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Holiday Homes in Ashland

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121 rentals in Ashland.
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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

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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The Terra Cottage Inn a beautiful Luxury Apartment, holiday rental in Ashland

The Terra Cottage Inn a beautiful Luxury Apartment

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hyatt Prairie Mountain Cabin, holiday rental in Ashland

Hyatt Prairie Mountain Cabin

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Ashland Cottage, walk to town, holiday rental in Ashland

The Ashland Cottage, walk to town

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Whispering Pines Cabin Retreat ~ Dog Friendly, holiday rental in Ashland

Whispering Pines Cabin Retreat ~ Dog Friendly

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Craftsman Style Home In Country Setting, holiday rental in Ashland

Craftsman Style Home In Country Setting

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Hanna's House- Your Home Away from Home, holiday rental in Ashland

Hanna's House- Your Home Away from Home

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stacy's 2nd St Cottages .. Steps to theaters, Lithia Park and downtown Ashland, holiday rental in Ashland

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Madrone House, New Country Getaway with Panoramic Views, holiday rental in Ashland

The Madrone House, New Country Getaway with Panoramic Views

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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~AGC~ Oberon 4 Blocks 2 Downtown - Charming Cozy Private Stylish Shakespeare OSF, holiday rental in Ashland

~AGC~ Oberon 4 Blocks 2 Downtown - Charming Cozy Private Stylish Shakespeare OSF

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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~AGC~- Carriage House -Best Location - 2bd/2bth -4 Blocks 2 Town, Lithia & ~OSF~, holiday rental in Ashland

~AGC~- Carriage House -Best Location - 2bd/2bth -4 Blocks 2 Town, Lithia & ~OSF~

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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'Orchard Suite'  Stay...Relax...Enjoy, holiday rental in Ashland

'Orchard Suite' Stay...Relax...Enjoy

1 bedroom
1 bathroom
Sleeps 7
Match: Sleeps
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The Ridgeview Lodge ~ Perfect for Family Events, Sleeps 15, Beautiful Views, holiday rental in Ashland

The Ridgeview Lodge ~ Perfect for Family Events, Sleeps 15, Beautiful Views

3 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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ArtYcottage  UNBELIEVEABLE..., holiday rental in Ashland

ArtYcottage UNBELIEVEABLE...

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Maple Apartment at Tudor House Vacation Rentals, holiday rental in Ashland

The Maple Apartment at Tudor House Vacation Rentals

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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~AGC~-Romeo & Juliet - 4 Blocks to Downtown, Lithia Park & ~OSF~ Best Location, holiday rental in Ashland

~AGC~-Romeo & Juliet - 4 Blocks to Downtown, Lithia Park & ~OSF~ Best Location

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hyatt Lake Mountain Retreat, holiday rental in Ashland

Hyatt Lake Mountain Retreat

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Winter on PINE STREET!  ASHLAND! COZY cottage near Lithia Park and Town!, holiday rental in Ashland

Winter on PINE STREET! ASHLAND! COZY cottage near Lithia Park and Town!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Loft at Brenden House with private deck, kitchen, WIFI, A/C and parking., holiday rental in Ashland

The Loft at Brenden House with private deck, kitchen, WIFI, A/C and parking.

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Dogwood Suite at Tudor House Vacation Rentals, holiday rental in Ashland

The Dogwood Suite at Tudor House Vacation Rentals

1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
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Private Suite Near Shakespeare, holiday rental in Ashland

Private Suite Near Shakespeare

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming, Comfortable Garden Studio Above The University., holiday rental in Ashland

Charming, Comfortable Garden Studio Above The University.

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Magnificent, secluded, garden, private decks for families and pets., holiday rental in Ashland

Magnificent, secluded, garden, private decks for families and pets.

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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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!

6 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Quiet and peaceful cottage close to downtown, holiday rental in Ashland

Quiet and peaceful cottage close to downtown

1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
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The High Street Cottage An Artists' Garden Cottage, holiday rental in Ashland

The High Street Cottage An Artists' Garden Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hyatt Praire Mountain Cabin, holiday rental in Ashland

Hyatt Praire Mountain Cabin

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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De Launay House, holiday rental in Ashland

De Launay House

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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2nd Street Cottages, HERITAGE HOUSE, holiday rental in Ashland

2nd Street Cottages, HERITAGE HOUSE

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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2nd Street Cottages, GARDEN SUITE, holiday rental in Ashland

2nd Street Cottages, GARDEN SUITE

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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#33 The Cabins at Hyatt Lake - Sleeps 6 - Hot Tub, holiday rental in Ashland

#33 The Cabins at Hyatt Lake - Sleeps 6 - Hot Tub

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stay Ashland like never before.  Explore days, campfire stars at night!, holiday rental in Ashland

Stay Ashland like never before. Explore days, campfire stars at night!

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Perfect vacation cottage, holiday rental in Ashland

Perfect vacation cottage

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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#46 The Cabins at Hyatt Lake-Sleeps 5-Dog Friendly, holiday rental in Ashland

#46 The Cabins at Hyatt Lake-Sleeps 5-Dog Friendly

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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#52 The Cabins at Hyatt Lake - Sleeps 4 -Lake View - Hot Tub, holiday rental in Ashland

#52 The Cabins at Hyatt Lake - Sleeps 4 -Lake View - Hot Tub

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Pelton Villa, holiday rental in Ashland

Pelton Villa

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ashland Lodge w/ Lake Views, Patio & 5 Mtn Bikes!, holiday rental in Ashland

Ashland Lodge w/ Lake Views, Patio & 5 Mtn Bikes!

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Brenden House, Walk to Theaters, holiday rental in Ashland

The Brenden House, Walk to Theaters

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cattle View Ranch House, holiday rental in Ashland

Cattle View Ranch House

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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The Pioneer House -North Suite (Upstairs) - Closest to OSF!, holiday rental in Ashland

The Pioneer House -North Suite (Upstairs) - Closest to OSF!

2 bedrooms
1 bathroom
Sleeps 6
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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Luxurious Home near Downtown Ashland and Theaters, holiday rental in Ashland

Luxurious Home near Downtown Ashland and Theaters

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful Apartment in Ashland, holiday rental in Ashland

Beautiful Apartment in Ashland

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Aloha House ~ Hot Tub & Seasonal Pool, holiday rental in Ashland

The Aloha House ~ Hot Tub & Seasonal Pool

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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#32 The Cabins at Hyatt Lake - Sleeps 6 - Hot Tub, holiday rental in Ashland

#32 The Cabins at Hyatt Lake - Sleeps 6 - Hot Tub

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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#1B Soda Mountain ~ Green Springs Cabins ~  Jacuzzi Tub, holiday rental in Ashland

#1B Soda Mountain ~ Green Springs Cabins ~ Jacuzzi Tub

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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#1D Hobart Peak ~ Green Springs Cabins ~  Jacuzzi Tub, holiday rental in Ashland

#1D Hobart Peak ~ Green Springs Cabins ~ Jacuzzi Tub

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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#32 & #33 Hyatt Lake Compound - Sleeps 12, holiday rental in Ashland

#32 & #33 Hyatt Lake Compound - Sleeps 12

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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