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Holiday Rentals in Ashland

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180 rentals in Ashland.
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The Ashland Cottage, walk to town, holiday rental in Ashland
The Ashland Cottage, walk to town, holiday rental in Ashland
The Ashland Cottage, walk to town, holiday rental in Ashland

The Ashland Cottage, walk to town

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Hanna's House- Your Home Away from Home, holiday rental in Ashland
Hanna's House- Your Home Away from Home, holiday rental in Ashland
Hanna's House- Your Home Away from Home, holiday rental in Ashland

Hanna's House- Your Home Away from Home

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Stacy's 2nd St Cottage. Steps to downtown., holiday rental in Ashland
Stacy's 2nd St Cottage. Steps to downtown., holiday rental in Ashland
Stacy's 2nd St Cottage. Steps to downtown., holiday rental in Ashland

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Craftsman Style Home In Country Setting, holiday rental in Ashland
Craftsman Style Home In Country Setting, holiday rental in Ashland
Craftsman Style Home In Country Setting, holiday rental in Ashland

Craftsman Style Home In Country Setting

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Brand New Custom Ashland Home with Fantastic Mountain Views, holiday rental in Ashland
Brand New Custom Ashland Home with Fantastic Mountain Views, holiday rental in Ashland
Brand New Custom Ashland Home with Fantastic Mountain Views, holiday rental in Ashland

Brand New Custom Ashland Home with Fantastic Mountain Views

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Railroad District, steps to downtown, everything you need to enjoy Ashland!, holiday rental in Ashland
Railroad District, steps to downtown, everything you need to enjoy Ashland!, holiday rental in Ashland
Railroad District, steps to downtown, everything you need to enjoy Ashland!, holiday rental in Ashland

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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High Street Cottage Artists' Garden Cottage Clean & Beautiful, holiday rental in Ashland
High Street Cottage Artists' Garden Cottage Clean & Beautiful, holiday rental in Ashland
High Street Cottage Artists' Garden Cottage Clean & Beautiful, holiday rental in Ashland

High Street Cottage Artists' Garden Cottage Clean & Beautiful

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Walk to town from this Charming Cottage., holiday rental in Ashland
Walk to town from this Charming Cottage., holiday rental in Ashland
Walk to town from this Charming Cottage., holiday rental in Ashland

Walk to town from this Charming Cottage.

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Perfect Vacation Cottage, holiday rental in Ashland
The Perfect Vacation Cottage, holiday rental in Ashland
The Perfect Vacation Cottage, holiday rental in Ashland

The Perfect Vacation Cottage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Charming historic cottage just 4 blocks from downtown (Licensed PA 17-248), holiday rental in Ashland
Charming historic cottage just 4 blocks from downtown (Licensed PA 17-248), holiday rental in Ashland
Charming historic cottage just 4 blocks from downtown (Licensed PA 17-248), holiday rental in Ashland

Charming historic cottage just 4 blocks from downtown (Licensed PA 17-248)

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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The Madrone House, Country Getaway with Panoramic Views, holiday rental in Ashland
The Madrone House, Country Getaway with Panoramic Views, holiday rental in Ashland
The Madrone House, Country Getaway with Panoramic Views, holiday rental in Ashland

The Madrone House, Country Getaway with Panoramic Views

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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The Maple Apartment at Tudor House Vacation Rentals, holiday rental in Ashland
The Maple Apartment at Tudor House Vacation Rentals, holiday rental in Ashland
The Maple Apartment at Tudor House Vacation Rentals, holiday 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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Brand New Guesthouse - 15-Minute Easy Walk to Theaters, Plaza; Historic Ashland, holiday rental in Ashland
Brand New Guesthouse - 15-Minute Easy Walk to Theaters, Plaza; Historic Ashland, holiday rental in Ashland
Brand New Guesthouse - 15-Minute Easy Walk to Theaters, Plaza; Historic Ashland, holiday rental in Ashland

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Hyatt Lake Mountain Retreat, holiday rental in Ashland
Hyatt Lake Mountain Retreat, holiday rental in Ashland
Hyatt Lake Mountain Retreat, holiday rental in Ashland

Hyatt Lake Mountain Retreat

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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ArtYcottage  UNBELIEVEABLE..., holiday rental in Ashland
ArtYcottage  UNBELIEVEABLE..., holiday rental in Ashland
ArtYcottage  UNBELIEVEABLE..., holiday rental in Ashland

ArtYcottage UNBELIEVEABLE...

