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Ashland Cottages

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0 rentals in Ashland.
The Ashland Cottage, walk to town, vacation rental in Ashland
The Ashland Cottage, walk to town, vacation rental in Ashland
The Ashland Cottage, walk to town, vacation rental in Ashland

The Ashland Cottage, walk to town

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Craftsman Style Home in Country Setting, vacation rental in Ashland
Craftsman Style Home in Country Setting, vacation rental in Ashland
Craftsman Style Home in Country Setting, vacation rental in Ashland

Craftsman Style Home in Country Setting

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Asian Inspired Escape with View - Just 3 Miles from Downtown, vacation rental in Ashland
Asian Inspired Escape with View - Just 3 Miles from Downtown, vacation rental in Ashland
Asian Inspired Escape with View - Just 3 Miles from Downtown, vacation rental in Ashland

Asian Inspired Escape with View - Just 3 Miles from Downtown

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Hanna's House- Your Home Away from Home, vacation rental in Ashland
Hanna's House- Your Home Away from Home, vacation rental in Ashland
Hanna's House- Your Home Away from Home, vacation rental in Ashland

Hanna's House- Your Home Away from Home

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Railroad District, steps to downtown, everything you need to enjoy Ashland!, vacation rental in Ashland
Railroad District, steps to downtown, everything you need to enjoy Ashland!, vacation rental in Ashland
Railroad District, steps to downtown, everything you need to enjoy Ashland!, vacation rental in Ashland

Railroad District, steps to downtown, everything you need to enjoy Ashland!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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High Street Cottage Artists' Garden Cottage Clean & Beautiful, vacation rental in Ashland
High Street Cottage Artists' Garden Cottage Clean & Beautiful, vacation rental in Ashland
High Street Cottage Artists' Garden Cottage Clean & Beautiful, vacation rental in Ashland

High Street Cottage Artists' Garden Cottage Clean & Beautiful

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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In the historic railroad district, walking distance to all the best of Ashland!, vacation rental in Ashland
In the historic railroad district, walking distance to all the best of Ashland!, vacation rental in Ashland
In the historic railroad district, walking distance to all the best of Ashland!, vacation rental in Ashland

In the historic railroad district, walking distance to all the best of Ashland!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Walk to town from this Charming Cottage., vacation rental in Ashland
Walk to town from this Charming Cottage., vacation rental in Ashland
Walk to town from this Charming Cottage., vacation rental in Ashland

Walk to town from this Charming Cottage.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Brand New Custom Ashland Home with Fantastic Mountain Views, vacation rental in Ashland
Brand New Custom Ashland Home with Fantastic Mountain Views, vacation rental in Ashland
Brand New Custom Ashland Home with Fantastic Mountain Views, vacation rental in Ashland

Brand New Custom Ashland Home with Fantastic Mountain Views

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Madrone House, Country Getaway with Panoramic Views, vacation rental in Ashland
The Madrone House, Country Getaway with Panoramic Views, vacation rental in Ashland
The Madrone House, Country Getaway with Panoramic Views, vacation rental in Ashland

The Madrone House, Country Getaway with Panoramic Views

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Stone's Throw Bungalow ~ Walk to Plays, Licensed/Legal, Private Entrance, Garden, vacation rental in Ashland
Stone's Throw Bungalow ~ Walk to Plays, Licensed/Legal, Private Entrance, Garden, vacation rental in Ashland
Stone's Throw Bungalow ~ Walk to Plays, Licensed/Legal, Private Entrance, Garden, vacation rental in Ashland

Stone's Throw Bungalow ~ Walk to Plays, Licensed/Legal, Private Entrance, Garden

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Perfect Vacation Cottage, vacation rental in Ashland
The Perfect Vacation Cottage, vacation rental in Ashland
The Perfect Vacation Cottage, vacation rental in Ashland

The Perfect Vacation Cottage

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning studio, Italian Motif, Walk to Town., vacation rental in Ashland
Stunning studio, Italian Motif, Walk to Town., vacation rental in Ashland
Stunning studio, Italian Motif, Walk to Town., vacation rental in Ashland

Stunning studio, Italian Motif, Walk to Town.

