Holiday Homes in Historic Jacksonville

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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Featured Holiday Homes in Historic Jacksonville and around

Downtown Delight: 3BDR Urban Escape
Outdoor dining

Downtown Delight: 3BDR Urban Escape

10.0 out of 10, Exceptional, (15)
"We were a family group in town to visit our sister several miles away. This home was lovely, well-equipped, super comfortable. The neighborhood was very quiet with dedicated parking. The upstairs bedrooms were a bit overheated at night and the floors / stairs creaked as mentioned by other reviewers, but nothing out of the norm for an older house. Will definitely try to stay here again!"
Downtown Delight: 3BDR Urban Escape
Premier Downstairs Flat in Perfect Down Town Location
Fridge, microwave, oven, stovetop

Premier Downstairs Flat in Perfect Down Town Location

10.0 out of 10, Exceptional, (48)
"Great location - close to restaurants and shops! "
Premier Downstairs Flat in Perfect Down Town Location
California Cottage: Downtown!
Fridge, microwave, stovetop, dishwasher

California Cottage: Downtown!

9.8 out of 10, Exceptional, (22)
"We had a fun weekend even though it rained the whole time! We walked a short block and we're right in the downtown area. Great restaurants and fun shopping. The cottage was very comfortable and clean. "
The price is €224
includes taxes & fees
18 Feb - 19 Feb
California Cottage: Downtown!
ZZ ZANY ZOO II - Townhome, with Carport & Garage
Point of interest

ZZ ZANY ZOO II - Townhome, with Carport & Garage

10.0 out of 10, Exceptional, (80)
"Adorable family-friendly theme with holiday spirit made for a memorable vacation."
ZZ ZANY ZOO II - Townhome, with Carport & Garage
232-Duplex-Private Bathroom-Mountain View
TV, DVD player, books, video library

232-Duplex-Private Bathroom-Mountain View

10.0 out of 10, Exceptional, (35)
"This has become our favorite place to stay in Ashland. We go there often to play at Mt. Ashland and to enjoy the Shakespeare Festival. This beautiful condo has everything we need with amazing views and a great coffee shop right across the street. We don't need to drive to enjoy downtown Ashland, everything is walking distance. It really has become a home away from home for us. "
232-Duplex-Private Bathroom-Mountain View
Pet-Friendly Medford Vacation Rental w/ Yard!
Terrace/patio

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
Exterior detail

Jacksonville Mountain Retreat

9.6 out of 10, Exceptional, (61)
"This is a very nice home. "
Jacksonville Mountain Retreat
Three bedroom with king beds, 2 & a half bathroom. 2146 square foot house.
Fridge, microwave, oven, stovetop

Three bedroom with king beds, 2 & a half bathroom. 2146 square foot house.

9.6 out of 10, Exceptional, (39)
"House was amazing, stayed with family and new grand baby. Everything you could need and the split level was perfect for us! Definitely will rent again next time were in Medford. "
Three bedroom with king beds, 2 & a half bathroom. 2146 square foot house.
Railroad District, steps to downtown, everything you need to enjoy Ashland!
Fridge, microwave, oven, stovetop

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!
Beautiful & Comfortable Home in Central Point
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Beautiful & Comfortable Home in Central Point

10.0 out of 10, Exceptional, (1)
"Clean and comfortable "
The price is €267
includes taxes & fees
18 Feb - 19 Feb
Beautiful & Comfortable Home in Central Point
Pet & family friendly 3bd house, central location, fenced yard.
Fridge, microwave, oven, stovetop

Pet & family friendly 3bd house, central location, fenced yard.

10.0 out of 10, Exceptional, (1)
"Enjoyed the open floor plan. Plenty of space for the entire family and pets. Close to everything in town. We had some issues with the microwave since it kept locking us out and you have to unlug it to get it to open again. Shower was on timer and shot ice cold water with no warning. The backyard has thorny twigs which I had to pull out of my dogs paw. Those are some things that could use some improvements."
Pet & family friendly 3bd house, central location, fenced yard.
Sun Cottage Downtown Jacksonville
Exterior

Sun Cottage Downtown Jacksonville

10.0 out of 10, Exceptional, (15)
"A little noisy with traffic, but the location was perfect. The lighting and ventilation in the kitchen was not the best, but throughout the rest of the house was great. Unfortunately, we burnt a little bit of our dinner and the smoke alarm went on (which was good) but we couldn't turn it off. Otherwise, great place and I would consider returning again."
The price is €311
includes taxes & fees
18 Feb - 19 Feb
Sun Cottage Downtown Jacksonville
Quail Run River View Cottage!
Interior

Quail Run River View Cottage!