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland, holiday rental in Ashland
Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland, holiday rental in Ashland
Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland, holiday 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
More info
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In the historic railroad district, walking distance to all the best of Ashland!, holiday rental in Ashland
In the historic railroad district, walking distance to all the best of Ashland!, holiday rental in Ashland
In the historic railroad district, walking distance to all the best of Ashland!, holiday rental in Ashland

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Mt. Ashland Homestead's  Secluded Forest House, 15 minutes from Ashland, holiday rental in Ashland
Mt. Ashland Homestead's  Secluded Forest House, 15 minutes from Ashland, holiday rental in Ashland
Mt. Ashland Homestead's  Secluded Forest House, 15 minutes from Ashland, holiday rental in Ashland

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
More info
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Stone's Throw Bungalow ~ Walk to Plays, Licensed/Legal, Private Entrance, Garden, holiday rental in Ashland
Stone's Throw Bungalow ~ Walk to Plays, Licensed/Legal, Private Entrance, Garden, holiday rental in Ashland
Stone's Throw Bungalow ~ Walk to Plays, Licensed/Legal, Private Entrance, Garden, holiday rental in Ashland

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Asian Inspired Escape with View - Just 3 Miles from Downtown, holiday rental in Ashland
Asian Inspired Escape with View - Just 3 Miles from Downtown, holiday rental in Ashland
Asian Inspired Escape with View - Just 3 Miles from Downtown, holiday rental in Ashland

Asian Inspired Escape with View - Just 3 Miles from Downtown

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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ORCHARD SUITE - Private, Safe & Comfortable Getaway! Hot tub, Pet friendly, holiday rental in Ashland
ORCHARD SUITE - Private, Safe & Comfortable Getaway! Hot tub, Pet friendly, holiday rental in Ashland
ORCHARD SUITE - Private, Safe & Comfortable Getaway! Hot tub, Pet friendly, holiday rental in Ashland

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Vineyard Home w/ 360 Views, private walking, pet-friendly, 2 miles from town!, holiday rental in Ashland
Vineyard Home w/ 360 Views, private walking, pet-friendly, 2 miles from town!, holiday rental in Ashland
Vineyard Home w/ 360 Views, private walking, pet-friendly, 2 miles from town!, holiday rental in Ashland

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

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
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Hyatt Praire Mountain Cabin, holiday rental in Ashland
Hyatt Praire Mountain Cabin, holiday rental in Ashland
Hyatt Praire Mountain Cabin, holiday rental in Ashland

Hyatt Praire Mountain Cabin

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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BLOSSOM VIEW COTTAGES  -  Charming Home near OSF Plaza and Downtown, holiday rental in Ashland
BLOSSOM VIEW COTTAGES  -  Charming Home near OSF Plaza and Downtown, holiday rental in Ashland
BLOSSOM VIEW COTTAGES  -  Charming Home near OSF Plaza and Downtown, holiday rental in Ashland

BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Terra Cottage Inn a beautiful Luxury Apartment, holiday rental in Ashland
The Terra Cottage Inn a beautiful Luxury Apartment, holiday rental in Ashland
The Terra Cottage Inn a beautiful Luxury Apartment, holiday rental in Ashland

The Terra Cottage Inn a beautiful Luxury Apartment

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Payment Protection

The Terra Cottage Inn - Ashland, Oregon, holiday rental in Ashland
The Terra Cottage Inn - Ashland, Oregon, holiday rental in Ashland
The Terra Cottage Inn - Ashland, Oregon, holiday rental in Ashland

The Terra Cottage Inn - Ashland, Oregon

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland, holiday rental in Ashland
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland, holiday rental in Ashland
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland, holiday 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 - #46 The Cabins on Hyatt Prairie -Hot Tub- Sleeps 5-Dog Friendly, holiday rental in Ashland
BookStayHop - #46 The Cabins on Hyatt Prairie -Hot Tub- Sleeps 5-Dog Friendly, holiday rental in Ashland
BookStayHop - #46 The Cabins on Hyatt Prairie -Hot Tub- Sleeps 5-Dog Friendly, holiday rental in Ashland

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Stunning studio, Italian Motif, Walk to Town., holiday rental in Ashland
Stunning studio, Italian Motif, Walk to Town., holiday rental in Ashland
Stunning studio, Italian Motif, Walk to Town., holiday rental in Ashland

Stunning studio, Italian Motif, Walk to Town.

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Quiet and peaceful cottage close to downtown, holiday rental in Ashland
Quiet and peaceful cottage close to downtown, holiday rental in Ashland
Quiet and peaceful cottage close to downtown, holiday rental in Ashland

Quiet and peaceful cottage close to downtown

Holiday Rental House
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, holiday rental in Ashland
Country Setting, five minute drive to Ashland and a short walk to Emigrant Lake, holiday rental in Ashland
Country Setting, five minute drive to Ashland and a short walk to Emigrant Lake, holiday 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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ArtYCottage - custom furniture and art through out. Secluded and fabulous!, holiday rental in Ashland
ArtYCottage - custom furniture and art through out. Secluded and fabulous!, holiday rental in Ashland
ArtYCottage - custom furniture and art through out. Secluded and fabulous!, holiday rental in Ashland

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

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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BookStayHop - #33 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub, holiday rental in Ashland
BookStayHop - #33 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub, holiday rental in Ashland
BookStayHop - #33 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub, holiday rental in Ashland

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Hyatt Prairie Mountain Cabin, holiday rental in Ashland
Hyatt Prairie Mountain Cabin, holiday rental in Ashland
Hyatt Prairie Mountain Cabin, holiday rental in Ashland

