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Jacksonville Rentals

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93 Results

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Price: high to low

Number of reviews

93 Houses

Beautiful Luxury Cottage "The Quarters" - Walk to it All !

Jacksonville house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$228

Private Entrance. Relaxed Luxury

Jacksonville b&b

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 48 minutes

Price per night from

$114

Mountainview. Relaxed Luxury

Jacksonville b&b

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 48 minutes

Price per night from

$102

The Lily Pad

Jacksonville house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$286

The Tiger's Den- Tiger Lily Inn

Jacksonville cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$286

Raven Suite at Rellik ~ Winery & Alpaca Farm ~ POOL~ One Mile to Jacksonville

Jacksonville house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 15 minutes

Price per night from

$148

Wine Suite at Rellik House~POOL~ Winery & Alpaca Farm ~ One Mile to Jacksonville

Jacksonville house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 15 minutes

Price per night from

$148

Alpaca Suite at Rellik ~ Winery & Alpaca Farm ~ POOL~ One Mile to Jacksonville

Jacksonville house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 15 minutes

Price per night from

$148

Rellik House~Pool~ Winery and Alpaca Farm ~ One Mile to Jacksonville

Jacksonville house

6 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 15 minutes

Price per night from

$471

Great rentals within 20 miles that match your search

Oberon -Second Spring Property 1-3 Bedroom Luxury

Ashland apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$224

Price per night from

$344

The High Street Cottage An Artists' Garden Cottage

Ashland cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 34 minutes

Price per night from

$189

The Terra Cottage Inn a beautiful Luxury Apartment

Ashland cottage

2 bedrooms / 1 bathroom / sleeps 4

“Perfect!” We just returned from our annual trip to ashland, mainly for OSF. After previously staying in B&B;'s we chose to find a rental house for this week. I did a bunch of research and what struck us about the Terra Cottage Inn was the outdoor kitchen. Since my wife I like to cook, we though this would be the place. I will say this is one place where the pictures do not do the property justice. First, the outdoor kitchen: it is the best! The grill, the stove, the sink, the refrigerator, the incredible clay pottery that one of the proprietors (Elizabeth) and the table and benches that the other proprietor (Mark) made make it a perfect spot. We took advantage of this spot to have several dinners and with the lounge chairs, it is perfect for morning coffee.It should be noted that the Terra Cottage Inn is part of a beautiful property that includes one other rental house and the owners house. Besides the outdoor kitchen, there is a Koi pond, a garden (from which you can pick anything from), a hammock, and outdoor shower (if you want to use it) and Elizabeth's Pottery Studio and Mark's art Studios. The have decorated the whole property with great lights and artistic touches everywhere. Terra Cottage Inn is in it's own building up a flight stairs(nothing but storage down below). It is not large, but perfect for a vacation rental. During our visit the temps in ashland were above 100 degrees, but the air conditioning kept is nice and cool. The kitchen is well stocked and the living room furniture is very comfortable.The linens in the bedroom are great and the queen bed is comfortable. They also provide great bathrobes! There is a second bedroom with two twin beds (which we didn't need to use). Bathroom has good water pressure and they provided almost everything you could need (shampoo, soap. lotion etc...). The inside space is not huge, but very comfortable, when you add in all the magical outdoor areas this is an a+ space and we will be back every year.

Responds fast! avg. 2 hours 34 minutes

Price per night from

$184

Abigail's Two Bedroom Vacation Cottage, easy 10-min. walk to plaza/theaters/shop

Ashland cottage

2 bedrooms / 2 bathrooms / sleeps 4

“Fabulous place to stay!” We recently stayed in this cottage for 3 nights and we really enjoyed ourselves. The short walk to the plaza and theaters was ideal, but we were most impressed by how clean and well-maintained the cottage was. The cottage is on the property of the Hersey House Bed and Breakfast Inn and the hosts were very welcoming, and they deliver a morning continental breakfast tray. We especially liked the warm raspberry crumble with sweet cream and it was nice because we enjoyed 3 breakfast trays and each morning we were served something different. We really like the cottage and it was super easy with our kids because there were two bedrooms and it was handy to have the kitchen. We will definitely be back!

Price per night from

$212

Perfect vacation cottage

Ashland cottage

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$327

Nancy's Garden Cottage The Indigo

Ashland cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 43 minutes

Price per night from

$144

Luxurious Home near Downtown Ashland and Theaters

Ashland house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$441

Walk to Downtown/Theaters from this Charming Home

Ashland cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$338

2nd Street Cottages, GARDEN SUITE

Ashland cottage

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$338

2nd Street Cottages, HERITAGE HOUSE

Ashland cottage

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$481

Guest room with private bath in a Cozy Log Cabin!

Talent private room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$67

Paschal Winery Dream Cottage 1 ~ Hot Tub

Talent villa

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 15 minutes

Price per night from

$148

RedTail ~ McCall Suite~Tesla Station~ 4 Blocks to OSF!

Ashland house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 15 minutes

Price per night from

$171

The Pioneer - Craftsman House - Closest to OSF!

Ashland house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 15 minutes

Price per night from

$177

The Pioneer House - South Suite (Downstairs) - Closest to OSF!

Ashland house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 15 minutes

Price per night from

$171

Anne Hathaway's House ~ Just 4 blocks from OSF!~ Kitchen

Ashland house

7 bedrooms / 6 bathrooms / sleeps 13

Responds fast! avg. 15 minutes

Price per night from

$413

Carlisle Garden Suites - Calla Suite

Ashland cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$235

Carlisle Garden Suites - Chamomile

Ashland cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$235

Carlisle Garden Suites - Daisy Suite

Ashland cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$235

Carlisle Garden Suites - Jasmine Suite

Ashland cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$235

Carlisle Garden Suites - Marigold Suite

Ashland cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$235

Carlisle Garden Suites - Rose Suite

Ashland cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$321

Carlisle Garden Suites - Pomegranate Suite

Ashland cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$235

Carlisle Garden Suites - Viola Suite

Ashland cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$235

Carlisle Garden Suites - Iris Suite

Ashland cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$321

Calla Suite at the Carlisle Garden Suites

Ashland apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$258

Chamomile Suite at the Carlisle Garden Suites

Ashland apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$258

Daisy Suite at the Carlisle Garden Suites

Ashland apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$258

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