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Ashland Vacation Rentals

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135 rentals in Ashland.
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ArtYcottage  UNBELIEVEABLE..., vacation rental in Ashland

ArtYcottage UNBELIEVEABLE...

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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8 other travelers have booked this property
De Launay House, vacation rental in Ashland

De Launay House

6 bedrooms
4 bathrooms
Sleeps 14
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Abigail's Two Bedroom Vacation Cottage, easy 10-min. walk to plaza/theaters/shop, vacation rental in Ashland

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

2 bedrooms
2 bathrooms
Sleeps 4
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1 other traveler has booked this property
The High Street Cottage An Artists' Garden Cottage, vacation rental in Ashland

The High Street Cottage An Artists' Garden Cottage

2 bedrooms
1 bathroom
Sleeps 4
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3 other travelers have booked this property
The Terra Cottage Inn a beautiful Luxury Apartment, vacation rental in Ashland

The Terra Cottage Inn a beautiful Luxury Apartment

2 bedrooms
1 bathroom
Sleeps 4
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3 other travelers have booked this property
Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In The Heart Of Ashland, vacation rental in Ashland

Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In The Heart Of Ashland

1 bedroom
1 bathroom
Sleeps 3
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2 other travelers have booked this property
Oberon -Second Spring Property 1-3 Bedroom Luxury, vacation rental in Ashland

Oberon -Second Spring Property 1-3 Bedroom Luxury

1 bedroom
1 bathroom
Sleeps 3
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1 other traveler has booked this property
Perfect vacation cottage, vacation rental in Ashland

Perfect vacation cottage

2 bedrooms
2 bathrooms
Sleeps 6
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1 other traveler has booked this property
Nancy's Garden Cottage The Indigo, vacation rental in Ashland

Nancy's Garden Cottage The Indigo

1 bedroom
1 bathroom
Sleeps 2
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2 other travelers have booked this property
Porscha's Hideaway, vacation rental in Ashland

Porscha's Hideaway

0 bedrooms
1 bathroom
Sleeps 2
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Porscha's Hideaway 2, vacation rental in Ashland

Porscha's Hideaway 2

2 bedrooms
1 bathroom
Sleeps 4
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Stone's Throw Bungalow - Licensed, Private Garden, vacation rental in Ashland

Stone's Throw Bungalow - Licensed, Private Garden

0 bedrooms
1 bathroom
Sleeps 2
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2 other travelers have booked this property
Ashland Lodge Style House w/Patio & 5 MTN Bikes!, vacation rental in Ashland

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

4 bedrooms
3 bathrooms
Sleeps 13
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1 other traveler has booked this property
Luxurious Home near Downtown Ashland and Theaters, vacation rental in Ashland

Luxurious Home near Downtown Ashland and Theaters

3 bedrooms
2 bathrooms
Sleeps 9
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2 other travelers have booked this property
Walk to Downtown/Theaters from this Charming Home, vacation rental in Ashland

Walk to Downtown/Theaters from this Charming Home

2 bedrooms
1 bathroom
Sleeps 6
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1 other traveler has booked this property
Brand New Close to Downtown Small House, vacation rental in Ashland

Brand New Close to Downtown Small House

1 bedroom
1 bathroom
Sleeps 3
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Country setting near Emigrant lake, minutes to downtown Ashland, vacation rental in Ashland

Country setting near Emigrant lake, minutes to downtown Ashland

1 bedroom
1 bathroom
Sleeps 4
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Stacy's 2nd St Cottages .. Steps to theaters and downtown Ashland, vacation rental in Ashland

Stacy's 2nd St Cottages .. Steps to theaters and downtown Ashland

2 bedrooms
1 bathroom
Sleeps 4
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Classic Victorian- Sleeps 8...a Short Stroll to the Theatres, vacation rental in Ashland

Classic Victorian- Sleeps 8...a Short Stroll to the Theatres

3 bedrooms
3 bathrooms
Sleeps 8
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Beautiful little place. Walk to town and theaters!, vacation rental in Ashland

Beautiful little place. Walk to town and theaters!

2 bedrooms
1 bathroom
Sleeps 4
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Beautiful Historical Home 2 Blocks from Theater and Plaza!, vacation rental in Ashland

Beautiful Historical Home 2 Blocks from Theater and Plaza!

