation Rental.
10.0 out of 10, Exceptional, (29)
"This was a great place to stay with wonderful hosts. It was clean and spacious and just a few minutes from downtown Ashland. We would certainly stay here again. "
Ashland's Mountain View Vacation Rental.
Paschal Winery
4.5 star property
9.0 out of 10, Wonderful, (2)
"I loved the isolated RV with a gorgeous view of the pond and the swans were absolutely gorgeous. The rv was in great condition and very comfortable. My only suggestions would be to leave stove directions and label the knobs better. My mother in law struggled turning it on and off. We also had an alarm sound during the night a couple of times and it wasnt related to the gas. Maybe humidity? A towel for the bathroom floor would have been useful and less throw pillows to find homes for. But...
The price is NZ$335
includes taxes & fees
1 Oct - 2 Oct
Paschal Winery
Blue Gate Cottage on the Rogue River
9.8 out of 10, Exceptional, (24)
"A family with a new baby attended a birthday party involving the Lodge next door, also a VRBO property. Their baby was celebrating his first birthday, and his great grandmother staying next door was celebrating her 87th birthday. These two venues were perfect for the occasion. The setting was beautiful, there was plenty of room to relax with full kitchen access. You can't go wrong renting these two Rogue River hideaways together!"
Blue Gate Cottage on the Rogue River
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
10.0 out of 10, Exceptional, (80)
"We enjoyed a delightful stay for our Britt Festival concert dates. Our hosts provided everything we needed for a relaxing, pleasant, and comfortable stay. The home was pleasantly cool as temperatures soared to over 100°. The linens, dishes, book collection, gym equipment, and grounds were perfectly accommodating. We especially enjoyed walking to nearby (delicious) restaurants for our meals to avoid cooking in the heat. Fantastic time! We will be back. Highly recommend! "
The price is NZ$259
includes taxes & fees
25 Sept - 26 Sept
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Adorable 2 bedroom 1 bath Craftsman Cottage in Downtown Grants Pass
9.4 out of 10, Exceptional, (76)
"This was a pleasant and convenient place to stay while we were visiting with family in Grants Pass, OR."
Adorable 2 bedroom 1 bath Craftsman Cottage in Downtown Grants Pass
Courtside Cottage - WalkScore 93 - Dog Friendly
10.0 out of 10, Exceptional, (32)
"Three nights. Two seniors and a mini schnauzer. The cottage is exactly as advertised. The location is excellent. The owner is engaging but respectful and not intrusive. Flexible in& out times if needed and available. Will stay here again if in the area. "
The price is NZ$528
includes taxes & fees
24 Sept - 25 Sept
Courtside Cottage - WalkScore 93 - Dog Friendly
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
9.6 out of 10, Exceptional, (11)
"The property was adorable. We enjoyed spending time down at the river."
The price is NZ$311
includes taxes & fees
26 Sept - 27 Sept
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
The Inn on 5th Street!
9.6 out of 10, Exceptional, (71)
"This house was perfect for what we were looking for. It had an old timey charm just like the town of Jacksonville and across the street from a grocery store. Everything was walking distance. Fully equipped kitchen, better than any place I’ve rented. A basket a complimentary snacks and a local wine was included, bonus! The keypad is a little tricky but the host was quick to resolve the issue. Good communication. Beds were comfy and bedrooms were separated enough to have distance from your family...
The Inn on 5th Street!
Grants Pass Hillside Retreat w/View Mins from Everything
9.4 out of 10, Exceptional, (14)
"Our stay was short but the location was beautiful and easy to find. Jen was very responsive, helpful, and super kind!! Very cute room for two, overall would absolutely book again. ❤️"
The price is NZ$177
includes taxes & fees
24 Sept - 25 Sept
Grants Pass Hillside Retreat w/View Mins from Everything
Cozy private family ranch cottage! Vineyards, Britt Festival and Applegate Lake!
10.0 out of 10, Exceptional, (5)
"We were very happy with our stay at the Guches Ranch! The property was very well maintained, clean, and comfortable. It was perfect for my family and I."
Cozy private family ranch cottage! Vineyards, Britt Festival and Applegate Lake!
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
The price is NZ$379
includes taxes & fees
30 Sept - 1 Oct
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
The Cottage!
2.0 star property
7.0 out of 10, Good, (2)
"Cute cottage for 1 or 2 people. It was 100 degrees outside but the AC worked great to keep it cool inside. The kitchen is fully equipped with everything to cook a nice meal. Nice clean decor and linens. Located just 1/2 block from shops and restaurants, walk everywhere easily including Britt Fest. Friendly town with a nice variety of things to explore including nearby hiking trails."
The Cottage!
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
10.0 out of 10, Exceptional, (3)
"Although a bit hard to find, Casa Amore is perfect for a holiday in Ashland, Oregon. My husband, adult daughter, and family dog spent 3 nights there and we all were very comfortable. It’s the perfect location if you plan on seeing plays at OSF or doing some fly fishing with the Ashland Fly Shoppe. The neighborhood is peaceful and safe with great places to walk your dog. We liked having two bathrooms and a fully functioning kitchen. We would stay again on our next visit. "
The price is NZ$459
includes taxes & fees
1 Oct - 2 Oct
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
Family friendly home overlooking the Rogue River.
