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Holiday Homes in Ashland

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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., holiday rental in Ashland

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

4 bedrooms
2 bathrooms
Sleeps 14
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Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior, holiday rental in Ashland

Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior

2 bedrooms
1 bathroom
Sleeps 6
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Whitetail Waters, holiday rental in Ashland

Whitetail Waters

3 bedrooms
2 bathrooms
Sleeps 8
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The Homestead, holiday rental in Ashland

The Homestead

1 bedroom
1 bathroom
Sleeps 4
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Madeline Island Lakeside Condo, holiday rental in Ashland

Madeline Island Lakeside Condo

2 bedrooms
2 bathrooms
Sleeps 8
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Lake Superior Beachfront, 4+ Bedrooms, Spectacular Timberframe Home, holiday rental in Ashland

Lake Superior Beachfront, 4+ Bedrooms, Spectacular Timberframe Home

4 bedrooms
4 bathrooms
Sleeps 9
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Cozy Cabin with Majestic View, Close to Town, holiday rental in Ashland

Cozy Cabin with Majestic View, Close to Town

2 bedrooms
1 bathroom
Sleeps 4
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Bayfield- No Cleaning Fees, Charming Newly Remodeled Condo, Gateway to Apostles, holiday rental in Ashland

Bayfield- No Cleaning Fees, Charming Newly Remodeled Condo, Gateway to Apostles

1 bedroom
1 bathroom
Sleeps 4
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Bayfield- No Cleaning Fees, Charming Condo, Jumping Off Point to Apostles, holiday rental in Ashland

Bayfield- No Cleaning Fees, Charming Condo, Jumping Off Point to Apostles

1 bedroom
1 bathroom
Sleeps 4
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Downtown Island Condo, holiday rental in Ashland

Downtown Island Condo

1 bedroom
1 bathroom
Sleeps 4
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Sheila's Downtown Condo on Madeline Island, holiday rental in Ashland

Sheila's Downtown Condo on Madeline Island

1 bedroom
1 bathroom
Sleeps 4
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Bell Street-Downtown Oasis, holiday rental in Ashland

Bell Street-Downtown Oasis

2 bedrooms
1 bathroom
Sleeps 6
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Bayfield- No Cleaning Fees, Charming Newly Remodeled Condo,  Gateway to Apostles, holiday rental in Ashland

Bayfield- No Cleaning Fees, Charming Newly Remodeled Condo, Gateway to Apostles

1 bedroom
1 bathroom
Sleeps 4
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WEEKDAY DISCOUNTS!! ON GOLF COURSE!!  AIR CONDITIONED!, holiday rental in Ashland

WEEKDAY DISCOUNTS!! ON GOLF COURSE!! AIR CONDITIONED!

3 bedrooms
2 bathrooms
Sleeps 16
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Madeline Island cottage within steps of Lake Superior, holiday rental in Ashland

Madeline Island cottage within steps of Lake Superior

2 bedrooms
1 bathroom
Sleeps 6
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Cozy & Quaint studio with fireplace & jacuzzi, holiday rental in Ashland

Cozy & Quaint studio with fireplace & jacuzzi

0 bedrooms
1 bathroom
Sleeps 3
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Bell Street Lodging-Retreat, holiday rental in Ashland

Bell Street Lodging-Retreat

4 bedrooms
2 bathrooms
Sleeps 10
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4 Islands View from this spectacular property, holiday rental in Ashland

4 Islands View from this spectacular property

4 bedrooms
3 bathrooms
Sleeps 8
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Beautiful Home On 5 Acres With 300 Ft. Of Waterfront!  Surrounded By Forest!, holiday rental in Ashland

Beautiful Home On 5 Acres With 300 Ft. Of Waterfront! Surrounded By Forest!

5 bedrooms
5 bathrooms
Sleeps 24
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Beautiful newly renovated Island home, close to town and beaches., holiday rental in Ashland

Beautiful newly renovated Island home, close to town and beaches.

5 bedrooms
2 bathrooms
Sleeps 16
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Escape To Madeline Island !  Superior Lakefront 2 Bedroom Condo, holiday rental in Ashland

Escape To Madeline Island ! Superior Lakefront 2 Bedroom Condo

2 bedrooms
1 bathroom
Sleeps 4
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Driftwood Cottage: Northern Bayfield County Wisconsin, holiday rental in Ashland

Driftwood Cottage: Northern Bayfield County Wisconsin

3 bedrooms
2 bathrooms
Sleeps 6
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Salmo House - Salmo Retreat, holiday rental in Ashland

Salmo House - Salmo Retreat

1 bedroom
1 bathroom
Sleeps 4
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Cute cottage on the golf course, holiday rental in Ashland

Cute cottage on the golf course

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Copper Trout Suite at 250 is the perfect location to for all adventures., holiday rental in Ashland

The Copper Trout Suite at 250 is the perfect location to for all adventures.

