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Ashland Vacation Rentals

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50 rentals in Ashland.
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River Rock Cottage Is Located On The Shore Of Lake Superior On Chequamegon Bay., vacation rental in Ashland
River Rock Cottage Is Located On The Shore Of Lake Superior On Chequamegon Bay., vacation rental in Ashland
River Rock Cottage Is Located On The Shore Of Lake Superior On Chequamegon Bay., vacation rental in Ashland

River Rock Cottage Is Located On The Shore Of Lake Superior On Chequamegon Bay.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails., vacation rental in Ashland
Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails., vacation rental in Ashland
Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails., vacation rental in Ashland

Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Relax on the shores of Lake Superior, vacation rental in Ashland
Relax on the shores of Lake Superior, vacation rental in Ashland
Relax on the shores of Lake Superior, vacation rental in Ashland

Relax on the shores of Lake Superior

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The PERFECT Beachside Getaway, vacation rental in Ashland
The PERFECT Beachside Getaway, vacation rental in Ashland
The PERFECT Beachside Getaway, vacation rental in Ashland

The PERFECT Beachside Getaway

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Adventure Awaits on the Shores of Lake Superior, vacation rental in Ashland
Adventure Awaits on the Shores of Lake Superior, vacation rental in Ashland
Adventure Awaits on the Shores of Lake Superior, vacation rental in Ashland

Adventure Awaits on the Shores of Lake Superior

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Homestead, vacation rental in Ashland
The Homestead, vacation rental in Ashland
The Homestead, vacation rental in Ashland

The Homestead

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Whitetail Waters, vacation rental in Ashland
Whitetail Waters, vacation rental in Ashland
Whitetail Waters, vacation rental in Ashland

Whitetail Waters

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Ashland Apartment: Walkable & Pet Friendly!, vacation rental in Ashland
NEW! Ashland Apartment: Walkable & Pet Friendly!, vacation rental in Ashland
NEW! Ashland Apartment: Walkable & Pet Friendly!, vacation rental in Ashland

NEW! Ashland Apartment: Walkable & Pet Friendly!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Breathtaking family getaway on the beach (pet friendly!), vacation rental in Ashland
Breathtaking family getaway on the beach (pet friendly!), vacation rental in Ashland
Breathtaking family getaway on the beach (pet friendly!), vacation rental in Ashland

Breathtaking family getaway on the beach (pet friendly!)

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Escape to this private retreat with panoramic views of Lake Superior, vacation rental in Ashland
Escape to this private retreat with panoramic views of Lake Superior, vacation rental in Ashland
Escape to this private retreat with panoramic views of Lake Superior, vacation rental in Ashland

Escape to this private retreat with panoramic views of Lake Superior

Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Farmstead Retreat with woods, pond, trails and easy access to local attractions, vacation rental in Ashland
Farmstead Retreat with woods, pond, trails and easy access to local attractions, vacation rental in Ashland
Farmstead Retreat with woods, pond, trails and easy access to local attractions, vacation rental in Ashland

Farmstead Retreat with woods, pond, trails and easy access to local attractions

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Madeline Island Lakeside Condo, vacation rental in Ashland
Madeline Island Lakeside Condo, vacation rental in Ashland
Madeline Island Lakeside Condo, vacation rental in Ashland

Madeline Island Lakeside Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Cabin with Majestic View, Close to Town, vacation rental in Ashland
Cozy Cabin with Majestic View, Close to Town, vacation rental in Ashland
Cozy Cabin with Majestic View, Close to Town, vacation rental in Ashland

Cozy Cabin with Majestic View, Close to Town

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lake Superior Beachfront, 4+ Bedrooms, Spectacular Timberframe Home, vacation rental in Ashland
Lake Superior Beachfront, 4+ Bedrooms, Spectacular Timberframe Home, vacation rental in Ashland
Lake Superior Beachfront, 4+ Bedrooms, Spectacular Timberframe Home, vacation rental in Ashland

Lake Superior Beachfront, 4+ Bedrooms, Spectacular Timberframe Home

Rental Home
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Gorgeous Chalet on Lake Superior with Private Sandy Beach!, vacation rental in Ashland
Gorgeous Chalet on Lake Superior with Private Sandy Beach!, vacation rental in Ashland
Gorgeous Chalet on Lake Superior with Private Sandy Beach!, vacation rental in Ashland

Gorgeous Chalet on Lake Superior with Private Sandy Beach!