2 bedrooms
1 bathroom
Sleeps 6
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Hanna's House- Your Home Away from Home, vacation rental in Ashland

Hanna's House- Your Home Away from Home

1 bedroom
1 bathroom
Sleeps 3
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Charming, Comfortable Garden Studio Above The University., vacation rental in Ashland

Charming, Comfortable Garden Studio Above The University.

1 bedroom
1 bathroom
Sleeps 3
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The Ashland Cottage, walk to town, vacation rental in Ashland

The Ashland Cottage, walk to town

1 bedroom
2 bathrooms
Sleeps 4
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The Brenden House, Walk to Theaters, vacation rental in Ashland

The Brenden House, Walk to Theaters

3 bedrooms
3 bathrooms
Sleeps 8
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The Dogwood Suite at Tudor House Vacation Rentals, vacation rental in Ashland

The Dogwood Suite at Tudor House Vacation Rentals

1 bedroom
2 bathrooms
Sleeps 5
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Craftsman Style Home In Country Setting, vacation rental in Ashland

Craftsman Style Home In Country Setting

4 bedrooms
3 bathrooms
Sleeps 10
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~AGC~ Oberon 4 Blocks 2 Downtown - Charming Cozy Private Stylish Shakespeare OSF, vacation rental in Ashland

~AGC~ Oberon 4 Blocks 2 Downtown - Charming Cozy Private Stylish Shakespeare OSF

1 bedroom
1 bathroom
Sleeps 2
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Private Suite Near Shakespeare, vacation rental in Ashland

Private Suite Near Shakespeare

1 bedroom
1 bathroom
Sleeps 2
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The Maple Apartment at Tudor House Vacation Rentals, vacation rental in Ashland

The Maple Apartment at Tudor House Vacation Rentals

2 bedrooms
2 bathrooms
Sleeps 6
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Cattle View Ranch House, vacation rental in Ashland

Cattle View Ranch House

4 bedrooms
2 bathrooms
Sleeps 9
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Beautiful Apartment in Ashland, vacation rental in Ashland

Beautiful Apartment in Ashland

1 bedroom
1 bathroom
Sleeps 2
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The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean, vacation rental in Ashland

The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean

3 bedrooms
2 bathrooms
Sleeps 10
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2nd Street Cottages, GARDEN SUITE, vacation rental in Ashland

2nd Street Cottages, GARDEN SUITE

2 bedrooms
2 bathrooms
Sleeps 5
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1 other traveler has booked this property
2nd Street Cottages, HERITAGE HOUSE, vacation rental in Ashland

2nd Street Cottages, HERITAGE HOUSE

4 bedrooms
3 bathrooms
Sleeps 8
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Carlisle Garden Suites - Calla Suite, vacation rental in Ashland

Carlisle Garden Suites - Calla Suite

1 bedroom
1 bathroom
Sleeps 2
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Carlisle Garden Suites - Jasmine Suite, vacation rental in Ashland

Carlisle Garden Suites - Jasmine Suite

1 bedroom
1 bathroom
Sleeps 2
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Carlisle Garden Suites - Viola Suite, vacation rental in Ashland

Carlisle Garden Suites - Viola Suite

1 bedroom
1 bathroom
Sleeps 2
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Carlisle Garden Suites - Pomegranate Suite, vacation rental in Ashland

Carlisle Garden Suites - Pomegranate Suite

1 bedroom
1 bathroom
Sleeps 2
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Carlisle Garden Suites - Rose Suite, vacation rental in Ashland

Carlisle Garden Suites - Rose Suite

1 bedroom
1 bathroom
Sleeps 3
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Carlisle Garden Suites - Iris Suite, vacation rental in Ashland

Carlisle Garden Suites - Iris Suite

1 bedroom
1 bathroom
Sleeps 3
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Carlisle Garden Suites - Marigold Suite, vacation rental in Ashland

Carlisle Garden Suites - Marigold Suite

1 bedroom
1 bathroom
Sleeps 3
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Carlisle Garden Suites - Daisy Suite, vacation rental in Ashland

