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Ashland Pet Friendly Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
79 rentals 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, vacation rental in Ashland

Premier Downstairs Flat in Perfect Down Town Location

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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The Red Dragon House, vacation rental in Ashland
The Red Dragon House, vacation rental in Ashland
The Red Dragon House, vacation rental in Ashland

The Red Dragon House

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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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, Pet friendly
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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, Pet friendly
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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, Pet friendly
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232-Duplex-Private Bathroom-Mountain View, vacation rental in Ashland
232-Duplex-Private Bathroom-Mountain View, vacation rental in Ashland
232-Duplex-Private Bathroom-Mountain View, vacation rental in Ashland

232-Duplex-Private Bathroom-Mountain View

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
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Courtside Cottage - WalkScore 93 - Dog Friendly, vacation rental in Ashland
Courtside Cottage - WalkScore 93 - Dog Friendly, vacation rental in Ashland
Courtside Cottage - WalkScore 93 - Dog Friendly, vacation rental in Ashland

Courtside Cottage - WalkScore 93 - Dog Friendly

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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Charming home, w/hot tub, close to downtown (pet-friendly!), vacation rental in Ashland
Charming home, w/hot tub, close to downtown (pet-friendly!), vacation rental in Ashland
Charming home, w/hot tub, close to downtown (pet-friendly!), vacation rental in Ashland

Charming home, w/hot tub, close to downtown (pet-friendly!)

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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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, Pet friendly
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New Downtown 3 Bedroom Upstairs Flat with views, vacation rental in Ashland
New Downtown 3 Bedroom Upstairs Flat with views, vacation rental in Ashland
New Downtown 3 Bedroom Upstairs Flat with views, vacation rental in Ashland

New Downtown 3 Bedroom Upstairs Flat with views

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Pet friendly
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Secluded Forest Log House 15 minutes to Ashland, vacation rental in Ashland
Secluded Forest Log House 15 minutes to Ashland, vacation rental in Ashland
Secluded Forest Log House 15 minutes to Ashland, vacation rental in Ashland

Secluded Forest Log House 15 minutes to Ashland

Rental Home
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps, Pet friendly
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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, Pet friendly
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GS Lodge Room 5~ Jacuzzi Bathtub, vacation rental in Ashland
GS Lodge Room 5~ Jacuzzi Bathtub, vacation rental in Ashland
GS Lodge Room 5~ Jacuzzi Bathtub, vacation rental in Ashland

GS Lodge Room 5~ Jacuzzi Bathtub

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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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
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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The Indigo Cottage 5 Min walk to Downtown Ashland, vacation rental in Ashland
The Indigo Cottage 5 Min walk to Downtown Ashland, vacation rental in Ashland
The Indigo Cottage 5 Min walk to Downtown Ashland, vacation rental in Ashland

The Indigo Cottage 5 Min walk to Downtown Ashland

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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QuaintStudio Retreat near OSF and DowntownAshland, vacation rental in Ashland
QuaintStudio Retreat near OSF and DowntownAshland, vacation rental in Ashland
QuaintStudio Retreat near OSF and DowntownAshland, vacation rental in Ashland

QuaintStudio Retreat near OSF and DowntownAshland

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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Downtown Ashland Earth spa unit with private patio, vacation rental in Ashland
Downtown Ashland Earth spa unit with private patio, vacation rental in Ashland
Downtown Ashland Earth spa unit with private patio, vacation rental in Ashland

Downtown Ashland Earth spa unit with private patio

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps, Pet friendly
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The Loft Nancy's Cottage Edit, vacation rental in Ashland
The Loft Nancy's Cottage Edit, vacation rental in Ashland
The Loft Nancy's Cottage Edit, vacation rental in Ashland

The Loft Nancy's Cottage Edit

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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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, Pet friendly
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Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 1, vacation rental in Ashland
Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 1, vacation rental in Ashland
Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 1, vacation rental in Ashland

Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 1

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 2, vacation rental in Ashland
Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 2, vacation rental in Ashland
Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 2, vacation rental in Ashland

Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 2

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Pet friendly
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Warm & Inviting Ashland Cottage < Half-Mile to SOU, vacation rental in Ashland
Warm & Inviting Ashland Cottage < Half-Mile to SOU, vacation rental in Ashland
Warm & Inviting Ashland Cottage < Half-Mile to SOU, vacation rental in Ashland