Rental Home
4 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
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Bell Street-Downtown Oasis, vacation rental in Ashland
Bell Street-Downtown Oasis, vacation rental in Ashland
Bell Street-Downtown Oasis, vacation rental in Ashland

Bell Street-Downtown Oasis

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful  home on the golf course on Madeline island
3 bedrooms 8 beds, vacation rental in Ashland
Beautiful  home on the golf course on Madeline island
3 bedrooms 8 beds, vacation rental in Ashland
Beautiful  home on the golf course on Madeline island
3 bedrooms 8 beds, vacation rental in Ashland

Beautiful home on the golf course on Madeline island 3 bedrooms 8 beds

Rental Home
3 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
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Valley Vista- 3 Bed Cabin in Valhalla Hills. 2 NIGHT MINIMUM WINTER SPECIAL, vacation rental in Ashland
Valley Vista- 3 Bed Cabin in Valhalla Hills. 2 NIGHT MINIMUM WINTER SPECIAL, vacation rental in Ashland
Valley Vista- 3 Bed Cabin in Valhalla Hills. 2 NIGHT MINIMUM WINTER SPECIAL, vacation rental in Ashland

Valley Vista- 3 Bed Cabin in Valhalla Hills. 2 NIGHT MINIMUM WINTER SPECIAL

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious Lake Superior Estate with Outdoor Hot Tub, vacation rental in Ashland
Luxurious Lake Superior Estate with Outdoor Hot Tub, vacation rental in Ashland
Luxurious Lake Superior Estate with Outdoor Hot Tub, vacation rental in Ashland

Luxurious Lake Superior Estate with Outdoor Hot Tub

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Entire Cozy  Cottage on Bayfield Peninsula, vacation rental in Ashland
Entire Cozy  Cottage on Bayfield Peninsula, vacation rental in Ashland
Entire Cozy  Cottage on Bayfield Peninsula, vacation rental in Ashland

Entire Cozy Cottage on Bayfield Peninsula

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cute cottage on the golf course, vacation rental in Ashland
Cute cottage on the golf course, vacation rental in Ashland
Cute cottage on the golf course, vacation rental in Ashland

Cute cottage on the golf course

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Salmo House - Salmo Retreat, vacation rental in Ashland
Salmo House - Salmo Retreat, vacation rental in Ashland
Salmo House - Salmo Retreat, vacation rental in Ashland

Salmo House - Salmo Retreat

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Washburn Beach House Sleeps 6, Private Beach, 11.6 Miles from Bayfield!, vacation rental in Ashland
Washburn Beach House Sleeps 6, Private Beach, 11.6 Miles from Bayfield!, vacation rental in Ashland
Washburn Beach House Sleeps 6, Private Beach, 11.6 Miles from Bayfield!, vacation rental in Ashland

Washburn Beach House Sleeps 6, Private Beach, 11.6 Miles from Bayfield!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Eagle Moon - Unique 8 sided Home Nestled in the Woods Pet Friendly!, vacation rental in Ashland
Eagle Moon - Unique 8 sided Home Nestled in the Woods Pet Friendly!, vacation rental in Ashland
Eagle Moon - Unique 8 sided Home Nestled in the Woods Pet Friendly!, vacation rental in Ashland

Eagle Moon - Unique 8 sided Home Nestled in the Woods Pet Friendly!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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7 Pines LaPointe On Madeline Island, vacation rental in Ashland
7 Pines LaPointe On Madeline Island, vacation rental in Ashland
7 Pines LaPointe On Madeline Island, vacation rental in Ashland

7 Pines LaPointe On Madeline Island

Cabin
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Payne Cottage - Unique Private Lake Access Home with a Loft, vacation rental in Ashland
Payne Cottage - Unique Private Lake Access Home with a Loft, vacation rental in Ashland
Payne Cottage - Unique Private Lake Access Home with a Loft, vacation rental in Ashland

