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Compare 229 Vacation Homes in Historic Jacksonville with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (30)
"Very charming home with everything you need to relax and enjoy a vacation in Ashland, Oregon."
The price is SAR 732
SAR 1,884 total
includes taxes & fees
3 Dec - 4 Dec
Charming home, w/hot tub, close to downtown Pet-Friendly!

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

ZZ ZANY ZOO II - Townhome, with Carport & Garage

10.0 out of 10, Exceptional, (76)
"The place was clean and comfortable. Greeted with wine, cheese, fruit and snacks. The host Kathie went above and beyond. I will definitely stay there again. Highly recommend. "
ZZ ZANY ZOO II - Townhome, with Carport & Garage

Charming Retreat: Ashland's Urban Hideaway

9.8 out of 10, Exceptional, (28)
"My husband and I have stayed at many of the rentals in Ashland over the years. We really enjoyed the location of Hellman House. One could walk just about anywhere to dine, have drinks, shop, visit famous Lythia Park. The home was clean, and the property manager was very responsive. My only nitpicky thought is that the upstairs bedroom doesn’t have a door. Kind of odd. Should be easy enough to add one. Our daughter and her fiancé stayed with us two nights, and so we had to be quiet downstairs as...
Charming Retreat: Ashland's Urban Hideaway

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!

The River House with Views of the Famous Rogue River! No cleaning fees!

10.0 out of 10, Exceptional, (23)
"We really enjoyed the stay the location was great close to town but still had a nice country feel, the fall leaves are changing this time of year so it was very pretty."
The price is SAR 755
SAR 877 total
includes taxes & fees
29 Nov - 30 Nov
The River House with Views of the Famous Rogue River! No cleaning fees!

Pet-Friendly Medford Vacation Rental w/ Yard!

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

Entertainment Home on The Golf course - Pool, Hot Tub, Views, & Pool Table

Entertainment Home on The Golf course - Pool, Hot Tub, Views, & Pool Table

New house with king beds and 3 full bathrooms

9.4 out of 10, Exceptional, (28)
"While this property had a few quirks, I really enjoyed this stay a lot. It was so nice to relax after a long day traveling."
The price is SAR 559
SAR 929 total
includes taxes & fees
17 Dec - 18 Dec
New house with king beds and 3 full bathrooms

Comfy Cozy Casa

10.0 out of 10, Exceptional, (35)
"Came in town for a race event house was clean and organized."
The price is SAR 469
SAR 1,107 total
includes taxes & fees
1 Dec - 2 Dec
Comfy Cozy Casa

Spacious Grants Pass Home w/ Hot Tub & Views!

9.4 out of 10, Exceptional, (18)
"The house was wonderful, but I will never use VRBO again if it uses EVOLVE. I want to talk to people when I have a question - not a robot. Also - they need to fix their refrigerator. VERY noisy."
Spacious Grants Pass Home w/ Hot Tub & Views!

Mid Century Modern Guest House

10.0 out of 10, Exceptional, (4)
"Really lovely home, super cozy for a couple and conveniently located. Definitely would stay again. "
The price is SAR 382
SAR 656 total
includes taxes & fees
1 Dec - 2 Dec
Mid Century Modern Guest House

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 price is SAR 1,051
SAR 1,937 total
includes taxes & fees
29 Nov - 30 Nov
The Phoenix House- a place to relax and rejuvenate

Spacious contemporary home nestled in the foothills of RoxyAnn.

10.0 out of 10, Exceptional, (14)
"The owners thought of everything that we might need, it was super clean and beautiful! We will definitely stay again!"
Spacious contemporary home nestled in the foothills of RoxyAnn.

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 SAR 541
SAR 1,262 total
includes taxes & fees
1 Dec - 2 Dec
The Rellik House and Winery

Large kitchen! Quiet Cul-de-sac!

9.2 out of 10, Wonderful, (30)
"Clean and comfortable house. Had all the essentials for our work crew. Thanks for accommodating us. "
The price is SAR 413
SAR 924 total
includes taxes & fees
9 Dec - 10 Dec
Large kitchen! Quiet Cul-de-sac!

Barclay Klum House by WanderLodges

4.0 star property
10.0 out of 10, Exceptional, (4)
"One can truly enjoy family time & dinners ~ kitchen is beautifully equipped ⚜️❄️~ Dining room ~ gorgeous ~ open concept makes space perfect 👍 "
The price is SAR 628
SAR 1,115 total
includes taxes & fees
3 Dec - 4 Dec
Barclay Klum House by WanderLodges

New Downtown 3 Bedroom Upstairs Flat with views

9.6 out of 10, Exceptional, (23)
"The Double Bed Futon on the listing is inaccurate since the couch does not fold out. The property itself was great and perfect for our girl's weekend to see the plays! Within walking distance to the theatres. I liked how the bathrooms had the sinks separate from the toilet and shower room. Great for friends."
New Downtown 3 Bedroom Upstairs Flat with views

Station House Suite A

10.0 out of 10, Exceptional, (11)
"Every detail thought of for an enjoyable stay. "
The price is SAR 971
SAR 1,963 total
includes taxes & fees
30 Nov - 1 Dec
Station House Suite A
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 Historic Jacksonville

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 SAR 558
SAR 832 total
includes taxes & fees
2 Dec - 3 Dec
A Cowslip's Belle Inn

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

10.0 out of 10, Exceptional, (30)
"Very charming home with everything you need to relax and enjoy a vacation in Ashland, Oregon."
The price is SAR 732
SAR 1,884 total
includes taxes & fees
3 Dec - 4 Dec
Charming home, w/hot tub, close to downtown Pet-Friendly!

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
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.