Vacation rentals in Chequamegon Bay, WI

49 available vacation rental offers

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Best vacation rentals and Airbnb offers in Chequamegon Bay, WI

Second Wind Country Inn - Chequamegon Bay, WI

Second Wind Country Inn

Guest House, Chequamegon Bay

Second Wind Country Inn is a guest house in Chequamegon Bay, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Second Wind Country Inn

Second Wind Country Inn is a guest house in Chequamegon Bay, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, free parking, and ac.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,683.

From$215/night
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Bell Street Lodging-Suite - Chequamegon Bay, WI

Bell Street Lodging-Suite

Apartment, Chequamegon Bay

Bell Street Lodging-Suite is a apartment in Chequamegon Bay. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Bell Street Lodging-Suite

Bell Street Lodging-Suite is a apartment in Chequamegon Bay. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, ac, air conditioning, and heating.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,528.

From$218/night
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Upper level, one bedroom, one bath condo, with Lake Superior views. - Chequamegon Bay, WI

Upper level, one bedroom, one bath condo, with Lake Superior views.

Condo, Chequamegon Bay

Upper level, one bedroom, one bath condo, with Lake Superior views. is a condo in Chequamegon Bay, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Upper level, one bedroom, one bath condo, with Lake Superior views.

Upper level, one bedroom, one bath condo, with Lake Superior views. is a condo in Chequamegon Bay, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,638.

From$234/night
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Snowmobile, Ski, or ATV Direct from This Cozy Cabin! - Chequamegon Bay, WI

Snowmobile, Ski, or ATV Direct from This Cozy Cabin!

Cabin, Chequamegon Bay

Snowmobile, Ski, or ATV Direct from This Cozy Cabin! is a cabin in Chequamegon Bay, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Snowmobile, Ski, or ATV Direct from This Cozy Cabin!

Snowmobile, Ski, or ATV Direct from This Cozy Cabin! is a cabin in Chequamegon Bay, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,661.

From$237/night
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Waterfront vacation rentals in Chequamegon Bay, WI

Discover vacation rentals close to the coast, water, and beach areas around Chequamegon Bay, WI.

Harborside Condo | Bayfield Lake Superior - Chequamegon Bay, WI

Harborside Condo | Bayfield Lake Superior

Condo, Chequamegon Bay

Harborside Condo · Bayfield Lake Superior is a condo in Chequamegon Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Harborside Condo | Bayfield Lake Superior

Harborside Condo · Bayfield Lake Superior is a condo in Chequamegon Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,326.

From$332/night
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Bayfield Oasis: Stunning Lake Superior views within walking distance to town! - Chequamegon Bay, WI

Bayfield Oasis: Stunning Lake Superior views within walking distance to town!

Holiday Home, Chequamegon Bay

Bayfield Oasis: Stunning Lake Superior views within walking distance to town! is a holiday home in Chequamegon Bay, with easy beach access and parking. This stay gives travelers a…

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About Bayfield Oasis: Stunning Lake Superior views within walking distance to town!

Bayfield Oasis: Stunning Lake Superior views within walking distance to town! is a holiday home in Chequamegon Bay, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, parking, free parking, ac, and air conditioning.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,482.

From$355/night
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Walk to Lake Superior from this 4B/2b house in Washburn's Historic District. . - Chequamegon Bay, WI

Walk to Lake Superior from this 4B/2b house in Washburn's Historic District. .

Holiday Home, Chequamegon Bay

Walk to Lake Superior from this 4B/2b house in Washburn's Historic District. . is a holiday home in Chequamegon Bay, with parking and kitchen access. This stay gives travelers a comfortable…

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About Walk to Lake Superior from this 4B/2b house in Washburn's Historic District. .

Walk to Lake Superior from this 4B/2b house in Washburn's Historic District. . is a holiday home in Chequamegon Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,740.

From$391/night
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The Cozy Nook in beautiful Bayfield, Wisconsin, stay awhile... - Chequamegon Bay, WI

The Cozy Nook in beautiful Bayfield, Wisconsin, stay awhile...

B & B, Chequamegon Bay

The Cozy Nook in beautiful Bayfield, Wisconsin, stay awhile... is a b & b in Chequamegon Bay, with easy beach access. This stay gives travelers a comfortable base for exploring the area,…

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About The Cozy Nook in beautiful Bayfield, Wisconsin, stay awhile...

The Cozy Nook in beautiful Bayfield, Wisconsin, stay awhile... is a b & b in Chequamegon Bay, with easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: washer, dryer, ac, and air conditioning.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,250.