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Mt. Ashland Homestead's  Secluded Forest House, 15 minutes from Ashland, vacation rental in Ashland
Mt. Ashland Homestead's  Secluded Forest House, 15 minutes from Ashland, vacation rental in Ashland
Mt. Ashland Homestead's  Secluded Forest House, 15 minutes from Ashland, vacation rental in Ashland

Mt. Ashland Homestead's Secluded Forest House, 15 minutes from Ashland

Rental Home
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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BookStayHop - #33 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub, vacation rental in Ashland
BookStayHop - #33 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub, vacation rental in Ashland
BookStayHop - #33 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub, vacation rental in Ashland

BookStayHop - #33 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Hyatt Lake Mountain Retreat, vacation rental in Ashland
Hyatt Lake Mountain Retreat, vacation rental in Ashland
Hyatt Lake Mountain Retreat, vacation rental in Ashland

Hyatt Lake Mountain Retreat

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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BLOSSOM VIEW COTTAGES  -  Charming Home near OSF Plaza and Downtown, vacation rental in Ashland
BLOSSOM VIEW COTTAGES  -  Charming Home near OSF Plaza and Downtown, vacation rental in Ashland
BLOSSOM VIEW COTTAGES  -  Charming Home near OSF Plaza and Downtown, vacation rental in Ashland

BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Vineyard Home w/ 360 Views, private walking, pet-friendly, 2 miles from town!, vacation rental in Ashland
Vineyard Home w/ 360 Views, private walking, pet-friendly, 2 miles from town!, vacation rental in Ashland
Vineyard Home w/ 360 Views, private walking, pet-friendly, 2 miles from town!, vacation rental in Ashland

Vineyard Home w/ 360 Views, private walking, pet-friendly, 2 miles from town!

Rental Home
6 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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ArtYcottage  UNBELIEVEABLE..., vacation rental in Ashland
ArtYcottage  UNBELIEVEABLE..., vacation rental in Ashland
ArtYcottage  UNBELIEVEABLE..., vacation rental in Ashland

ArtYcottage UNBELIEVEABLE...

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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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, vacation rental in Ashland
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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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In the Heart of Town, Charming Historic Home, Quintessential Ashland!, vacation rental in Ashland
In the Heart of Town, Charming Historic Home, Quintessential Ashland!, vacation rental in Ashland
In the Heart of Town, Charming Historic Home, Quintessential Ashland!, vacation rental in Ashland

In the Heart of Town, Charming Historic Home, Quintessential Ashland!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stacy's 2nd St Cottage. Steps to downtown., vacation rental in Ashland
Stacy's 2nd St Cottage. Steps to downtown., vacation rental in Ashland
Stacy's 2nd St Cottage. Steps to downtown., vacation rental in Ashland

Stacy's 2nd St Cottage. Steps to downtown.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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BookStayHop - The Pioneer - Craftsman House - Closest to OSF!, vacation rental in Ashland
BookStayHop - The Pioneer - Craftsman House - Closest to OSF!, vacation rental in Ashland
BookStayHop - The Pioneer - Craftsman House - Closest to OSF!, vacation rental in Ashland

BookStayHop - The Pioneer - Craftsman House - Closest to OSF!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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ArtYCottage - custom furniture and art through out. Secluded and fabulous!, vacation rental in Ashland
ArtYCottage - custom furniture and art through out. Secluded and fabulous!, vacation rental in Ashland
ArtYCottage - custom furniture and art through out. Secluded and fabulous!, vacation rental in Ashland

ArtYCottage - custom furniture and art through out. Secluded and fabulous!

