Holiday Homes in Historic Jacksonville

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Featured Holiday Homes in Historic Jacksonville

Jacksonville Place
Fridge, microwave, oven, stovetop

Jacksonville Place

9.0 out of 10, Wonderful, (26)
"It was a nice quiet place, wish I could’ve stayed longer. "
The price is NZ$327
includes taxes & fees
5 Oct - 6 Oct
Jacksonville Place
Jacksonville Mountain Retreat
Exterior detail

Jacksonville Mountain Retreat

9.8 out of 10, Exceptional, (75)
"We loved our stay at the property! The house and pool and hot tub were all wonderful! Easy access to many activities and restaurants. The driveway is a steep hill and the property lacks a yard for kids to play in, but everything else made up for that."
Jacksonville Mountain Retreat
Small house perfect for families and pets
Fridge, oven, dishwasher

Small house perfect for families and pets

8.8 out of 10, Excellent, (22)
"We were in town for a family gathering. The location was great, and the apartment was clean and fully stocked with essentials."
The price is NZ$406
includes taxes & fees
4 Oct - 5 Oct
Small house perfect for families and pets
3 bedrooms with king beds, 2 1/2 bathrooms. 2146 sq ft house in east Medford.
Fridge, microwave, oven, stovetop

3 bedrooms with king beds, 2 1/2 bathrooms. 2146 sq ft house in east Medford.

9.6 out of 10, Exceptional, (46)
"A great place for a family getaway. Lots of room, loved all king beds, truly enjoyed the home."
3 bedrooms with king beds, 2 1/2 bathrooms. 2146 sq ft house in east Medford.
Off-grid tiny home on 6 secluded acres w/ outdoor soaking tubs and sauna!
Property grounds

Off-grid tiny home on 6 secluded acres w/ outdoor soaking tubs and sauna!

9.6 out of 10, Exceptional, (10)
"An amazing place to stay that is off grid and quiet for a great vacation!! "
Off-grid tiny home on 6 secluded acres w/ outdoor soaking tubs and sauna!
Chateau Herb ~ Miranda Carriage House Apt
Outdoor spa tub

Chateau Herb ~ Miranda Carriage House Apt

9.6 out of 10, Exceptional, (4)
"Nice place to stay, with full kitchen, and a close drive to downtown Ashland. The AC stopped and the staff were very responsive and provided."
The price is NZ$408
includes taxes & fees
5 Oct - 6 Oct
Chateau Herb ~ Miranda Carriage House Apt
Pet & family friendly 3bd house, central location, fenced yard.
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (7)
"Great place, plenty of space for family and fur babies. Centralized location. Would definitely stay here again "
Pet & family friendly 3bd house, central location, fenced yard.
BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown
Terrace/patio

BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown

9.6 out of 10, Exceptional, (86)
"This house is cute and clean. The check-in process was easy and smooth and we had everything we needed for a comfortable stay. It is about 12 blocks to the theater...about a 15 minute walk, so fairly convenient."
BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown
Great, clean house in the middle of Medford
Fridge, microwave, oven, stovetop

Great, clean house in the middle of Medford

9.2 out of 10, Wonderful, (52)
"The house was very clean. It is located in a central location near all interesting sights. We would definitely stay here again."
The price is NZ$526
includes taxes & fees
12 Oct - 13 Oct
Great, clean house in the middle of Medford
New Downtown 3 Bedroom Upstairs Flat with views
Fridge, microwave, oven, stovetop

New Downtown 3 Bedroom Upstairs Flat with views

9.8 out of 10, Exceptional, (31)
"This is our second year staying here for a girl's weekend! It's a great location and a cozy environment to have a chill morning before the plays. The host responded to our needs and we were very happy! We'll probably stay here next year too!"
New Downtown 3 Bedroom Upstairs Flat with views
California Cottage: Downtown!
Fridge, microwave, stovetop, dishwasher

California Cottage: Downtown!