10.0 out of 10, Exceptional, (1)
"This house was wonderful and filled all of our needs. Well stocked, very private (behind a gated driveway), and sits on a gorgeous piece of land on the river. Highly recommend! "
Quail Run River View Cottage!
New townhome next to Eagle Point Golf Course, with grill, patio, and WiFi
Fridge, microwave, oven, stovetop

New townhome next to Eagle Point Golf Course, with grill, patio, and WiFi

New townhome next to Eagle Point Golf Course, with grill, patio, and WiFi
The Phoenix House- a place to relax and rejuvenate
Interior

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
Cheerful 3-Bedroom home in Central Point
Miscellaneous

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
The Rellik House and Winery
Deluxe Suite | Living area

The Rellik House and Winery

3.5 star property
9.4 out of 10, Exceptional, (3)
"Beautiful property on the winery. Nicely decorated room & large shower. Separate living, kitchenette & bedroom area. The only downside is the room we had had the parking area on one side & the winery tasting room on the other. So we kept our curtains closed. Also the hot tub was dirty. We were looking forward to using it. "
The price is €320
includes taxes & fees
18 Feb - 19 Feb
The Rellik House and Winery
Charming home, w/hot tub, close to downtown Pet-Friendly!
Outdoor spa tub

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

10.0 out of 10, Exceptional, (34)
"super cool"
The price is €592
includes taxes & fees
21 Feb - 22 Feb
Charming home, w/hot tub, close to downtown Pet-Friendly!
Restful River Retreat
1 bedroom, free WiFi, bed sheets

Restful River Retreat

9.4 out of 10, Exceptional, (24)
"The home was tastefully decorated with holiday seasonal touches that made us feel immediately comfortable and welcomed. The kitchen is well-equipped. The local property manager (Ryan) was extremely helpful, polite, and timely in response. Thank you for a great weekend and we hope to visit again next time we are in the area."
The price is €215
includes taxes & fees
18 Feb - 19 Feb
Restful River Retreat
Tastefully remodeled 3 bedroom 2 bath home with large private back yard
Fridge, microwave, oven, stovetop

Tastefully remodeled 3 bedroom 2 bath home with large private back yard

10.0 out of 10, Exceptional, (37)
"I normally stay in the same house when I drive through Medford in the winter but luckily it was booked and I found this gem! Pet friendly and accommodating owners. Loved the pet stairs for the bed access! So much so that I’m buying a set for myself …. Well for my dog. Thank you "
The price is €384
includes taxes & fees
18 Feb - 19 Feb
Tastefully remodeled 3 bedroom 2 bath home with large private back yard
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

The Rellik House and Winery
Deluxe Suite | Living area

The Rellik House and Winery

3.5 star property
9.4 out of 10, Exceptional, (3)
"Beautiful property on the winery. Nicely decorated room & large shower. Separate living, kitchenette & bedroom area. The only downside is the room we had had the parking area on one side & the winery tasting room on the other. So we kept our curtains closed. Also the hot tub was dirty. We were looking forward to using it. "
The price is €320
includes taxes & fees
18 Feb - 19 Feb
The Rellik House and Winery
Riverfront on the Rogue! Ideal Southern Oregon location
Miscellaneous

Riverfront on the Rogue! Ideal Southern Oregon location

9.8 out of 10, Exceptional, (40)
"The house was perfect for our family Christmas weekend. Plenty of room for all of us. The kitchen and dining area overlooks the Rogue River, beautiful! The house was decorated for Christmas, which was great. Even though it was raining a bit, we enjoyed the fire pit with the kids (& adults) making s'mores and roasting cheese and deli meats. We will definitely keep this place in mind for additional gatherings in the Rogue River area."
Riverfront on the Rogue! Ideal Southern Oregon location
Spacious contemporary home nestled in the foothills of RoxyAnn.
Interior

Spacious contemporary home nestled in the foothills of RoxyAnn.

10.0 out of 10, Exceptional, (15)
"The house was amazing. The host went above and beyond anything we asked and was so accommodating…..very spacious.Quiet neighborhood couldn’t have asked for a better stay!!!!"
Spacious contemporary home nestled in the foothills of RoxyAnn.
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.