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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The Terra Cottage Inn a beautiful Luxury Apartment, vacation rental in Ashland
The Terra Cottage Inn a beautiful Luxury Apartment, vacation rental in Ashland
The Terra Cottage Inn a beautiful Luxury Apartment, vacation rental in Ashland

The Terra Cottage Inn a beautiful Luxury Apartment

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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The Terra Cottage Inn - Ashland, Oregon, vacation rental in Ashland
The Terra Cottage Inn - Ashland, Oregon, vacation rental in Ashland
The Terra Cottage Inn - Ashland, Oregon, vacation rental in Ashland

The Terra Cottage Inn - Ashland, Oregon

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland, vacation rental in Ashland
Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland, vacation rental in Ashland
Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland, vacation rental in Ashland

Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland, vacation rental in Ashland
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland, vacation rental in Ashland
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland, vacation rental in Ashland

Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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BookStayHop - #44 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub, vacation rental in Ashland
BookStayHop - #44 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub, vacation rental in Ashland
BookStayHop - #44 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub, vacation rental in Ashland

BookStayHop - #44 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Brand New Guesthouse - 15-Minute Easy Walk to Theaters, Plaza; Historic Ashland, vacation rental in Ashland
Brand New Guesthouse - 15-Minute Easy Walk to Theaters, Plaza; Historic Ashland, vacation rental in Ashland
Brand New Guesthouse - 15-Minute Easy Walk to Theaters, Plaza; Historic Ashland, vacation rental in Ashland

Brand New Guesthouse - 15-Minute Easy Walk to Theaters, Plaza; Historic Ashland

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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ORCHARD SUITE - Private, Safe & Comfortable Getaway! Hot tub, Pet friendly, vacation rental in Ashland
ORCHARD SUITE - Private, Safe & Comfortable Getaway! Hot tub, Pet friendly, vacation rental in Ashland
ORCHARD SUITE - Private, Safe & Comfortable Getaway! Hot tub, Pet friendly, vacation rental in Ashland

ORCHARD SUITE - Private, Safe & Comfortable Getaway! Hot tub, Pet friendly

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Hyatt Praire Mountain Cabin, vacation rental in Ashland
Hyatt Praire Mountain Cabin, vacation rental in Ashland
Hyatt Praire Mountain Cabin, vacation rental in Ashland

Hyatt Praire Mountain Cabin

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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The Maple Apartment at Tudor House Vacation Rentals, vacation rental in Ashland
The Maple Apartment at Tudor House Vacation Rentals, vacation rental in Ashland
The Maple Apartment at Tudor House Vacation Rentals, vacation rental in Ashland

The Maple Apartment at Tudor House Vacation Rentals

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Premier Downstairs Flat in Perfect Down Town Location, vacation rental in Ashland
Premier Downstairs Flat in Perfect Down Town Location, vacation rental in Ashland
Premier Downstairs Flat in Perfect Down Town Location, vacation rental in Ashland

Premier Downstairs Flat in Perfect Down Town Location

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Quiet and peaceful cottage close to downtown, vacation rental in Ashland
Quiet and peaceful cottage close to downtown, vacation rental in Ashland
Quiet and peaceful cottage close to downtown, vacation rental in Ashland

Quiet and peaceful cottage close to downtown

Rental Home
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Country Setting, five minute drive to Ashland and a short walk to Emigrant Lake, vacation rental in Ashland
Country Setting, five minute drive to Ashland and a short walk to Emigrant Lake, vacation rental in Ashland
Country Setting, five minute drive to Ashland and a short walk to Emigrant Lake, vacation rental in Ashland

Country Setting, five minute drive to Ashland and a short walk to Emigrant Lake

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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COZY cottage near Lithia Park and Town!  Ashland, OR, vacation rental in Ashland
COZY cottage near Lithia Park and Town!  Ashland, OR, vacation rental in Ashland
COZY cottage near Lithia Park and Town!  Ashland, OR, vacation rental in Ashland

COZY cottage near Lithia Park and Town! Ashland, OR

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Intimate Comfort in a vintage neighborhood 4 blocks walk to Ashland Plaza., vacation rental in Ashland
Intimate Comfort in a vintage neighborhood 4 blocks walk to Ashland Plaza., vacation rental in Ashland
Intimate Comfort in a vintage neighborhood 4 blocks walk to Ashland Plaza., vacation rental in Ashland

Intimate Comfort in a vintage neighborhood 4 blocks walk to Ashland Plaza.