From$321/night
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Family-friendly vacation rentals in Chequamegon Bay, WI

Plan a trip with stays that give families more room to spread out.

3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit - Chequamegon Bay, WI

3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

Holiday Home, Chequamegon Bay

3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit is a holiday home in Chequamegon Bay, with pet-friendly space, outdoor space, and kitchen access. This stay gives…

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About 3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit is a holiday home in Chequamegon Bay, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,992.

From$427/night
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Johnston`s Golf Cottage - Madeline Island Golf Retreat Close to Town - Chequamegon Bay, WI

Johnston`s Golf Cottage - Madeline Island Golf Retreat Close to Town

Cabin, Chequamegon Bay

Johnston`s Golf Cottage - Madeline Island Golf Retreat Close to Town is a cabin in Chequamegon Bay, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About Johnston`s Golf Cottage - Madeline Island Golf Retreat Close to Town

Johnston`s Golf Cottage - Madeline Island Golf Retreat Close to Town is a cabin in Chequamegon Bay, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $3,019.

From$431/night
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Slainte - Cottage located near Downtown La Pointe with Screened-in Porch! - Chequamegon Bay, WI

Slainte - Cottage located near Downtown La Pointe with Screened-in Porch!

Holiday Home, Chequamegon Bay

Slainte - Cottage located near Downtown La Pointe with Screened-in Porch! is a holiday home in Chequamegon Bay, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Slainte - Cottage located near Downtown La Pointe with Screened-in Porch!

Slainte - Cottage located near Downtown La Pointe with Screened-in Porch! is a holiday home in Chequamegon Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $3,897.

From$557/night
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Madeline Island cottage -just steps of Lake Superior with sweeping views. - Chequamegon Bay, WI

Madeline Island cottage -just steps of Lake Superior with sweeping views.

Cottage, Chequamegon Bay

Madeline Island cottage -just steps of Lake Superior with sweeping views. is a cottage in Chequamegon Bay, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Madeline Island cottage -just steps of Lake Superior with sweeping views.

Madeline Island cottage -just steps of Lake Superior with sweeping views. is a cottage in Chequamegon Bay, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $4,169.

From$596/night
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Pet-friendly vacation rentals in Chequamegon Bay, WI

Bring your pet along with stays that welcome four-legged travelers.

Niche Suite at Ferry Landing Suites in Downtown La Pointe! - Chequamegon Bay, WI

Niche Suite at Ferry Landing Suites in Downtown La Pointe!

Apartment, Chequamegon Bay

Niche Suite at Ferry Landing Suites in Downtown La Pointe! is a apartment in Chequamegon Bay, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Niche Suite at Ferry Landing Suites in Downtown La Pointe!

Niche Suite at Ferry Landing Suites in Downtown La Pointe! is a apartment in Chequamegon Bay, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and tv.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,346.

From$335/night
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Superior View - 2 Bed/1 Bath Second-floor Apartment overlooking the Ferry Harbor! - Chequamegon Bay, WI

Superior View - 2 Bed/1 Bath Second-floor Apartment overlooking the Ferry Harbor!

Apartment, Chequamegon Bay

Superior View - 2 Bed/1 Bath Second-floor Apartment overlooking the Ferry Harbor! is a apartment in Chequamegon Bay, with pet-friendly space. This stay gives travelers a comfortable base…

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About Superior View - 2 Bed/1 Bath Second-floor Apartment overlooking the Ferry Harbor!

Superior View - 2 Bed/1 Bath Second-floor Apartment overlooking the Ferry Harbor! is a apartment in Chequamegon Bay, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, free wifi, pet friendly, and pets friendly.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,424.

From$346/night
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Calm-365 Guest Fav in Wisconsin - Chequamegon Bay, WI

Calm-365 Guest Fav in Wisconsin

Cabin, Chequamegon Bay

Calm-365 Guest Fav in Wisconsin is a cabin in Chequamegon Bay, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Calm-365 Guest Fav in Wisconsin

Calm-365 Guest Fav in Wisconsin is a cabin in Chequamegon Bay, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,475.

From$354/night
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Mary Ann`s - Located on Beautiful Russell Bay with Lake Access across the Street! - Chequamegon Bay, WI

Mary Ann`s - Located on Beautiful Russell Bay with Lake Access across the Street!

Holiday Home, Chequamegon Bay

Mary Ann`s - Located on Beautiful Russell Bay with Lake Access across the Street! is a holiday home in Chequamegon Bay, with easy beach access, parking, and kitchen access. This stay gives…

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About Mary Ann`s - Located on Beautiful Russell Bay with Lake Access across the Street!

Mary Ann`s - Located on Beautiful Russell Bay with Lake Access across the Street! is a holiday home in Chequamegon Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,970.