2 bedrooms
2 bathrooms
Sleeps 4
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Library Street Cottage, holiday rental in Ashland

Library Street Cottage

2 bedrooms
1 bathroom
Sleeps 4
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Harbor View Tourist Room: Lower Level - Harbor View Tourist Room: Walk out Lower, holiday rental in Ashland

Harbor View Tourist Room: Lower Level - Harbor View Tourist Room: Walk out Lower

1 bedroom
1 bathroom
Sleeps 4
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2 bedroom accommodation in La Pointe, holiday rental in Ashland

2 bedroom accommodation in La Pointe

2 bedrooms
1 bathroom
Sleeps 4
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Madeline Island Classic Knotty Pine Cabin on Lake Superior, holiday rental in Ashland

Madeline Island Classic Knotty Pine Cabin on Lake Superior

5 bedrooms
3 bathrooms
Sleeps 10
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Suite Two at La Pointe Lodging  Suite Two La Pointe Lodging - Motel Style Suite, holiday rental in Ashland

Suite Two at La Pointe Lodging Suite Two La Pointe Lodging - Motel Style Suite

1 bedroom
1 bathroom
Sleeps 2
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Uptown Flat - Steeple Hill Flats, holiday rental in Ashland

Uptown Flat - Steeple Hill Flats

1 bedroom
1 bathroom
Sleeps 2
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5 bedroom accommodation in La Pointe, holiday rental in Ashland

5 bedroom accommodation in La Pointe

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Bungalow on Broad - Bungalow on Broad: Living Large in Downtown Bayfield, holiday rental in Ashland

Bungalow on Broad - Bungalow on Broad: Living Large in Downtown Bayfield

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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3 bedroom accommodation in La Pointe, holiday rental in Ashland

3 bedroom accommodation in La Pointe

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2 bedroom accommodation in La Pointe, holiday rental in Ashland

2 bedroom accommodation in La Pointe

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Suite One at La Pointe Lodging, holiday rental in Ashland

Suite One at La Pointe Lodging

1 bedroom
1 bathroom
Sleeps 2
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3 bedroom accommodation in La Pointe, holiday rental in Ashland

3 bedroom accommodation in La Pointe

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Salmo Studio - Salmo Retreat, holiday rental in Ashland

Salmo Studio - Salmo Retreat

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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7 Pines LaPointe On Madeline Island, holiday rental in Ashland

7 Pines LaPointe On Madeline Island

1 bedroom
2 bathrooms
Sleeps 6
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2 bedroom accommodation in La Pointe, holiday rental in Ashland

2 bedroom accommodation in La Pointe

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Haven House on Madeline Island, holiday rental in Ashland

Haven House on Madeline Island

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Wonderful Family Cabin, holiday rental in Ashland

Wonderful Family Cabin

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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2 bedroom accommodation in La Pointe, holiday rental in Ashland

2 bedroom accommodation in La Pointe

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Large home on 160 acre Paradise., holiday rental in Ashland

Large home on 160 acre Paradise.

5 bedrooms
2 bathrooms
Sleeps 12
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2 bedroom accommodation in La Pointe, holiday rental in Ashland

2 bedroom accommodation in La Pointe

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2 bedroom accommodation in La Pointe, holiday rental in Ashland

2 bedroom accommodation in La Pointe

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Yoga & Vacation in Bayfield County WI, holiday rental in Ashland

Yoga & Vacation in Bayfield County WI

2 bedrooms
1 bathroom
Sleeps 5
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Valley Vista, holiday rental in Ashland

Valley Vista

3 bedrooms
2 bathrooms
Sleeps 8
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Enjoy your vacation on a yacht!, holiday rental in Ashland

Enjoy your vacation on a yacht!

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Blue Vista Farmhouse - Blue Vista Farmhouse | Private Home on 40 Acre Berry Farm, holiday rental in Ashland

Blue Vista Farmhouse - Blue Vista Farmhouse | Private Home on 40 Acre Berry Farm

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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