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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The High Street Cottage An Artists' Garden Cottage, vacation rental in Ashland
The High Street Cottage An Artists' Garden Cottage, vacation rental in Ashland
The High Street Cottage An Artists' Garden Cottage, vacation rental in Ashland

The High Street Cottage An Artists' Garden Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charming, Comfortable Garden Studio Above The University., vacation rental in Ashland
Charming, Comfortable Garden Studio Above The University., vacation rental in Ashland
Charming, Comfortable Garden Studio Above The University., vacation rental in Ashland

Charming, Comfortable Garden Studio Above The University.

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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BookStayHop - Whispering Pines Cabin Retreat ~ Dog Friendly ~ Full Kitchen, vacation rental in Ashland
BookStayHop - Whispering Pines Cabin Retreat ~ Dog Friendly ~ Full Kitchen, vacation rental in Ashland
BookStayHop - Whispering Pines Cabin Retreat ~ Dog Friendly ~ Full Kitchen, vacation rental in Ashland

BookStayHop - Whispering Pines Cabin Retreat ~ Dog Friendly ~ Full Kitchen

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hyatt Prairie Mountain Cabin, vacation rental in Ashland
Hyatt Prairie Mountain Cabin, vacation rental in Ashland
Hyatt Prairie Mountain Cabin, vacation rental in Ashland

Hyatt Prairie Mountain Cabin

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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The Dogwood Suite at Tudor House Vacation Rentals, vacation rental in Ashland
The Dogwood Suite at Tudor House Vacation Rentals, vacation rental in Ashland
The Dogwood Suite at Tudor House Vacation Rentals, vacation rental in Ashland

The Dogwood Suite at Tudor House Vacation Rentals

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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BookStayHop - Blue Moon House ~ Just Five Blocks from OSF!~ Gourmet Kitchen, vacation rental in Ashland
BookStayHop - Blue Moon House ~ Just Five Blocks from OSF!~ Gourmet Kitchen, vacation rental in Ashland
BookStayHop - Blue Moon House ~ Just Five Blocks from OSF!~ Gourmet Kitchen, vacation rental in Ashland

BookStayHop - Blue Moon House ~ Just Five Blocks from OSF!~ Gourmet Kitchen

Rental Home
5 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
More info
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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, vacation rental in Ashland
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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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BookStayHop - #46 The Cabins on Hyatt Prairie - Sleeps 5-Dog Friendly, vacation rental in Ashland
BookStayHop - #46 The Cabins on Hyatt Prairie - Sleeps 5-Dog Friendly, vacation rental in Ashland
BookStayHop - #46 The Cabins on Hyatt Prairie - Sleeps 5-Dog Friendly, vacation rental in Ashland

BookStayHop - #46 The Cabins on Hyatt Prairie - Sleeps 5-Dog Friendly

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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BookStayHop - The Pioneer House -North Suite (Upstairs) - Closest to OSF!, vacation rental in Ashland
BookStayHop - The Pioneer House -North Suite (Upstairs) - Closest to OSF!, vacation rental in Ashland
BookStayHop - The Pioneer House -North Suite (Upstairs) - Closest to OSF!, vacation rental in Ashland

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Helman Street Penthouse with a View, vacation rental in Ashland
Helman Street Penthouse with a View, vacation rental in Ashland
Helman Street Penthouse with a View, vacation rental in Ashland

Helman Street Penthouse with a View

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Spacious B Street Beauty, Around the Corner from Festival, vacation rental in Ashland
Spacious B Street Beauty, Around the Corner from Festival, vacation rental in Ashland
Spacious B Street Beauty, Around the Corner from Festival, vacation rental in Ashland

Spacious B Street Beauty, Around the Corner from Festival

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Ashland Cabin - 170 Acres w/Mountain Views & Sauna, vacation rental in Ashland
Ashland Cabin - 170 Acres w/Mountain Views & Sauna, vacation rental in Ashland
Ashland Cabin - 170 Acres w/Mountain Views & Sauna, vacation rental in Ashland

Ashland Cabin - 170 Acres w/Mountain Views & Sauna

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Showing results 1-50 of 181

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.