Holiday Homes in Jacksonville

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Featured Holiday Homes in Jacksonville

Railroad District, steps to downtown, everything you need to enjoy Ashland!

10.0 out of 10, Exceptional, (136)
"Clean. Tidy. comfortable. Well appointed. But we left a pair of walking polls behind and would like Sugar to keep them for us and we will pick them up when we stay again in the fall of 2025. David Roberts"
Railroad District, steps to downtown, everything you need to enjoy Ashland!

Premier Downstairs Flat in Perfect Down Town Location

10.0 out of 10, Exceptional, (47)
"This was a beautiful and clean home in a perfect location. So close to downtown and the Shakespeare Festival. The walk was easy, well lite and safe. The home was clean and the beds were comfortable. We would definitely recommend and return!!"
Premier Downstairs Flat in Perfect Down Town Location

Charming home, w/hot tub, close to downtown Pet-Friendly!

10.0 out of 10, Exceptional, (32)
"We had a one night stay at this property with our two dogs on our way to Southern California and met all of our needs. Wonderful fence yard front and back of the house. Wonderful communication with the manager/owner. We had a great time."
The price is AU$774
includes taxes & fees
23 Jan - 24 Jan 2025
Charming home, w/hot tub, close to downtown Pet-Friendly!

The Rellik House and Winery

3.5 star property
10.0 out of 10, Exceptional, (2)
"A perfect place to enjoy the winery and countryside! Staff were responsive and friendly!"
The price is AU$538
includes taxes & fees
12 Jan - 13 Jan 2025
The Rellik House and Winery

Pet-Friendly Medford Vacation Rental w/ Yard!

9.2 out of 10, Wonderful, (7)
"Great cozy location"
Pet-Friendly Medford Vacation Rental w/ Yard!

Jacksonville Mountain Retreat

9.6 out of 10, Exceptional, (61)
"This is a very nice home. "
Jacksonville Mountain Retreat

The Phoenix House- a place to relax and rejuvenate

8.8 out of 10, Excellent, (6)
"We have stayed there twice now. Our art gallery reception was last night in Medford. Today I visited a friend in Ashland. Debbie’s Diner is very close for breakfast and Starbucks down the road. The house has an elegant feel to it, high ceilings and lots of windows to the backyard. Thank you so much."
The Phoenix House- a place to relax and rejuvenate

ZZ ZANY ZOO II - Townhome, with Carport & Garage

10.0 out of 10, Exceptional, (78)
"Fun place, clean, quiet. Great host. "
ZZ ZANY ZOO II - Townhome, with Carport & Garage

Hanna's House | 1 block to downtown!

10.0 out of 10, Exceptional, (160)
"This is a wonderful little space that's within a block of old town Ashland and all its restaurants, coffee shops, and theaters. Wonderful helpfulness and communication from our host, and the space had everything we needed - all with modern remodeling, it seems. We loved it!"
The price is AU$472
includes taxes & fees
12 Jan - 13 Jan 2025
Hanna's House | 1 block to downtown!

California Cottage: Downtown!

9.6 out of 10, Exceptional, (19)
"The property was so cozy. Exactly like the listing description. Literally a few steps from downtown Jacksonville. Everything that we hoped for!"
The price is AU$431
includes taxes & fees
26 Dec - 27 Dec
California Cottage: Downtown!

230-Downstairs-Duplex-Private Bathroom-Mountain View

9.8 out of 10, Exceptional, (17)
"Quiet neighborhood; convenient parking; great HVAC system; comfy beds; hot shower; good wine. Owner gives codes day of stay. "
230-Downstairs-Duplex-Private Bathroom-Mountain View

Cheerful 3-Bedroom home in Central Point

10.0 out of 10, Exceptional, (17)
"This house is in a very nice, quiet neighborhood but really centrally located to surrounding amenities. A beautiful and clean home - love the way it is decorated!! Jill was a great host. Her response time to any communication was almost instant."
Cheerful 3-Bedroom home in Central Point

Brookdale Meadows sleeps 6

10.0 out of 10, Exceptional, (14)
"Four adults stayed at the house. We were in Medford to visit our family matriarch. We enjoyed spending the evening together cooking dinner, sharing a meal and visiting. The house is the best! Clean, comfortable and so well appointed with quality linens, towels abd cookware."
Brookdale Meadows sleeps 6

Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.

