Historic Jacksonville Holiday Rentals

    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

Tonight
25 Jul - 26 Jul
Tomorrow
26 Jul - 27 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Holiday Rentals in Historic Jacksonville

Peach Street Inn by WanderLodges
Prepare meals in the fully equipped kitchen with a stainless steel stove, oven, microwave, and spacious countertop.

Peach Street Inn by WanderLodges

2.0 star property
9.0 out of 10, Wonderful, (17)
"Great space to relax, bed was comfy, property was clean and quiet. Awesome spot, would definitely stay again."
Peach Street Inn by WanderLodges
Paschal Winery
Enjoy cooking in this well-equipped kitchen with a large island, sink, and stove.

Paschal Winery

4.5 star property
9.6 out of 10, Exceptional, (10)
"Very nice and hassle free check in "
The price is S$321
includes taxes & fees
4 Aug - 5 Aug
Paschal Winery
A Cowslip's Belle Inn
Relax on the patio surrounded by lush greenery and enjoy the shade of the pergola.

A Cowslip's Belle Inn

3.0 star property
9.8 out of 10, Exceptional, (33)
"Terrific communication with owners, lovely property and close to downtown shops, theatre, etc. Highly recommend!"
The price is S$348
includes taxes & fees
4 Aug - 5 Aug
A Cowslip's Belle Inn
The Rellik House and Winery
Relax in a spacious living area with a comfortable sofa and elegant coffee table.

The Rellik House and Winery

3.5 star property
9.4 out of 10, Exceptional, (3)
"A perfect place to enjoy the winery and countryside! Staff were responsive and friendly!"
The price is S$469
includes taxes & fees
24 Aug - 25 Aug
The Rellik House and Winery
Enchanting Getaway: Farmhouse and Tiny House Duo
Cozy cabin-style accommodation with a compact kitchenette, dining table, and sleeping area.

Enchanting Getaway: Farmhouse and Tiny House Duo

2.0 star property
The price is S$276
includes taxes & fees
5 Aug - 6 Aug
Enchanting Getaway: Farmhouse and Tiny House Duo
Barclay Klum House by WanderLodges
Enjoy meals in this well-lit kitchen with a dining table, oven, and stainless steel sink.

Barclay Klum House by WanderLodges

4.0 star property
10.0 out of 10, Exceptional, (5)
"Great ~ memorable stay. "
The price is S$382
includes taxes & fees
19 Aug - 20 Aug
Barclay Klum House by WanderLodges
Medford Home and 2 Condos With Pool and Hot tub
Relax in this open-plan living space with a kitchen and seating area, featuring a sofa, table, and bar with stools.

Medford Home and 2 Condos With Pool and Hot tub

2.0 star property
The price is S$428
includes taxes & fees
19 Aug - 20 Aug
Medford Home and 2 Condos With Pool and Hot tub
Rogue River Resort
Cabins feature pitched roofs and front porches.

Rogue River Resort

3.0 star property
9.6 out of 10, Exceptional, (37)
"Amazing property and quiet comfortable cabins. "
Rogue River Resort
Hanna's House by WanderLodges
Kitchen equipped with a refrigerator, oven, microwave, and sink, featuring a tiled backsplash.

Hanna's House by WanderLodges

4.0 star property
10.0 out of 10, Exceptional, (1)
"If I were single I could live here. It's that comfortable. The freestanding apartment is ideally located and finished to a very high standard. Amazingly well designed and laid out. Full kitchen, living room, bedroom, and bath. Many, many conveniences. Cafe table in garden outside. We parked once and walked everywhere. Lovely host. Really, I can't imagine anyone giving it less than a perfect score. Would definitely stay here again."
The price is S$256
includes taxes & fees
19 Aug - 20 Aug
Hanna's House by WanderLodges
232 4th Street
Relax in a spacious living room with a sofa, armchairs, and a flat-screen TV.

232 4th Street

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great location with easy access to downtown Ashland. We were able to walk nearly everywhere we wanted to go and enjoyed the neighborhood shops. Overall the neighborhood was quiet and the accommodations were what we wanted. "
232 4th Street
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

Quality Inn & Suites Medford Airport

Quality Inn & Suites Medford Airport

10/10 Excellent
"I had an absolutely wonderful experience during my stay at this hotel. From check-in to check-out, everything was excellent. The staff was warm, welcoming, and attentive to every detail. The room was spotless, comfortable, and well-equipped with everything I needed. I also appreciated the quiet atmosphere and the quality of the amenities. The location was convenient, and the overall ambiance made it a relaxing and enjoyable stay. Whether it was the cleanliness, service, or comfort, every aspect exceeded my expectations. I would highly recommend this hotel to anyone looking for a top-notch stay and will definitely be returning in the future! "
Antonio E. 1-night trip
Posted 18 hours ago
Quality Inn & Suites Medford Airport