Carlisle Garden Suites - Daisy Suite

1 bedroom
1 bathroom
Sleeps 2
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Carlisle Garden Suites - Chamomile, vacation rental in Ashland

Carlisle Garden Suites - Chamomile

1 bedroom
1 bathroom
Sleeps 2
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1 other traveler has booked this property
Stay Ashland like never before.  Explore days, campfire stars at night!, vacation rental in Ashland

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

1 bedroom
1 bathroom
Sleeps 3
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Water Suite with Terrace, vacation rental in Ashland

Water Suite with Terrace

1 bedroom
1 bathroom
Sleeps 2
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Pelton Villa, vacation rental in Ashland

Pelton Villa

4 bedrooms
3 bathrooms
Sleeps 8
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Earth King Suite with Jacuzzi, vacation rental in Ashland

Earth King Suite with Jacuzzi

1 bedroom
1 bathroom
Sleeps 3
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Emigrant Creek Guest Lodge on the East Side of Emigrant Lake, 8 miles to Ashland, vacation rental in Ashland

Emigrant Creek Guest Lodge on the East Side of Emigrant Lake, 8 miles to Ashland

2 bedrooms
2 bathrooms
Sleeps 4
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Chamomile Suite at the Carlisle Garden Suites, vacation rental in Ashland

Chamomile Suite at the Carlisle Garden Suites

1 bedroom
1 bathroom
Sleeps 2
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Ashland Vacation Rentals
Are you looking for the perfect vacation rental in Ashland, Ore.? Then come on in and take a look. Ashland, noted for its postcard picture perfect seasons, beautiful topography and friendly people, is the perfect vacation spot. Now that you’ve found it, you need someplace to stay. Rental cabins are a wonderful option and may be ideal for you and your family. Many are only a hop, skip and a jump from Ashland amenities, while affording you the privacy you desire. Make it a vacation to remember with a rental cottage, condo or cabin. With multiple price points and rental options, you’re sure to find something that fits your budget – and we can help.
More
Ashland Vacation Rentals
Are you looking for the perfect vacation rental in Ashland, Ore.? Then come on in and take a look. Ashland, noted for its postcard picture perfect seasons, beautiful topography and friendly people, is the perfect vacation spot. Now that you’ve found it, you need someplace to stay. Rental cabins are a wonderful option and may be ideal for you and your family. Many are only a hop, skip and a jump from Ashland amenities, while affording you the privacy you desire. Make it a vacation to remember with a rental cottage, condo or cabin. With multiple price points and rental options, you’re sure to find something that fits your budget – and we can help.
Ashland Activities
If you’re looking for something to do while you’re in Ashland, head on over to the Oregon Shakespeare Festival. Each season brings something different for Shakespeare lovers ranging from tours to your favorite play. Other cultural events include the Oregon Cabaret Theater and the Ashland Independent Film Festival. Ashland is also home to more than 80 art galleries and multiple museums, such as the ScienceWorks Hands On Museum for children and the Ashland Art Center. From your home away from home vacation rental, plan your day around the activities that suit you best!
Romancing Ashland
Of course, with its beautiful location at the base of the Cascade Mountain Range, Ashland is perfect for lovers. Let us help you find a quaint rental cottage for two, while you focus on romance! Wine and dine with the best of them at several area restaurants including Chateaulin French restaurant. Here, you’ll find the perfect ambiance in the intimate and romantic dining room as well as an extensive wine list and gourmet French food. Or try the nationally acclaimed Winchester Restaurant at the Winchester Inn. Take your chocolate loving sweetie to the Oregon Chocolate Festival or go for a bike ride on the Mt. Ashland Mountain Bike Trail.
Ashland is for Skiing and Golf
With several mountain ranges in the Southern Oregon area, Ashland is perfect for the ski enthusiast! Hit the slopes at any one of the area resorts with trails ranging from beginner to professional, cross country to downhill. Find a rental cabin with access just outside your door and you’ll be in ski heaven. Located at 7,500 feet, Mt. Ashland offers skiing during the season from November to April on a variety of trails for any skill level as well as snowboarding. Golf resorts include Oak Knoll in Ashland and Centennial Golf Club in nearby Medford.