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Holiday Rentals in Ashland

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Bedrooms

Bathrooms

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5 km
168 rentals in Ashland.
Hargadine House: The Carriage House, holiday rental in Ashland
Hargadine House: The Carriage House, holiday rental in Ashland
Hargadine House: The Carriage House, holiday 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!), holiday rental in Ashland
Charming home, w/hot tub, close to downtown (pet-friendly!), holiday rental in Ashland
Charming home, w/hot tub, close to downtown (pet-friendly!), holiday rental in Ashland

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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
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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 4
Match: Sleeps
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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
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232-Duplex-Private Bathroom-Mountain View, holiday rental in Ashland
232-Duplex-Private Bathroom-Mountain View, holiday rental in Ashland
232-Duplex-Private Bathroom-Mountain View, holiday rental in Ashland

232-Duplex-Private Bathroom-Mountain View

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
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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
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BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den  Near Theaters, Downtown, holiday rental in Ashland
BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den  Near Theaters, Downtown, holiday rental in Ashland
BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den  Near Theaters, Downtown, holiday 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 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
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Walk to Downtown/Theaters from this Charming Home , holiday rental in Ashland
Walk to Downtown/Theaters from this Charming Home , holiday rental in Ashland
Walk to Downtown/Theaters from this Charming Home , holiday rental in Ashland

Walk to Downtown/Theaters from this Charming Home

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Stone's Throw Bungalow - Licensed, Private Garden, holiday rental in Ashland
Stone's Throw Bungalow - Licensed, Private Garden, holiday rental in Ashland
Stone's Throw Bungalow - Licensed, Private Garden, holiday rental in Ashland

Stone's Throw Bungalow - Licensed, Private Garden

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

Newly Remodeled Guest Suite with Private Deck Overlooking Forest and Waterfall

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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 6
Match: Sleeps
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Helman House, holiday rental in Ashland
Helman House, holiday rental in Ashland
Helman House, holiday rental in Ashland

Helman House

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
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
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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
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Courtside Cottage - WalkScore 93 - Dog Friendly, holiday rental in Ashland
Courtside Cottage - WalkScore 93 - Dog Friendly, holiday rental in Ashland
Courtside Cottage - WalkScore 93 - Dog Friendly, holiday rental in Ashland

Courtside Cottage - WalkScore 93 - Dog Friendly

Holiday Rental House
1 bedroom
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
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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 8
Match: Sleeps
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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
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Downtown Ashland private cottage with garden patio, holiday rental in Ashland
Downtown Ashland private cottage with garden patio, holiday rental in Ashland
Downtown Ashland private cottage with garden patio, holiday rental in Ashland

Downtown Ashland private cottage with garden patio

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Ashland lavender estate. Come stay at our farmhouse!, holiday rental in Ashland
Ashland lavender estate. Come stay at our farmhouse!, holiday rental in Ashland
Ashland lavender estate. Come stay at our farmhouse!, holiday rental in Ashland

Ashland lavender estate. Come stay at our farmhouse!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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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230-Downstairs-Duplex-Private Bathroom-Mountain View, holiday rental in Ashland
230-Downstairs-Duplex-Private Bathroom-Mountain View, holiday rental in Ashland
230-Downstairs-Duplex-Private Bathroom-Mountain View, holiday rental in Ashland

230-Downstairs-Duplex-Private Bathroom-Mountain View

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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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Custom Ashland Home with Fantastic Mountain Views, holiday rental in Ashland
Custom Ashland Home with Fantastic Mountain Views, holiday rental in Ashland
Custom Ashland Home with Fantastic Mountain Views, holiday rental in Ashland

Custom Ashland Home with Fantastic Mountain Views

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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East Main Downtown Bungalow, holiday rental in Ashland
East Main Downtown Bungalow, holiday rental in Ashland
East Main Downtown Bungalow, holiday rental in Ashland

East Main Downtown Bungalow

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

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
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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QuaintStudio Retreat near OSF and DowntownAshland, holiday rental in Ashland
QuaintStudio Retreat near OSF and DowntownAshland, holiday rental in Ashland
QuaintStudio Retreat near OSF and DowntownAshland, holiday rental in Ashland

