Holiday Homes in Historic Jacksonville

    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

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Historic Jacksonville and around

Our top choices for Historic Jacksonville holiday homes

East Main Downtown Bungalow
Microwave, dishwasher

East Main Downtown Bungalow

9.2 out of 10, Wonderful, (33)
"Great location and the space was extremely functional and well thought out!"
East Main Downtown Bungalow
A beautiful Skyfall Landing
Outdoor pool

A beautiful Skyfall Landing

10.0 out of 10, Exceptional, (9)
"The home is clean, comfortable, and spacious. The bedrooms are a great size, beds are comfortable and rooms are private. Very easy access private drive up. Peaceful backyard view and a few steps to the salt water pool and hot tub. Fishing, hunting, or just relaxing we will stay again..."
The price is €384
includes taxes & fees
1 Sept - 2 Sept
A beautiful Skyfall Landing
Riverfront on the Rogue! Ideal Southern Oregon location
Terrace/patio

Riverfront on the Rogue! Ideal Southern Oregon location

9.8 out of 10, Exceptional, (57)
"This place was perfect for our family of 6. Everyone had their own space and it is conveniently located. Clean, welcoming and super cute!"
Riverfront on the Rogue! Ideal Southern Oregon location
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, (79)
"The cottage was clean, comfortable, and very well situated in town. The kitchen was well equipped, allowing us to cook most of our meals there. It's in a quiet neighborhood where you can walk to anything you might want."
BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown
Entertainment Home on Golf Course - Hot Tub /Pool
Outdoor dining

Entertainment Home on Golf Course - Hot Tub /Pool

10.0 out of 10, Exceptional, (8)
"We had an amazing time. The property is beautiful and the hosts are very responsive and easy to work with. The house is so amazing, you won’t want to leave."
Entertainment Home on Golf Course - Hot Tub /Pool
Comfy Cozy Casa
Interior

Comfy Cozy Casa

10.0 out of 10, Exceptional, (52)
"We had a great experience at this property and it was close in proximity to an event that we attended."
The price is €418
includes taxes & fees
19 Sept - 20 Sept
Comfy Cozy Casa
New Downtown 3 Bedroom Upstairs Flat with views
Fridge, microwave, oven, stovetop

New Downtown 3 Bedroom Upstairs Flat with views

9.6 out of 10, Exceptional, (29)
"We have now stayed Amber‘s place five or six times and each time it has been delightful. It is in a convenient location, the deck has a fabulous view, we always have a quick response for anything we need. We are already looking forward to our next visit."
New Downtown 3 Bedroom Upstairs Flat with views
Winchester family home
Terrace/patio

Winchester family home

9.2 out of 10, Wonderful, (25)
"The place was clean and a lovley place to stay "
Winchester family home
1 king bed 1 queen bed 2 bedroom house with AC, WiFi and washer and dryer
Exterior

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, (14)
"Clean quiet comfortable"
The price is €297
includes taxes & fees
19 Sept - 20 Sept
1 king bed 1 queen bed 2 bedroom house with AC, WiFi and washer and dryer
This house is a 3 bedroom(s), 2 bathrooms, located in Central Point, OR.
Fridge, microwave, oven, stovetop

This house is a 3 bedroom(s), 2 bathrooms, located in Central Point, OR.

The price is €245
includes taxes & fees
11 Sept - 12 Sept
This house is a 3 bedroom(s), 2 bathrooms, located in Central Point, OR.
The Fairway Townhouse | Minutes from Golf Course | Sleeps Up To 7
Fridge, microwave, oven, stovetop

The Fairway Townhouse | Minutes from Golf Course | Sleeps Up To 7

The Fairway Townhouse | Minutes from Golf Course | Sleeps Up To 7
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Outdoor spa tub

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

10.0 out of 10, Exceptional, (48)
"Very charming home with everything you need to relax and enjoy a vacation in Ashland, Oregon."
The price is €528
includes taxes & fees
19 Sept - 20 Sept
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
In the historic railroad district, walking distance to all the best of Ashland!
Outdoor dining

In the historic railroad district, walking distance to all the best of Ashland!

10.0 out of 10, Exceptional, (187)
"We thoroughly enjoyed our stay in the house with easy access to everything in the theater district! The house is comfortable and well stocked. We'll be back!"
In the historic railroad district, walking distance to all the best of Ashland!
The River House with Views of the Famous Rogue River! No cleaning fees!
Exterior

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

9.6 out of 10, Exceptional, (36)
"House was amazing and we enjoyed are stay."
The River House with Views of the Famous Rogue River! No cleaning fees!
Jacksonville Place
Fridge, microwave, oven, stovetop

Jacksonville Place

9.0 out of 10, Wonderful, (22)
"We enjoyed our stay here. When we first arrived, the cleaning staff was on their way. We left for dinner and came back to a clean house. We had what we needed for the 3 nights we were in town and plenty of room for me, my husband, three daughters and my mom. Fair price and decent place to stay. I’m sure we would stay here again if we come back through this area. "
Jacksonville Place
"Enchantment" Medford, Oregon
Outdoor dining

"Enchantment" Medford, Oregon

9.8 out of 10, Exceptional, (37)
"Carol was amazing and we enjoyed our stay here! Very responsive and clean. Highly recommend staying here!"
"Enchantment" Medford, Oregon
Station House Suite B~Downtown Jacksonville~Rooftop Patio~Walking Distance to Britt!
Property grounds

Station House Suite B~Downtown Jacksonville~Rooftop Patio~Walking Distance to Britt!

10.0 out of 10, Exceptional, (5)
"Great memories made here! The space was nicely decorated, it was clean, modern, and well equipped."
Station House Suite B~Downtown Jacksonville~Rooftop Patio~Walking Distance to Britt!
BF Dowell House
Exterior

BF Dowell House

9.8 out of 10, Exceptional, (64)
"We invited 3 long time couple friends to come visit us in Jacksonville. They stayed in the BF Dowell House and loved it. They wanted to make sure I left a good review because they were so impressed with how clean and well organized it was. They yard was so lovely too. We definitely recommend it!!"
BF Dowell House
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, (57)
"Great location - close to restaurants and shops! "
Premier Downstairs Flat in Perfect Down Town Location
Spacious Grants Pass Home w/ Hot Tub & River Views
Fridge, microwave, stovetop, dishwasher

Spacious Grants Pass Home w/ Hot Tub & River Views

9.6 out of 10, Exceptional, (27)
"We loved the property. The house was impeccably clean. "
Spacious Grants Pass Home w/ Hot Tub & River Views
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.
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
"It was quiet, nicely appointed, loved the Kuerig coffee appliance."
Carolyn 1-night trip
Posted 1 day ago
Flagship Inn of Ashland