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Ashland Vacation Rentals

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5 mi
168 rentals in Ashland.
Hargadine House: The Carriage House, vacation rental in Ashland
Hargadine House: The Carriage House, vacation rental in Ashland
Hargadine House: The Carriage House, vacation rental in Ashland

Hargadine House: The Carriage House

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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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
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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
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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 4
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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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
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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
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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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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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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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
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Walk to Downtown/Theaters from this Charming Home , vacation rental in Ashland
Walk to Downtown/Theaters from this Charming Home , vacation rental in Ashland
Walk to Downtown/Theaters from this Charming Home , vacation rental in Ashland

Walk to Downtown/Theaters from this Charming Home

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stone's Throw Bungalow - Licensed, Private Garden, vacation rental in Ashland
Stone's Throw Bungalow - Licensed, Private Garden, vacation rental in Ashland
Stone's Throw Bungalow - Licensed, Private Garden, vacation rental in Ashland

Stone's Throw Bungalow - Licensed, Private Garden

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Newly Remodeled Guest Suite with Private Deck Overlooking Forest and Waterfall, vacation rental in Ashland
Newly Remodeled Guest Suite with Private Deck Overlooking Forest and Waterfall, vacation rental in Ashland
Newly Remodeled Guest Suite with Private Deck Overlooking Forest and Waterfall, vacation rental in Ashland

Newly Remodeled Guest Suite with Private Deck Overlooking Forest and Waterfall

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 6
Match: Sleeps
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Helman House, vacation rental in Ashland
Helman House, vacation rental in Ashland
Helman House, vacation rental in Ashland

Helman House

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
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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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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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
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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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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
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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
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Downtown Ashland private cottage with garden patio, vacation rental in Ashland
Downtown Ashland private cottage with garden patio, vacation rental in Ashland
Downtown Ashland private cottage with garden patio, vacation rental in Ashland

Downtown Ashland private cottage with garden patio

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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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 10
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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230-Downstairs-Duplex-Private Bathroom-Mountain View, vacation rental in Ashland
230-Downstairs-Duplex-Private Bathroom-Mountain View, vacation rental in Ashland
230-Downstairs-Duplex-Private Bathroom-Mountain View, vacation rental in Ashland

230-Downstairs-Duplex-Private Bathroom-Mountain View

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Custom Ashland Home with Fantastic Mountain Views, vacation rental in Ashland
Custom Ashland Home with Fantastic Mountain Views, vacation rental in Ashland
Custom Ashland Home with Fantastic Mountain Views, vacation rental in Ashland

Custom Ashland Home with Fantastic Mountain Views

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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East Main Downtown Bungalow, vacation rental in Ashland
East Main Downtown Bungalow, vacation rental in Ashland
East Main Downtown Bungalow, vacation rental in Ashland

East Main Downtown Bungalow

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Sunset Chalet - 2600 sq.ft. Multi-Seasonal retreat only15 minutes from Ashland !, vacation rental in Ashland
Sunset Chalet - 2600 sq.ft. Multi-Seasonal retreat only15 minutes from Ashland !, vacation rental in Ashland
Sunset Chalet - 2600 sq.ft. Multi-Seasonal retreat only15 minutes from Ashland !, vacation rental in Ashland

Sunset Chalet - 2600 sq.ft. Multi-Seasonal retreat only15 minutes from Ashland !

Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
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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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
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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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

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Country experience close to downtown Ashland, vacation rental in Ashland
Country experience close to downtown Ashland, vacation rental in Ashland
Country experience close to downtown Ashland, vacation rental in Ashland

Country experience close to downtown Ashland

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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
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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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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, vacation rental in Ashland
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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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2nd Street Cottages, GARDEN SUITE, vacation rental in Ashland
2nd Street Cottages, GARDEN SUITE, vacation rental in Ashland
2nd Street Cottages, GARDEN SUITE, vacation rental in Ashland

2nd Street Cottages, GARDEN SUITE

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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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
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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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Country Setting, five minute drive to Ashland close to Emigrant Lake, vacation rental in Ashland
Country Setting, five minute drive to Ashland close to Emigrant Lake, vacation rental in Ashland
Country Setting, five minute drive to Ashland close to Emigrant Lake, vacation rental in Ashland

Country Setting, five minute drive to Ashland close to Emigrant Lake

Condo/Apartment
0 bedrooms
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
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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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
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Country's Edge Rooms in just outside of Ashland, convenient for travel, vacation rental in Ashland
Country's Edge Rooms in just outside of Ashland, convenient for travel, vacation rental in Ashland
Country's Edge Rooms in just outside of Ashland, convenient for travel, vacation rental in Ashland

Country's Edge Rooms in just outside of Ashland, convenient for travel

Rental Home
1 bedroom
0 bathrooms
Sleeps 2
Match: Sleeps
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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
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Lodge Room 7 * GSI&C, vacation rental in Ashland
Lodge Room 7 * GSI&C, vacation rental in Ashland
Lodge Room 7 * GSI&C, vacation rental in Ashland

Lodge Room 7 * GSI&C

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lodge Room 6 * GSI&C, vacation rental in Ashland
Lodge Room 6 * GSI&C, vacation rental in Ashland
Lodge Room 6 * GSI&C, vacation rental in Ashland

Lodge Room 6 * GSI&C

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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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
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Lodge Room 4 * GSI&C, vacation rental in Ashland
Lodge Room 4 * GSI&C, vacation rental in Ashland
Lodge Room 4 * GSI&C, vacation rental in Ashland

Lodge Room 4 * GSI&C

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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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
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Lodge Room 3 * GSI&C, vacation rental in Ashland
Lodge Room 3 * GSI&C, vacation rental in Ashland
Lodge Room 3 * GSI&C, vacation rental in Ashland

Lodge Room 3 * GSI&C

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Showing results 1-50 of 168
Frequently Asked Questions about Ashland






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.