Hyatt Prairie Mountain Cabin

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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The Dogwood Suite at Tudor House Vacation Rentals, holiday rental in Ashland
The Dogwood Suite at Tudor House Vacation Rentals, holiday rental in Ashland
The Dogwood Suite at Tudor House Vacation Rentals, holiday 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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The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean, holiday rental in Ashland
The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean, holiday rental in Ashland
The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean, holiday rental in Ashland

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

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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The Red Dragon House, holiday rental in Ashland
The Red Dragon House, holiday rental in Ashland
The Red Dragon House, holiday rental in Ashland

The Red Dragon House

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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BookStayHop - The Pioneer - Craftsman House - Closest to OSF!, holiday rental in Ashland
BookStayHop - The Pioneer - Craftsman House - Closest to OSF!, holiday rental in Ashland
BookStayHop - The Pioneer - Craftsman House - Closest to OSF!, holiday rental in Ashland

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Premier Downstairs Flat in Perfect Down Town Location, holiday rental in Ashland
Premier Downstairs Flat in Perfect Down Town Location, holiday rental in Ashland
Premier Downstairs Flat in Perfect Down Town Location, holiday rental in Ashland

Premier Downstairs Flat in Perfect Down Town Location

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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OCTOBER  in COZY cottage near Lithia Park and Town!  Ashland, OR, holiday rental in Ashland
OCTOBER  in COZY cottage near Lithia Park and Town!  Ashland, OR, holiday rental in Ashland
OCTOBER  in COZY cottage near Lithia Park and Town!  Ashland, OR, holiday rental in Ashland

OCTOBER in COZY cottage near Lithia Park and Town! Ashland, OR

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Ashland Cabin - 170 Acres w/Mountain Views & Sauna, holiday rental in Ashland
Ashland Cabin - 170 Acres w/Mountain Views & Sauna, holiday rental in Ashland
Ashland Cabin - 170 Acres w/Mountain Views & Sauna, holiday rental in Ashland

Ashland Cabin - 170 Acres w/Mountain Views & Sauna

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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In the Heart of Town, Charming Historic Home, Quintessential Ashland!, holiday rental in Ashland
In the Heart of Town, Charming Historic Home, Quintessential Ashland!, holiday rental in Ashland
In the Heart of Town, Charming Historic Home, Quintessential Ashland!, holiday rental in Ashland

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Intimate Comfort in a vintage neighborhood 4 blocks walk to Ashland Plaza., holiday rental in Ashland
Intimate Comfort in a vintage neighborhood 4 blocks walk to Ashland Plaza., holiday rental in Ashland
Intimate Comfort in a vintage neighborhood 4 blocks walk to Ashland Plaza., holiday rental in Ashland

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Abigail's Two Bedroom Vacation Cottage, easy 10-min. walk to plaza/theaters/shop, holiday rental in Ashland
Abigail's Two Bedroom Vacation Cottage, easy 10-min. walk to plaza/theaters/shop, holiday rental in Ashland
Abigail's Two Bedroom Vacation Cottage, easy 10-min. walk to plaza/theaters/shop, holiday rental in Ashland

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Payment Protection

Charming, Comfortable Garden Studio Above The University., holiday rental in Ashland
Charming, Comfortable Garden Studio Above The University., holiday rental in Ashland
Charming, Comfortable Garden Studio Above The University., holiday rental in Ashland

Charming, Comfortable Garden Studio Above The University.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Helman House-Three Blocks from the Oregon Shakespeare Festival, holiday rental in Ashland
Helman House-Three Blocks from the Oregon Shakespeare Festival, holiday rental in Ashland
Helman House-Three Blocks from the Oregon Shakespeare Festival, holiday rental in Ashland

Helman House-Three Blocks from the Oregon Shakespeare Festival

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The High Street Cottage An Artists' Garden Cottage, holiday rental in Ashland
The High Street Cottage An Artists' Garden Cottage, holiday rental in Ashland
The High Street Cottage An Artists' Garden Cottage, holiday rental in Ashland

The High Street Cottage An Artists' Garden Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Payment Protection

BookStayHop - Whispering Pines Cabin Retreat ~ Dog Friendly ~ Full Kitchen, holiday rental in Ashland
BookStayHop - Whispering Pines Cabin Retreat ~ Dog Friendly ~ Full Kitchen, holiday rental in Ashland
BookStayHop - Whispering Pines Cabin Retreat ~ Dog Friendly ~ Full Kitchen, holiday rental in Ashland

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Secluded Forest Log House 15 minutes to Ashland, holiday rental in Ashland
Secluded Forest Log House 15 minutes to Ashland, holiday rental in Ashland
Secluded Forest Log House 15 minutes to Ashland, holiday rental in Ashland

Secluded Forest Log House 15 minutes to Ashland

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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BookStayHop - #44 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub, holiday rental in Ashland
BookStayHop - #44 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub, holiday rental in Ashland
BookStayHop - #44 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub, holiday rental in Ashland

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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