Warm & Inviting Ashland Cottage < Half-Mile to SOU

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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BookStayHop -#41 Cabin on Hyatt Prairie Rd- Dog Friendly, With Mountain Views., vacation rental in Ashland
BookStayHop -#41 Cabin on Hyatt Prairie Rd- Dog Friendly, With Mountain Views., vacation rental in Ashland
BookStayHop -#41 Cabin on Hyatt Prairie Rd- Dog Friendly, With Mountain Views., vacation rental in Ashland

BookStayHop -#41 Cabin on Hyatt Prairie Rd- Dog Friendly, With Mountain Views.

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, Pet friendly
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Adjacent to downtown Ashland and Lithia Park. Lithia Park Cabin, vacation rental in Ashland
Adjacent to downtown Ashland and Lithia Park. Lithia Park Cabin, vacation rental in Ashland
Adjacent to downtown Ashland and Lithia Park. Lithia Park Cabin, vacation rental in Ashland

Adjacent to downtown Ashland and Lithia Park. Lithia Park Cabin

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 3, vacation rental in Ashland
Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 3, vacation rental in Ashland
Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 3, vacation rental in Ashland

Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 3

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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, Pet friendly
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Ashland Boho-Chic with a Yard, vacation rental in Ashland
Ashland Boho-Chic with a Yard, vacation rental in Ashland
Ashland Boho-Chic with a Yard, vacation rental in Ashland

Ashland Boho-Chic with a Yard

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, Pet friendly
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Beautiful Land with creek and woods, sweet home gardens, 1 M to Ashland hospital, vacation rental in Ashland
Beautiful Land with creek and woods, sweet home gardens, 1 M to Ashland hospital, vacation rental in Ashland
Beautiful Land with creek and woods, sweet home gardens, 1 M to Ashland hospital, vacation rental in Ashland

Beautiful Land with creek and woods, sweet home gardens, 1 M to Ashland hospital

Rental Home
3 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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Expansive views at The Crest House, vacation rental in Ashland
Expansive views at The Crest House, vacation rental in Ashland
Expansive views at The Crest House, vacation rental in Ashland

Expansive views at The Crest House

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, Pet friendly
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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, Pet friendly
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Serene Secluded Home ~ Huge Balcony, Firepit & BBQ, vacation rental in Ashland
Serene Secluded Home ~ Huge Balcony, Firepit & BBQ, vacation rental in Ashland
Serene Secluded Home ~ Huge Balcony, Firepit & BBQ, vacation rental in Ashland

Serene Secluded Home ~ Huge Balcony, Firepit & BBQ

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Pet friendly
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Home Sweet Home - Relax w/  Beautiful Big Yard and Steam Shower, vacation rental in Ashland
Home Sweet Home - Relax w/  Beautiful Big Yard and Steam Shower, vacation rental in Ashland
Home Sweet Home - Relax w/  Beautiful Big Yard and Steam Shower, vacation rental in Ashland

Home Sweet Home - Relax w/ Beautiful Big Yard and Steam Shower

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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Callahan's House, vacation rental in Ashland
Callahan's House, vacation rental in Ashland
Callahan's House, vacation rental in Ashland

Callahan's House

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps, Pet friendly
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3 Bedroom Home - Walking distance to everything - Quiet on dead end street, vacation rental in Ashland
3 Bedroom Home - Walking distance to everything - Quiet on dead end street, vacation rental in Ashland
3 Bedroom Home - Walking distance to everything - Quiet on dead end street, vacation rental in Ashland

3 Bedroom Home - Walking distance to everything - Quiet on dead end street

Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps, Pet friendly
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Mountain Retreat, vacation rental in Ashland
Mountain Retreat, vacation rental in Ashland
Mountain Retreat, vacation rental in Ashland

Mountain Retreat

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
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Cattle View Ranch House, vacation rental in Ashland
Cattle View Ranch House, vacation rental in Ashland
Cattle View Ranch House, vacation rental in Ashland

