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Ashland Rentals

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113 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!

Responds fast! avg. 3 hours 25 minutes

Price per night from

$203

Ashland Cabin - 170 Acres w/Mountain Views & Sauna

Ashland cottage

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 6 minutes

Price per night from

$145

Cattle View Ranch House

Ashland house

4 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$347

Price per night from

$347

The High Street Cottage An Artists' Garden Cottage

Ashland cottage

2 bedrooms / 1 bathroom / sleeps 4

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.

Price per night from

$185

Stone's Throw Bungalow - Licensed, Private Garden

Ashland studio

Studio / 1 bathroom / sleeps 2

Price per night from

$156

Walk to Downtown/Theaters from this Charming Home

Ashland cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$342

Oberon -Second Spring Property 1-3 Bedroom Luxury

Ashland apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$226

Farmhouse Studio at Willow Witt Ranch

Ashland house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$232

Luxurious Home near Downtown Ashland and Theaters

Ashland house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$441

Meadow House on a Historic Ranch in Ashland, OR

Ashland house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$341

Ashland Lodge Style House w/Patio & 5 MTN Bikes!

Ashland house

4 bedrooms / 3 bathrooms / sleeps 13

Responds fast! avg. 6 minutes

Price per night from

$350

Porscha's Hideaway 2

Ashland house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$232

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

$214

Carlisle Garden Suites - Chamomile

Ashland cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$237

2nd Street Cottages, GARDEN SUITE

Ashland cottage

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$342

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

Ashland caravan/mobile home

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$138

Carlisle Garden Suites - Calla Suite

Ashland cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$237

Blue Moon House & Cottage ~ Just 5 Blocks from OSF

Ashland house

7 bedrooms / 6 bathrooms / sleeps 15

Price per night from

$294

2nd Street Cottages, HERITAGE HOUSE

Ashland cottage

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$481

#52 The Cabins at Hyatt Lake - Sleeps 4 -Lake View - Hot Tub

Ashland chalet

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$117

The Pioneer House (North Suite) - Closest to OSF!

Ashland house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$205

Perfect vacation cottage

Ashland cottage

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$330

Pelton Villa

Ashland house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$376

#33 The Cabins at Hyatt Lake - Sleeps 6 - Hot Tub

Ashland chalet

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$148

Porscha's Hideaway

Ashland studio

Studio / 1 bathroom / sleeps 2

Price per night from

$174

Steps to theatres, shopping, dining, nightlife...

Ashland house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$486

Nancy's Garden Cottage The Indigo

Ashland cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$52

Carlisle Garden Suites - Pomegranate Suite

Ashland cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$237

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

Ashland house

7 bedrooms / 6 bathrooms / sleeps 13

Price per night from

$412

#44 The Cabins at Hyatt Lake - Sleeps 6 - Hot Tub

Ashland chalet

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$148

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

Ashland house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$206

The Pioneer - Craftsman House - Closest to OSF!

Ashland house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$177

Carlisle Garden Suites - Daisy Suite

Ashland cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$237

Price per night from

$145

Carlisle Garden Suites - Rose Suite

Ashland cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$324

Jasmine Suite at the Carlisle Garden Suites

Ashland apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$261

Viewing 38 of 113
rentals in Ashland

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Top Destination reviews

Affordable, Private Retreat for 2 with Great Views
Private, quiet, comfortable retreat with great views just minute

The perfect place for our ashland retreat. Quiet rural location but just a few minutes drive from town. The loft apartment is comfortable, very private and - the best part - has an amazing large deck to the side away from the owners, with great views, loungers, dining set & grille. We have stayed in several vacation rentals in ashland, but consider this a great find suiting our needs for both peaceful comfort as well as convenience to theaters, shops & restaurants. Thank you to Marty & Michael for creating this perfect haven and for being such gracious hosts. We will return.see more
ArtYcottage UNBELIEVEABLE...
Most beautiful spot in ashland

We stayed at artYcottage while visiting friends in ashland recently and were so impressed. Everything in the private cottage is made by the owners and it's all exquisite! The owners were wonderfully welcoming and very knowledgeable about things to do in ashland. We spent every evening on our private deck watching the local deer. The cottage is outside of ashland set among oak trees so it was quiet and very private. We had a wonderful time and have already booked our next stay!see more
Abigail's Two Bedroom Vacation Cottage, easy 10-min. walk to plaza/theaters/shop
bright, comfortable, nicely appointed, excellent home-cooked bre

We stayed in the Cottage for two nights with our small dog during a holiday visit to ashland for the Shakespeare festival. The cottage is roomy, clean, comfortable, very well equipped and attractively decorated. We particularly appreciated having breakfast delivered on a tray. Breakfast was excellent, with juice, pastry, fruit and yogurt, as well as perfectly cooked scrambled eggs with cheese one day and chocolate chip pancakes the next. Abi and Patti were friendly and welcoming. We're definitely planning to be back.see more
De Launay House
Amazing Details!

Delaunay House is a special place in an area that offers so much to those that travel. This romantic historic home welcomes you in and swallows your stress. The attention to details and the warmth of the proprietor immediately make you feel 'home'. Original art, victorian furniture, giant wrap around porch complete with rocking chairs will bring me back again and again!see more
The Pioneer - Craftsman House - Closest to OSF!
Loved the house and the location.

We stayed at the Pioneer house for 4 night and loved it. We saw two plays while we were there and the location was excellent. Will definitely rent the house again. … see more
The Terra Cottage Inn a beautiful Luxury Apartment
Perfect!! Will go back!

What a lovely place to stay and enjoy some relaxing time in a very comfortable setting. Elizabeth and Mark Schoenleber were such gracious hosts. They take such pride in their home and they are very accommodating to their guests. If you are looking for a place to stay while in the town of Ashland, to see the plays or just get away from it all, they are definitely the place to stay. The apartment that we stayed in was so nice. They had everything you could imagine you'd ever need and then some! Thanks so much again for letting us enjoy your little world. You're the best.see more

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