Ashland Rentals

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44 Houses

ArtYcottage UNBELIEVEABLE...

Ashland house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“A Place in the Woods to Dream and Live Your Dream” My mouth dropped when I stepped into artYcottage and was surrounded by so much beauty, creativity and originality. It was endless. Everywhere I looked there were remarkable details that were executed with perfection. Rich colors and varied textures everywhere. Everything handmade from the quilts to the furniture to the faucets and tiling and even the soap! One day it was 80 degrees and I enjoyed reading on a chaise on the deck. Then the very next day it was snowing and I was lucky to be there to enjoy the beauty of nature's softness covering the branches of trees. I stayed in that day by the fire my wonderful host, Tom, built. Tom and his stunning and bubbly wife, Margaret, made me feel at home with their warmth and sensitivity. From now on I will definitely be staying here on my twice yearly trips to ashland!

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Price per night from

$225

Cattle View Ranch House

Ashland house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$345

The High Street Cottage An Artists' Garden Cottage

Ashland cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 14 minutes

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Price per night from

$219

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Price per night from

$345

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 14 minutes

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Price per night from

$207

“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!

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Price per night from

$345

Carlisle Garden Suites - Chamomile

Ashland cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$236

Stone's Throw Bungalow - Licensed, Private Garden

Ashland studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$184

Porscha's Hideaway 2

Ashland house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$230

Luxurious Home near Downtown Ashland and Theaters

Ashland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$443

Walk to Downtown/Theaters from this Charming Home

Ashland cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$340

Stay Ashland like never before. Explore days, campfire stars at night!

Ashland caravan/mobile home

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$137

Porscha's Hideaway

Ashland studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$173

Carlisle Garden Suites - Calla Suite

Ashland cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$236

2nd Street Cottages, HERITAGE HOUSE

Ashland cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$569

Nancy's Garden Cottage The Indigo

Ashland cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$144

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$144

Jasmine Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$259

Chamomile Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$259

Carlisle Garden Suites - Pomegranate Suite

Ashland cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$236

Pomegranate Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$259

Carlisle Garden Suites - Daisy Suite

Ashland cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$236

Calla Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$259

Carlisle Garden Suites - Rose Suite

Ashland cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$322

Rose Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$259

Carlisle Garden Suites - Iris Suite

Ashland cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$322

Carlisle Garden Suites - Marigold Suite

Ashland cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$236

Daisy Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$259

Iris Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$259

Carlisle Garden Suites - Jasmine Suite

Ashland cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$236

Marigold Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$259

Carlisle Garden Suites - Viola Suite

Ashland cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$236

Viola Suite at the Carlisle Garden Suites

Ashland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$259

Hargadine House: The Carriage House

Ashland studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$275

Great rentals within 20 miles that match your search

Lotus Studio I

Medford guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$91

Lotus Studio II

Medford guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$114

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

Jacksonville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$229

Mountain Retreat!

Jacksonville house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$914

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rentals in Ashland

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