From$424/night
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Vacation rentals with parking in Chequamegon Bay, WI

Find vacation rentals that make arriving by car easier.

The Hermitage: An unplugged getaway in the woods on gorgeous Madeline Island. - Chequamegon Bay, WI

The Hermitage: An unplugged getaway in the woods on gorgeous Madeline Island.

Cabin, Chequamegon Bay

The Hermitage: An unplugged getaway in the woods on gorgeous Madeline Island. is a cabin in Chequamegon Bay, with parking and kitchen access. This stay gives travelers a comfortable base…

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About The Hermitage: An unplugged getaway in the woods on gorgeous Madeline Island.

The Hermitage: An unplugged getaway in the woods on gorgeous Madeline Island. is a cabin in Chequamegon Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,857.

From$265/night
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Outer Island Apartment @ The Copper Crown - Chequamegon Bay, WI

Outer Island Apartment @ The Copper Crown

Apartment, Chequamegon Bay

Outer Island Apartment @ The Copper Crown is a apartment in Chequamegon Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Outer Island Apartment @ The Copper Crown

Outer Island Apartment @ The Copper Crown is a apartment in Chequamegon Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,242.

From$320/night
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Parkside Condo 3 - Convenient In Town Condo - Chequamegon Bay, WI

Parkside Condo 3 - Convenient In Town Condo

Condo, Chequamegon Bay

Parkside Condo 3 - Convenient In Town Condo is a condo in Chequamegon Bay, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Parkside Condo 3 - Convenient In Town Condo

Parkside Condo 3 - Convenient In Town Condo is a condo in Chequamegon Bay, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $3,147.

From$450/night
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Parkside Condo 7 - Condo Conveniently Located Across from Joni`s Beach - Chequamegon Bay, WI

Parkside Condo 7 - Condo Conveniently Located Across from Joni`s Beach

Condo, Chequamegon Bay

Parkside Condo 7 - Condo Conveniently Located Across from Joni`s Beach is a condo in Chequamegon Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Parkside Condo 7 - Condo Conveniently Located Across from Joni`s Beach

Parkside Condo 7 - Condo Conveniently Located Across from Joni`s Beach is a condo in Chequamegon Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $3,181.

From$454/night
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Vacation rentals with a kitchen in Chequamegon Bay, WI

Compare stays with kitchen access for longer trips and easier meals.

Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the Street! - Chequamegon Bay, WI

Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the Street!

Holiday Home, Chequamegon Bay

Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the Street! is a holiday home in Chequamegon Bay, with parking and kitchen access. This stay gives travelers a…

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About Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the Street!

Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the Street! is a holiday home in Chequamegon Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,050.

From$293/night
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T West Lodging at Bell Street Downtown Madeline Island - Chequamegon Bay, WI

T West Lodging at Bell Street Downtown Madeline Island

Condo, Chequamegon Bay

T West Lodging at Bell Street Downtown Madeline Island is a condo in Chequamegon Bay, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About T West Lodging at Bell Street Downtown Madeline Island

T West Lodging at Bell Street Downtown Madeline Island is a condo in Chequamegon Bay, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, ac, air conditioning, and tv.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,413.

From$345/night
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Woodhaven - Charming Home nestled in the Woods, near Big Bay Town Park! - Chequamegon Bay, WI

Woodhaven - Charming Home nestled in the Woods, near Big Bay Town Park!

Cabin, Chequamegon Bay

Woodhaven - Charming Home nestled in the Woods, near Big Bay Town Park! is a cabin in Chequamegon Bay, with pet-friendly space, easy beach access, and parking. This stay gives travelers a…

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About Woodhaven - Charming Home nestled in the Woods, near Big Bay Town Park!

Woodhaven - Charming Home nestled in the Woods, near Big Bay Town Park! is a cabin in Chequamegon Bay, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,585.

From$369/night
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Bayfield Island View Lodging \"Sevona Suite\" on Lake Superior with Best Lake view - Chequamegon Bay, WI

Bayfield Island View Lodging \"Sevona Suite\" on Lake Superior with Best Lake view

Apartment, Chequamegon Bay

Bayfield Island View Lodging \"Sevona Suite\" on Lake Superior with Best Lake view is a apartment in Chequamegon Bay, with easy beach access, parking, and kitchen access. This stay gives…

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About Bayfield Island View Lodging \"Sevona Suite\" on Lake Superior with Best Lake view

Bayfield Island View Lodging \"Sevona Suite\" on Lake Superior with Best Lake view is a apartment in Chequamegon Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, beachfront, and beach front.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,650.

From$379/night
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