9.8 out of 10, Exceptional, (36)
"The interior of the cottage was wonderful. The exterior was somewhat of a construction site."
The price is NZ$393
includes taxes & fees
5 Oct - 6 Oct
California Cottage: Downtown!
Sun Cottage Downtown Jacksonville
Exterior

Sun Cottage Downtown Jacksonville

10.0 out of 10, Exceptional, (24)
"This cottage is in a great location, right in the center of Jacksonville, OR!"
Sun Cottage Downtown Jacksonville
Historic Farm Estate | Fairytale Haven | Ashland
Fridge, microwave, oven, stovetop

Historic Farm Estate | Fairytale Haven | Ashland

9.0 out of 10, Wonderful, (7)
"Beautiful property. Great communication and easy check-in. "
Historic Farm Estate | Fairytale Haven | Ashland
Red Barn in Wine Country
Property grounds

Red Barn in Wine Country

9.8 out of 10, Exceptional, (7)
"We had an amazing time and really enjoyed the property. Enjoyed the bounty of the garden with our bbq night. Our host was very kind and made sure we felt welcome. Highly recommend for a nice visit away from the city. "
The price is NZ$478
includes taxes & fees
5 Oct - 6 Oct
Red Barn in Wine Country
East Main Downtown Bungalow
Microwave, dishwasher

East Main Downtown Bungalow

9.2 out of 10, Wonderful, (38)
"Great spot for those looking to visit for the Shakespeare festival - walking distance from everything! Really nice place to stay - felt super comfortable there. "
The price is NZ$441
includes taxes & fees
5 Oct - 6 Oct
East Main Downtown Bungalow
The Mountain Ave House by WanderLodges
Grand House | Private kitchen

The Mountain Ave House by WanderLodges

4.0 star property
10.0 out of 10, Exceptional, (7)
"Lovely space and very comfortable; walkable from downtown "
The price is NZ$845
includes taxes & fees
2 Nov - 3 Nov
The Mountain Ave House by WanderLodges
BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown
Exterior

BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown

9.8 out of 10, Exceptional, (71)
"Great house within walking distance of downtown shops and restaurants "
BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown
"Enchantment" Medford, Oregon
Outdoor dining

"Enchantment" Medford, Oregon

9.8 out of 10, Exceptional, (37)
"The fairies that live there are very active."
"Enchantment" Medford, Oregon
Whether you're here to explore the Rogue River, Crater Lake, or the Britt Festival, this location is the perfect home base for your Southern Oregon experience!
Fridge, microwave, oven, stovetop

Whether you're here to explore the Rogue River, Crater Lake, or the Britt Festival, this location is the perfect home base for your Southern Oregon experience!

10.0 out of 10, Exceptional, (1)
The price is NZ$489
includes taxes & fees
6 Oct - 7 Oct
Whether you're here to explore the Rogue River, Crater Lake, or the Britt Festival, this location is the perfect home base for your Southern Oregon experience!
Charming white picket fenced home in quiet area
Living area

Charming white picket fenced home in quiet area

10.0 out of 10, Exceptional, (12)
"Great home and hosts are very understanding with out checkout time. Would book with them again. My whole family enjoyed the stay. Very safe neighborhood ."
Charming white picket fenced home in quiet area
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Historic Jacksonville Hotel Reviews

Flagship Inn of Ashland

Flagship Inn of Ashland

10/10 Excellent
"Excellent, especially for the price. The bed was super comfy, and the room was well-appointed and nicely decorated. We will return and tell our friends about Flagship."
Delena 1-night trip
Posted 2 days ago
Flagship Inn of Ashland

Find out more about Historic Jacksonville

Find out more about Historic Jacksonville

Historic Jacksonville Holiday Homes information

Number of reviews
583
Accommodation
235 Holiday Homes
Lowest Price
NZ$327
Highest Price
NZ$845

Explore a world of travel with Expedia

Explore a world of travel with Expedia