QuaintStudio Retreat near OSF and DowntownAshland

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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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Country experience close to downtown Ashland, holiday rental in Ashland
Country experience close to downtown Ashland, holiday rental in Ashland
Country experience close to downtown Ashland, holiday rental in Ashland

Country experience close to downtown Ashland

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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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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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Emigrant Creek Guest Lodge on the East Side of Emigrant Lake, 8 miles to Ashland, holiday rental in Ashland
Emigrant Creek Guest Lodge on the East Side of Emigrant Lake, 8 miles to Ashland, holiday rental in Ashland
Emigrant Creek Guest Lodge on the East Side of Emigrant Lake, 8 miles to Ashland, holiday rental in Ashland

Emigrant Creek Guest Lodge on the East Side of Emigrant Lake, 8 miles to Ashland

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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2nd Street Cottages, GARDEN SUITE, holiday rental in Ashland
2nd Street Cottages, GARDEN SUITE, holiday rental in Ashland
2nd Street Cottages, GARDEN SUITE, holiday rental in Ashland

2nd Street Cottages, GARDEN SUITE

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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New Downtown 3 Bedroom Upstairs Flat with views, holiday rental in Ashland
New Downtown 3 Bedroom Upstairs Flat with views, holiday rental in Ashland
New Downtown 3 Bedroom Upstairs Flat with views, holiday rental in Ashland

New Downtown 3 Bedroom Upstairs Flat with views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
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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Country Setting, five minute drive to Ashland close to Emigrant Lake, holiday rental in Ashland
Country Setting, five minute drive to Ashland close to Emigrant Lake, holiday rental in Ashland
Country Setting, five minute drive to Ashland close to Emigrant Lake, holiday rental in Ashland

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

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
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

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Downtown Ashland Earth spa unit with private patio, holiday rental in Ashland
Downtown Ashland Earth spa unit with private patio, holiday rental in Ashland
Downtown Ashland Earth spa unit with private patio, holiday rental in Ashland

Downtown Ashland Earth spa unit with private patio

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Country's Edge Rooms in just outside of Ashland, convenient for travel, holiday rental in Ashland
Country's Edge Rooms in just outside of Ashland, convenient for travel, holiday rental in Ashland
Country's Edge Rooms in just outside of Ashland, convenient for travel, holiday rental in Ashland

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

Holiday Rental House
1 bedroom
0 bathrooms
Sleeps 2
Match: Sleeps
More info
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Lodge Room 2 * GSI&C, holiday rental in Ashland
Lodge Room 2 * GSI&C, holiday rental in Ashland
Lodge Room 2 * GSI&C, holiday rental in Ashland

Lodge Room 2 * GSI&C

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Lodge Room 7 * GSI&C, holiday rental in Ashland
Lodge Room 7 * GSI&C, holiday rental in Ashland
Lodge Room 7 * GSI&C, holiday rental in Ashland

Lodge Room 7 * GSI&C

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Lodge Room 6 * GSI&C, holiday rental in Ashland
Lodge Room 6 * GSI&C, holiday rental in Ashland
Lodge Room 6 * GSI&C, holiday rental in Ashland

Lodge Room 6 * GSI&C

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Lodge Room 1 * GSI&C, holiday rental in Ashland
Lodge Room 1 * GSI&C, holiday rental in Ashland
Lodge Room 1 * GSI&C, holiday rental in Ashland

Lodge Room 1 * GSI&C

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Lodge Room 4 * GSI&C, holiday rental in Ashland
Lodge Room 4 * GSI&C, holiday rental in Ashland
Lodge Room 4 * GSI&C, holiday rental in Ashland

Lodge Room 4 * GSI&C

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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The Indigo Cottage 5 Min walk to Downtown Ashland, holiday rental in Ashland
The Indigo Cottage 5 Min walk to Downtown Ashland, holiday rental in Ashland
The Indigo Cottage 5 Min walk to Downtown Ashland, holiday rental in Ashland

The Indigo Cottage 5 Min walk to Downtown Ashland

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Lodge Room 3 * GSI&C, holiday rental in Ashland
Lodge Room 3 * GSI&C, holiday rental in Ashland
Lodge Room 3 * GSI&C, holiday rental in Ashland

Lodge Room 3 * GSI&C

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Showing results 1-50 of 168
Frequently Asked Questions about Ashland