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Check prices for these dates

Next weekend
5 Sept - 7 Sept
In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct

Browse Select Historic Jacksonville Holiday Homes

Our top choices for Historic Jacksonville holiday homes

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 £163
includes taxes & fees
26 Aug - 27 Aug
Chateau Herb ~ Miranda Carriage House Apt
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
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
A beautiful Skyfall Landing
Outdoor pool

A beautiful Skyfall Landing

10.0 out of 10, Exceptional, (9)
"We like it because it was nice and quite staying out of the city it was great "
The price is £302
includes taxes & fees
25 Sept - 26 Sept
A beautiful Skyfall Landing
Downtown Ashland House - Walk to Plaza and OSF!
Smart TV, books

Downtown Ashland House - Walk to Plaza and OSF!

9.8 out of 10, Exceptional, (42)
"Perfect location; cute house - enjoyed our stay very much !"
The price is £281
includes taxes & fees
8 Sept - 9 Sept
Downtown Ashland House - Walk to Plaza and OSF!
Riverfront on the Rogue! Ideal Southern Oregon location
Terrace/patio

Riverfront on the Rogue! Ideal Southern Oregon location

9.8 out of 10, Exceptional, (58)
"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
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.
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, (44)
"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.
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
1907 Charmer, Perfect Downtown Location, So Clean!
Outdoor dining

1907 Charmer, Perfect Downtown Location, So Clean!

9.4 out of 10, Exceptional, (119)
"Perfect location for the Shakespeare Festival, very cute house."
1907 Charmer, Perfect Downtown Location, So Clean!
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 £277
includes taxes & fees
15 Sept - 16 Sept
Comfy Cozy Casa
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, (49)
"Perfect style for our family. Ages 3-75 stayed and each person enjoyed themselves! Well equipped for children."
The price is £362
includes taxes & fees
26 Aug - 27 Aug
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
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.

10.0 out of 10, Exceptional, (1)
The price is £215
includes taxes & fees
11 Sept - 12 Sept
This house is a 3 bedroom(s), 2 bathrooms, located in Central Point, OR.
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, (143)
"A very comfortable space with easy access to theaters and restaurants."
Railroad District, steps to downtown, everything you need to enjoy Ashland!
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, (188)
"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!
Jacksonville Place
Fridge, microwave, oven, stovetop

Jacksonville Place

9.0 out of 10, Wonderful, (23)
"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. "
The price is £175
includes taxes & fees
8 Sept - 9 Sept
Jacksonville Place
BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown
Exterior

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

9.6 out of 10, Exceptional, (70)
"Great house within walking distance of downtown shops and restaurants "
BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown
Talent Cottage- 2 King beds, 2 bath with garage!
Terrace/patio

Talent Cottage- 2 King beds, 2 bath with garage!

9.4 out of 10, Exceptional, (12)
"We always enjoy our stay in this cute house. It is well decorated and has everything we need. It’s comfortable and exactly as it is represented on VRBO. Definitely recommend to others!"
The price is £246
includes taxes & fees
26 Aug - 27 Aug
Talent Cottage- 2 King beds, 2 bath with garage!
"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
NEW Downtown Talent Dream
Fridge, microwave, oven, stovetop

NEW Downtown Talent Dream

10.0 out of 10, Exceptional, (9)
"We really enjoyed our time at this property and will absolutely be back. The house was immaculate, had everything we needed and then some... a perfect rental house! Thank you! "
NEW Downtown Talent Dream
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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Top Historic Jacksonville Hotel Reviews

Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

10/10 Excellent
"The beds were comfortable, the room was nice and clean, check in was easy and staff was friendly."
janet 1-night trip
Posted 13 hours ago
Rogue Regency Inn and Suites