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Ashland Vacation Rentals

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181 rentals in Ashland.
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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

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
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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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
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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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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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!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stacy's 2nd St Cottages .. Steps to theaters, Lithia Park and downtown Ashland, vacation rental in Ashland
Stacy's 2nd St Cottages .. Steps to theaters, Lithia Park and downtown Ashland, vacation rental in Ashland
Stacy's 2nd St Cottages .. Steps to theaters, Lithia Park and downtown Ashland, vacation rental in Ashland

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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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!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
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Charming historic cottage just 4 blocks from downtown (Licensed PA 17-248), vacation rental in Ashland
Charming historic cottage just 4 blocks from downtown (Licensed PA 17-248), vacation rental in Ashland
Charming historic cottage just 4 blocks from downtown (Licensed PA 17-248), vacation 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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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.

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
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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
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The Aloha House~ Hot Tub~ Seasonal Pool, vacation rental in Ashland
The Aloha House~ Hot Tub~ Seasonal Pool, vacation rental in Ashland
The Aloha House~ Hot Tub~ Seasonal Pool, vacation rental in Ashland

The Aloha House~ Hot Tub~ Seasonal Pool

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Hyatt Prairie Cabin #33 ~ Hot Tub, vacation rental in Ashland
Hyatt Prairie Cabin #33 ~ Hot Tub, vacation rental in Ashland
Hyatt Prairie Cabin #33 ~ Hot Tub, vacation rental in Ashland

Hyatt Prairie Cabin #33 ~ Hot Tub

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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...

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stone's Throw Bungalow ~ Walk to Plays, Licensed/Legal, Private Entrance, Garden

Holiday Rental House
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

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

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
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Hyatt Prairie Cabin #46~ Hot Tub~ Dog Friendly, vacation rental in Ashland
Hyatt Prairie Cabin #46~ Hot Tub~ Dog Friendly, vacation rental in Ashland
Hyatt Prairie Cabin #46~ Hot Tub~ Dog Friendly, vacation rental in Ashland

Hyatt Prairie Cabin #46~ Hot Tub~ Dog Friendly

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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!

Holiday Rental House
1 bedroom
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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Hyatt Prairie Cabin #44 ~ Hot Tub, vacation rental in Ashland
Hyatt Prairie Cabin #44 ~ Hot Tub, vacation rental in Ashland
Hyatt Prairie Cabin #44 ~ Hot Tub, vacation rental in Ashland

Hyatt Prairie Cabin #44 ~ Hot Tub

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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
2 bedrooms
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
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Stunning studio, Italian Motif, Walk to Town.

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Come relax, work & enjoy country air.  Winter is beautiful.  WiFi., vacation rental in Ashland
Come relax, work & enjoy country air.  Winter is beautiful.  WiFi., vacation rental in Ashland
Come relax, work & enjoy country air.  Winter is beautiful.  WiFi., vacation rental in Ashland

Come relax, work & enjoy country air. Winter is beautiful. WiFi.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Space Next to Everything, Walk Anywhere!, vacation rental in Ashland
Charming Space Next to Everything, Walk Anywhere!, vacation rental in Ashland
Charming Space Next to Everything, Walk Anywhere!, vacation rental in Ashland

Charming Space Next to Everything, Walk Anywhere!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den  Near Theaters, Downtown, vacation rental in Ashland
BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den  Near Theaters, Downtown, vacation rental in Ashland
BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den  Near Theaters, Downtown, vacation rental in Ashland

BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
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

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 10
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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private Suite Near Shakespeare, vacation rental in Ashland
Private Suite Near Shakespeare, vacation rental in Ashland
Private Suite Near Shakespeare, vacation rental in Ashland

Private Suite Near Shakespeare

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Pioneer North Suite (Upstairs)~ Close to OSF, vacation rental in Ashland
Pioneer North Suite (Upstairs)~ Close to OSF, vacation rental in Ashland
Pioneer North Suite (Upstairs)~ Close to OSF, vacation rental in Ashland

Pioneer North Suite (Upstairs)~ Close to OSF

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Pioneer Craftsman- Closest to OSF!, vacation rental in Ashland
Pioneer Craftsman- Closest to OSF!, vacation rental in Ashland
Pioneer Craftsman- Closest to OSF!, vacation rental in Ashland

Pioneer Craftsman- Closest to OSF!

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

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

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
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!

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Hyatt Prairie Cabin #45 ~ Hot Tub, vacation rental in Ashland
Hyatt Prairie Cabin #45 ~ Hot Tub, vacation rental in Ashland
Hyatt Prairie Cabin #45 ~ Hot Tub, vacation rental in Ashland

Hyatt Prairie Cabin #45 ~ Hot Tub

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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.

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

Helman House-Three Blocks from the Oregon Shakespeare Festival

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Whispering Pines~ Dog Friendly ~Kitchen, vacation rental in Ashland
Whispering Pines~ Dog Friendly ~Kitchen, vacation rental in Ashland
Whispering Pines~ Dog Friendly ~Kitchen, vacation rental in Ashland

Whispering Pines~ Dog Friendly ~Kitchen

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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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
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