Payne Cottage - Unique Private Lake Access Home with a Loft

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Parkside Condo 6 - 2 Bedrooms 2 Baths, vacation rental in Ashland
Parkside Condo 6 - 2 Bedrooms 2 Baths, vacation rental in Ashland
Parkside Condo 6 - 2 Bedrooms 2 Baths, vacation rental in Ashland

Parkside Condo 6 - 2 Bedrooms 2 Baths

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Salmo Studio - Salmo Retreat, vacation rental in Ashland
Salmo Studio - Salmo Retreat, vacation rental in Ashland
Salmo Studio - Salmo Retreat, vacation rental in Ashland

Salmo Studio - Salmo Retreat

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious four bedroom house -walking distance to Lake Superior / Washburn shops, vacation rental in Ashland
Spacious four bedroom house -walking distance to Lake Superior / Washburn shops, vacation rental in Ashland
Spacious four bedroom house -walking distance to Lake Superior / Washburn shops, vacation rental in Ashland

Spacious four bedroom house -walking distance to Lake Superior / Washburn shops

Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Cedar Log Cabin - Wonderful Family Cabin located on the Robert Trent Jones Golf, vacation rental in Ashland
Cedar Log Cabin - Wonderful Family Cabin located on the Robert Trent Jones Golf, vacation rental in Ashland
Cedar Log Cabin - Wonderful Family Cabin located on the Robert Trent Jones Golf, vacation rental in Ashland

Cedar Log Cabin - Wonderful Family Cabin located on the Robert Trent Jones Golf

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Unique Family Home on Golf Course, vacation rental in Ashland
Unique Family Home on Golf Course, vacation rental in Ashland
Unique Family Home on Golf Course, vacation rental in Ashland

Unique Family Home on Golf Course

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Pines Cabin - Wonderful Sunsets and Lake Superior Access!, vacation rental in Ashland
Cozy Pines Cabin - Wonderful Sunsets and Lake Superior Access!, vacation rental in Ashland
Cozy Pines Cabin - Wonderful Sunsets and Lake Superior Access!, vacation rental in Ashland

Cozy Pines Cabin - Wonderful Sunsets and Lake Superior Access!

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront Condo A Few Steps to Lake Superior, vacation rental in Ashland
Lakefront Condo A Few Steps to Lake Superior, vacation rental in Ashland
Lakefront Condo A Few Steps to Lake Superior, vacation rental in Ashland

Lakefront Condo A Few Steps to Lake Superior

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Yoga & Vacation in Bayfield County WI, vacation rental in Ashland
Yoga & Vacation in Bayfield County WI, vacation rental in Ashland
Yoga & Vacation in Bayfield County WI, vacation rental in Ashland

Yoga & Vacation in Bayfield County WI

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Parkside Condo 7 - 2 Bedrooms 2.5 Baths, vacation rental in Ashland
Parkside Condo 7 - 2 Bedrooms 2.5 Baths, vacation rental in Ashland
Parkside Condo 7 - 2 Bedrooms 2.5 Baths, vacation rental in Ashland

Parkside Condo 7 - 2 Bedrooms 2.5 Baths

Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
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Sunset View - 3 Bedroom 2.5 Home with Guest House, vacation rental in Ashland
Sunset View - 3 Bedroom 2.5 Home with Guest House, vacation rental in Ashland
Sunset View - 3 Bedroom 2.5 Home with Guest House, vacation rental in Ashland

Sunset View - 3 Bedroom 2.5 Home with Guest House

Rental Home
6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Remodeled Downtown Condo, vacation rental in Ashland
Remodeled Downtown Condo, vacation rental in Ashland
Remodeled Downtown Condo, vacation rental in Ashland

Remodeled Downtown Condo

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Quaint updated apartment overlooking the Bay, vacation rental in Ashland
Quaint updated apartment overlooking the Bay, vacation rental in Ashland
Quaint updated apartment overlooking the Bay, vacation rental in Ashland