9.0 out of 10, Wonderful, (12)
"Enjoy our stay a little disappointed there was dog poop everywhere in the yard someone left behind, the patio and porch we had to clean. and then we went to cook with the grill and it was really dirty so we cleaned that we pulled plates tfrom the cupboard and they were full of water, and my husband got water all over them enjoyed our stay but a little disappointed"
The price is NZ$385
includes taxes & fees
24 Sept - 25 Sept
Family friendly home overlooking the Rogue River.
The Vintage Cottage with riverfront access
9.8 out of 10, Exceptional, (89)
"Love the location and host was great"
The price is NZ$343
includes taxes & fees
1 Oct - 2 Oct
The Vintage Cottage with riverfront access
Downtown Mint
10.0 out of 10, Exceptional, (27)
"Clean, comfy, and pleasant! I would come back again! "
The price is NZ$352
includes taxes & fees
23 Oct - 24 Oct
Downtown Mint
Newly built private cottage-Private Pool, Romantic Oasis, wineries & restaurants
10.0 out of 10, Exceptional, (5)
"We were thrilled with our stay here. The property and amenities are beautiful. The hosts were friendly and helpful. The home had everything we needed and more. We would definitely stay again and highly recommend this property!"
Newly built private cottage-Private Pool, Romantic Oasis, wineries & restaurants
TIGERS DEN - #1 BEST LOCATION, ROMANTIC, STUNNING, STEPS TO BRITT FESTIVAL
10.0 out of 10, Exceptional, (33)
"My only complaint is that there were no sheets for the sofa bed. There were plenty of blankets & pillows :) but when we returned from our fun time at the concert and hoped for a good night’s sleep, it was disappointing to not find sheets anywhere. And it was too late to message the host or I would’ve done that. Otherwise, we loved this place and would stay again. Location is ideal and beautiful grounds as well."
TIGERS DEN - #1 BEST LOCATION, ROMANTIC, STUNNING, STEPS TO BRITT FESTIVAL
Tranquil setting surrounded by panoramic mountain views, grazing horses
9.8 out of 10, Exceptional, (104)
"Lovely stay in 2 bedroom cottage. Very comfortable. Well-appointed kitchen with everything needed to cook if desired. Local dining options at Phoodery food carts in Phoenix. Hosts were wonderful: friendly and helpful, yet respectful of privacy. Highly recommended."
Tranquil setting surrounded by panoramic mountain views, grazing horses
The Ashland Cottage, walk to town
10.0 out of 10, Exceptional, (184)
"Comfortable bed, private home, stocked kitchen, peaceful area. Host has been very helpful. We’ll be back."
The price is NZ$470
includes taxes & fees
7 Oct - 8 Oct
The Ashland Cottage, walk to town
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Other property types in Jacksonville

TIGERS DEN - #1 BEST LOCATION, ROMANTIC, STUNNING, STEPS TO BRITT FESTIVAL
10.0 out of 10, Exceptional, (33)
"My only complaint is that there were no sheets for the sofa bed. There were plenty of blankets & pillows :) but when we returned from our fun time at the concert and hoped for a good night’s sleep, it was disappointing to not find sheets anywhere. And it was too late to message the host or I would’ve done that. Otherwise, we loved this place and would stay again. Location is ideal and beautiful grounds as well."
TIGERS DEN - #1 BEST LOCATION, ROMANTIC, STUNNING, STEPS TO BRITT FESTIVAL
A Cowslip's Belle Inn
3.0 star property
9.8 out of 10, Exceptional, (24)
"Love love loved it. Perfect walkable distance for the Shakespeare plays in Ashland "
The price is NZ$266
includes taxes & fees
15 Oct - 16 Oct
A Cowslip's Belle Inn
Creekside Cabin--a quiet, wooded country delight
10.0 out of 10, Exceptional, (165)
"Lovely little, cozy cabin. "
Creekside Cabin--a quiet, wooded country delight
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do cottages in Jacksonville cost?
Rates for cottages in Jacksonville range between NZ$177 and NZ$528 per night. Whatever your budget, you’re sure to find an ideal place to soak up nature’s beauty. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Jacksonville?
Enjoy nature’s beauty in one of the 107 cottages available in Jacksonville. To help you find your ideal stay, use our handy filter tool to search for perks or amenities you prefer.
What is there to do in Jacksonville near my cottage?
No matter your tastes or interests, Jacksonville has plenty of things to keep you occupied. Red Lily Vineyards, Valley View Winery and Fiasco Winery are on many visitors’ sightseeing itineraries. Don’t forget to explore Devitt Winery and Vineyards, Cricket Hill Winery and Quady North either. With Expedia’s Jacksonville hotel deals, you’ll be able to discover even more popular attractions like these with the cash you save.