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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.

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

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Whitetail Waters, vacation rental in Ashland

Whitetail Waters

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Homestead, vacation rental in Ashland

The Homestead

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Madeline Island Lakeside Condo, vacation rental in Ashland

Madeline Island Lakeside Condo

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

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

4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Bayfield- No Cleaning Fees, Charming Newly Remodeled Condo, Gateway to Apostles, vacation rental in Ashland

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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Cabin in the Woods of Madeline Island, vacation rental in Ashland

Cozy Cabin in the Woods of Madeline Island

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

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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Downtown Island Condo, vacation rental in Ashland

Downtown Island Condo

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Luxuriously decorated and designed for large groups or small intimate getaways., vacation rental in Ashland

Luxuriously decorated and designed for large groups or small intimate getaways.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sheila's Downtown Condo on Madeline Island, vacation rental in Ashland

Sheila's Downtown Condo on Madeline Island

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Bell Street-Downtown Oasis, vacation rental in Ashland

Bell Street-Downtown Oasis

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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WEEKDAY DISCOUNTS!! ON GOLF COURSE!!  AIR CONDITIONED!, vacation rental in Ashland

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

3 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
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Bayfield- No Cleaning Fees, Charming Newly Remodeled Condo,  Gateway to Apostles, vacation rental in Ashland

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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Bell Street Lodging-Retreat, vacation rental in Ashland

Bell Street Lodging-Retreat

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Home On 5 Acres With 300 Ft. Of Waterfront!  Surrounded By Forest!, vacation rental in Ashland

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

5 bedrooms
5 bathrooms
Sleeps 24
Match: Sleeps
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Cozy & Quaint studio with fireplace & jacuzzi, vacation rental in Ashland

Cozy & Quaint studio with fireplace & jacuzzi

0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Escape To Madeline Island !  Superior Lakefront 2 Bedroom Condo, vacation rental in Ashland

Escape To Madeline Island ! Superior Lakefront 2 Bedroom Condo

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Bell Street Lodging-Suite, vacation rental in Ashland

Bell Street Lodging-Suite

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Romantic couples retreat, Enjoy the view of Bayfield Harbor, Apostle Islands, vacation rental in Ashland

Romantic couples retreat, Enjoy the view of Bayfield Harbor, Apostle Islands

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful newly renovated Island home, close to town and beaches., vacation rental in Ashland

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

5 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
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Driftwood Cottage: Northern Bayfield County Wisconsin, vacation rental in Ashland

Driftwood Cottage: Northern Bayfield County Wisconsin

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Copper Trout Suite at 250 is the perfect location to for all adventures., vacation rental in Ashland

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Newly Remodeled, well furnished, Lakeside Condo, vacation rental in Ashland

Newly Remodeled, well furnished, Lakeside Condo

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Fresh and Clean, Lakeshore, Remodeled, vacation rental in Ashland

Fresh and Clean, Lakeshore, Remodeled

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Comfortable, Clean, Lakeside, Convenient, vacation rental in Ashland

Comfortable, Clean, Lakeside, Convenient

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beach Front, Deck with view, Clean, vacation rental in Ashland

Beach Front, Deck with view, Clean

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beachfront, Quiet and Comfortable107 Comfortable, Quiet and Convenient, vacation rental in Ashland

Beachfront, Quiet and Comfortable107 Comfortable, Quiet and Convenient

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Salmo House - Salmo Retreat, vacation rental in Ashland

Salmo House - Salmo Retreat

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spectacular Lake Side Location, Cozy Ground Floor Condo, vacation rental in Ashland

Spectacular Lake Side Location, Cozy Ground Floor Condo

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Great location, Clean, Comfortable, Lakeview, Convenient, vacation rental in Ashland

Great location, Clean, Comfortable, Lakeview, Convenient

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Madeline Island Classic Knotty Pine Cabin on Lake Superior, vacation rental in Ashland

Madeline Island Classic Knotty Pine Cabin on Lake Superior

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Fantastic View, Beach Front, Full Kitchen Studio, vacation rental in Ashland

Fantastic View, Beach Front, Full Kitchen Studio

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cute cottage on the golf course, vacation rental in Ashland

Cute cottage on the golf course

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Spectacular Lake Superior Location, vacation rental in Ashland

Spectacular Lake Superior Location

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Salmo Studio - Salmo Retreat, vacation 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, vacation rental in Ashland

7 Pines LaPointe On Madeline Island

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Wonderfully appointed, High Speed Internet, Clean Beach Front Condo, vacation rental in Ashland

Wonderfully appointed, High Speed Internet, Clean Beach Front Condo

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Wonderful Lakefront 3 Bedroom Condo Downtown Bayfield (Bayfield on the Lake), vacation rental in Ashland

Wonderful Lakefront 3 Bedroom Condo Downtown Bayfield (Bayfield on the Lake)

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lakeview, Clean and Very Convenient#109 Quiet and Convenient, Lake Shore Condo, vacation rental in Ashland

Lakeview, Clean and Very Convenient#109 Quiet and Convenient, Lake Shore Condo

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lakeside, Comfortable and Convenient#209 Wonderful New Updates for 2019, vacation rental in Ashland

Lakeside, Comfortable and Convenient#209 Wonderful New Updates for 2019

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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202 Is a Fantastic Beach Front Condo, vacation rental in Ashland

202 Is a Fantastic Beach Front Condo

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Literally Lakeside! Great Location#101 Wonderful Beach Front Location, vacation rental in Ashland

Literally Lakeside! Great Location#101 Wonderful Beach Front Location

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Yoga & Vacation in Bayfield County WI, vacation rental in Ashland

Yoga & Vacation in Bayfield County WI

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Valley Vista, vacation rental in Ashland

Valley Vista

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Enjoy your vacation on a yacht!, vacation 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, vacation 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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Large home on 160 acre Paradise., vacation rental in Ashland

Large home on 160 acre Paradise.

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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