Quaint updated apartment overlooking the Bay

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Updated Suite in great location close to Bayfield, the Apostle Islands, and more, vacation rental in Ashland
Updated Suite in great location close to Bayfield, the Apostle Islands, and more, vacation rental in Ashland
Updated Suite in great location close to Bayfield, the Apostle Islands, and more, vacation rental in Ashland

Updated Suite in great location close to Bayfield, the Apostle Islands, and more

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Peaceful 3+ Bedroom Home w/ SAUNA,  Big Field/firepit, Ravine Garden Patio,, vacation rental in Ashland
Peaceful 3+ Bedroom Home w/ SAUNA,  Big Field/firepit, Ravine Garden Patio,, vacation rental in Ashland
Peaceful 3+ Bedroom Home w/ SAUNA,  Big Field/firepit, Ravine Garden Patio,, vacation rental in Ashland

Peaceful 3+ Bedroom Home w/ SAUNA, Big Field/firepit, Ravine Garden Patio,

Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Slainte - 3 Bedroom 3 Bathroom Cottage, vacation rental in Ashland
Slainte - 3 Bedroom 3 Bathroom Cottage, vacation rental in Ashland
Slainte - 3 Bedroom 3 Bathroom Cottage, vacation rental in Ashland

Slainte - 3 Bedroom 3 Bathroom Cottage

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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La Sirena - 2 Bedroom 2 Bath Cottage, vacation rental in Ashland
La Sirena - 2 Bedroom 2 Bath Cottage, vacation rental in Ashland
La Sirena - 2 Bedroom 2 Bath Cottage, vacation rental in Ashland

La Sirena - 2 Bedroom 2 Bath Cottage

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Quaint updated apartment overlooking the Bay, vacation rental in Ashland
Quaint updated apartment overlooking the Bay, vacation rental in Ashland
Quaint updated apartment overlooking the Bay, vacation rental in Ashland

Quaint updated apartment overlooking the Bay

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Bayfield Farmhouse Sleeps 16 - 4 bdrm/2 baths king, vacation rental in Ashland
Bayfield Farmhouse Sleeps 16 - 4 bdrm/2 baths king, vacation rental in Ashland
Bayfield Farmhouse Sleeps 16 - 4 bdrm/2 baths king, vacation rental in Ashland

Bayfield Farmhouse Sleeps 16 - 4 bdrm/2 baths king

Rental Home
5 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
More info
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Stately Home in Washburn WI. Walking distance to Chequamegon Bay, Lake Superior, vacation rental in Ashland
Stately Home in Washburn WI. Walking distance to Chequamegon Bay, Lake Superior, vacation rental in Ashland
Stately Home in Washburn WI. Walking distance to Chequamegon Bay, Lake Superior, vacation rental in Ashland

Stately Home in Washburn WI. Walking distance to Chequamegon Bay, Lake Superior

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Comfortable suite, great location, easy access to Lake Superior!, vacation rental in Ashland
Comfortable suite, great location, easy access to Lake Superior!, vacation rental in Ashland
Comfortable suite, great location, easy access to Lake Superior!, vacation rental in Ashland

Comfortable suite, great location, easy access to Lake Superior!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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The Boathouse Lodge on Madeline Island, vacation rental in Ashland
The Boathouse Lodge on Madeline Island, vacation rental in Ashland
The Boathouse Lodge on Madeline Island, vacation rental in Ashland

The Boathouse Lodge on Madeline Island

Rental Home
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Newly Renovated House on Lake Superior with Private Beach, vacation rental in Ashland
Newly Renovated House on Lake Superior with Private Beach, vacation rental in Ashland
Newly Renovated House on Lake Superior with Private Beach, vacation rental in Ashland

Newly Renovated House on Lake Superior with Private Beach

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Spacious townhome on Madeline Island Golf Course, vacation rental in Ashland
Spacious townhome on Madeline Island Golf Course, vacation rental in Ashland
Spacious townhome on Madeline Island Golf Course, vacation rental in Ashland

Spacious townhome on Madeline Island Golf Course

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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