10.0 out of 10, Exceptional, (13)
"This is such a lovely getaway! We really enjoyed the space, the beds were super comfy, everything was super clean, and the addition of a bunch of available indoor annd outdoor games and toys really took it up a notch! We had 2 under 2yo kiddos with us who also really seemed to enjoy the space and feel right at home! The hosts were communicative and so kind. We would love to see the check-out instructions displayed more clearly as we found it hard to decipher just that pertinent information! We...
The price is AU$410
includes taxes & fees
26 Dec - 27 Dec
Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.

Sun Cottage Downtown Jacksonville

10.0 out of 10, Exceptional, (14)
"Cute little cottage. Great location for exploring Jacksonville and the surrounding areas. You can easily walk to all the shops, restaurants, Britt Amphitheater and nature trails. The host is also very responsive. "
The price is AU$532
includes taxes & fees
1 Jan - 2 Jan 2025
Sun Cottage Downtown Jacksonville

1 king bed 1 queen bed 2 bedroom house with AC, WiFi and washer and dryer

2.0 star property
10.0 out of 10, Exceptional, (3)
"Highly suggest. Very clean, easy to get in, effortless process. "
The price is AU$389
includes taxes & fees
12 Jan - 13 Jan 2025
1 king bed 1 queen bed 2 bedroom house with AC, WiFi and washer and dryer

Cedar Wood Mountain View Retreat

10.0 out of 10, Exceptional, (2)
"Very easy access to the Shakespeare Festival. Great loft for sleeping and night-gazimh"
Cedar Wood Mountain View Retreat

Serene Riverfront Escape w/ Hot Tub & Views!

9.8 out of 10, Exceptional, (41)
"The house is a great location with an amazing river view. The house was well stocked with plenty of Kitchen and bathroom needs. Very roomy and cozy. We will be back!"
Serene Riverfront Escape w/ Hot Tub & Views!

Southern Oregon Gem (EV Charger)

10.0 out of 10, Exceptional, (35)
"Great spot. Loved the fenced in yard for the dog and toddler. Parking easy. Felt safe. The house was spacious, clean, with comfortable beds. "
The price is AU$246
includes taxes & fees
23 Jan - 24 Jan 2025
Southern Oregon Gem (EV Charger)

The Red Dragon House

10.0 out of 10, Exceptional, (84)
"A truly wonderful home away from home. A great space that feels like a stay out in the country, but just a 10 minute drive to all that downtown Ashland has to offer. The best stocked vacation rental we’ve ever stayed with. The attention to detail to make our stay as comfortable and enjoyable as possible was evident in every aspect of the home. All with plenty of space to spread out, inside and out."
The price is AU$327
includes taxes & fees
5 Jan - 6 Jan 2025
The Red Dragon House
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.
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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, (34)
"Great location, just minutes walking to downtown Jacksonville and the britt festival."
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, (28)
"Awesome location, close to great dining and shopping venues"
The price is AU$357
includes taxes & fees
29 Dec - 30 Dec
A Cowslip's Belle Inn

Charming home, w/hot tub, close to downtown Pet-Friendly!

10.0 out of 10, Exceptional, (32)
"We had a one night stay at this property with our two dogs on our way to Southern California and met all of our needs. Wonderful fence yard front and back of the house. Wonderful communication with the manager/owner. We had a great time."
The price is AU$774
includes taxes & fees
23 Jan - 24 Jan 2025
Charming home, w/hot tub, close to downtown Pet-Friendly!
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.