Cattle View Ranch House

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps, Pet friendly
More info
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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 8
Match: Sleeps, Pet friendly
More info
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Come relax, work & enjoy country air.  Spring is here!..  WiFi., vacation rental in Ashland
Come relax, work & enjoy country air.  Spring is here!..  WiFi., vacation rental in Ashland
Come relax, work & enjoy country air.  Spring is here!..  WiFi., vacation rental in Ashland

Come relax, work & enjoy country air. Spring is here!.. WiFi.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps, Pet friendly
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Ashland lavender estate. Come stay at our farmhouse!, vacation rental in Ashland
Ashland lavender estate. Come stay at our farmhouse!, vacation rental in Ashland
Ashland lavender estate. Come stay at our farmhouse!, vacation rental in Ashland

Ashland lavender estate. Come stay at our farmhouse!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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3 Suites | Hot Tub | Downtown Ashland | Tesla Station, vacation rental in Ashland
3 Suites | Hot Tub | Downtown Ashland | Tesla Station, vacation rental in Ashland
3 Suites | Hot Tub | Downtown Ashland | Tesla Station, vacation rental in Ashland

3 Suites | Hot Tub | Downtown Ashland | Tesla Station

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, Pet friendly
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Comfortable Garden Studio 3 blocks from downtown, vacation rental in Ashland
Comfortable Garden Studio 3 blocks from downtown, vacation rental in Ashland
Comfortable Garden Studio 3 blocks from downtown, vacation rental in Ashland

Comfortable Garden Studio 3 blocks from downtown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Pet friendly
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Lodge Room 1 * GSI&C, vacation rental in Ashland
Lodge Room 1 * GSI&C, vacation rental in Ashland
Lodge Room 1 * GSI&C, vacation rental in Ashland

Lodge Room 1 * GSI&C

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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Hobart Peak Cabin w/ Jacuzzi * Green Springs Inn, vacation rental in Ashland
Hobart Peak Cabin w/ Jacuzzi * Green Springs Inn, vacation rental in Ashland
Hobart Peak Cabin w/ Jacuzzi * Green Springs Inn, vacation rental in Ashland

Hobart Peak Cabin w/ Jacuzzi * Green Springs Inn

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Pet friendly
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Quiet Garden Courtyard Studio only 3 blocks from downtown, vacation rental in Ashland
Quiet Garden Courtyard Studio only 3 blocks from downtown, vacation rental in Ashland
Quiet Garden Courtyard Studio only 3 blocks from downtown, vacation rental in Ashland

Quiet Garden Courtyard Studio only 3 blocks from downtown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Pet friendly
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1 Bedroom Suite | Hot Tub | Downtown Ashland | Tesla Station, vacation rental in Ashland
1 Bedroom Suite | Hot Tub | Downtown Ashland | Tesla Station, vacation rental in Ashland
1 Bedroom Suite | Hot Tub | Downtown Ashland | Tesla Station, vacation rental in Ashland

1 Bedroom Suite | Hot Tub | Downtown Ashland | Tesla Station

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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Soda Mountain * GSI&C, vacation rental in Ashland
Soda Mountain * GSI&C, vacation rental in Ashland
Soda Mountain * GSI&C, vacation rental in Ashland

Soda Mountain * GSI&C

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Pet friendly
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Helman House- Mega, vacation rental in Ashland
Helman House- Mega, vacation rental in Ashland
Helman House- Mega, vacation rental in Ashland

Helman House- Mega

Rental Home
4 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps, Pet friendly
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Historic Main House great for gatherings, vacation rental in Ashland
Historic Main House great for gatherings, vacation rental in Ashland
Historic Main House great for gatherings, vacation rental in Ashland

Historic Main House great for gatherings

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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Parsnip Lakes * GSI&C, vacation rental in Ashland
Parsnip Lakes * GSI&C, vacation rental in Ashland
Parsnip Lakes * GSI&C, vacation rental in Ashland

Parsnip Lakes * GSI&C

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Pet friendly
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Lodge Room 2 * GSI&C, vacation rental in Ashland
Lodge Room 2 * GSI&C, vacation rental in Ashland
Lodge Room 2 * GSI&C, vacation rental in Ashland

Lodge Room 2 * GSI&C

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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Showing results 1-50 of 179

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.