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Vacation Home Rentals in Sheboygan, Wisconsin

Vacation Home Rentals in Sheboygan, Wisconsin

Sheboygan Vacation Rentals - Anam Cara - On The Shores Of Lake Michigan
Sheboygan Vacation Rentals - Anam Cara - On the shores of Lake Michigan
House with 4 bedroom(s), 3 bathrooms(s), sleeps 12
0.5 miles to Sheboygan
Sheboygan, Wisconsin, 53081
Anam Cara ('Soul Friend' in Gaelic) is truly a unique space on the shores of Lake Michigan at Sheboygan, Wisconsin. With over 4000...

from 400 USD

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Sheboygan Vacation Rentals - Lake View Mansion B&B
Sheboygan Vacation Rentals - Lake View Mansion B&B
Bed and breakfast
0.5 miles to Sheboygan
Sheboygan, Wisconsin, 53081
Lake View Mansion Bed & Breakfast, Inc., is the only lodging facility in Sheboygan overlooking Lake Michigan. It offers panoramic views of the...
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Black River Log Cabin
Black River Log Cabin
House with 3 bedroom(s), sleeps 6
4.1 miles to Sheboygan
Sheboygan, 53081
Quaint 3 bedroom, 1.75 bath home on quiet, secluded, wooded double lot. Enjoy a quick walk to beautiful Lake Michigan for early morning sunrise...
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Blue Harbor Resort! Sleeps 8, Water Passes Included!
Condo with 2 bedroom(s), 2 bathrooms(s), sleeps 8
0.8 miles to Sheboygan
Sheboygan, 53081
Sorry, but NOT offering discounts for spring break, June, July, August or school holidays UNLESS there is availability four days prior to your...
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Golf And Leisure Retreat On The Shores Of Lake Michigan
Cottage with 4 bedroom(s), sleeps 12
5.9 miles to Sheboygan
Sheboygan, 53083
Relax and recharge at our unique historical leisure property on the shores of Lake Michigan. Come stay on our sixth generation farm and experience...
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Huge Luxury Wisconsin Rental Walk To The Beach!
House with 7 bedroom(s), 4 bathrooms(s), sleeps 14
1.1 miles to Sheboygan
Sheboygan, 53081
Sitting high on a hill with seasonal views of Lake Michigan, this 1889 home is ideally located for Lake Michigan, golf and sporting activities....
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Lake Michigan Shore - 160 Feet Of Private Beach - Sleeps 10
House with 4 bedroom(s), 3 bathrooms(s), sleeps 10
4.3 miles to Sheboygan
Sheboygan, 53081
Anam Cara, 'Soul Friend' in Gaelic, is truly a unique space. Sitting in the Black River Forest with its own 160 feet of Lake Michigan beach...

from 3,400 USD

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Scenic Lake Views In Sheboygan
Condo with 2 bedroom(s), sleeps 6
Sheboygan, 53081
Watch the sun come up over Lake Michigan across from the Sheboygan Marina and scenic lighthouse. Close to Whistling Straits (future site of the...
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The Beach House At Black River: Private Lake Michigan Beach
House with 3 bedroom(s), 1.5 bathrooms(s), sleeps 4
4.3 miles to Sheboygan
Sheboygan, 53081
Walk a few steps from the front door to the private beach for a stroll along Lake Michigan. Our lakefront home is about one mile north of...
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Vacation Home Rentals in the Sheboygan, Wisconsin Area

Sheboygan Falls Vacation Rentals - The Fringe, A Country Inn
Bed and breakfast
4.7 miles to Sheboygan
Sheboygan Falls, Wisconsin, 53085
The Fringe, A Country Inn, is an historic bed and breakfast inn located in Sheboygan Falls, Wisconsin. The Fringe is a perfect lodging...
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Plymouth Vacation Rentals - Gilbert Huson House
Bed and breakfast
12.7 miles to Sheboygan
Plymouth, Wisconsin, 53073
The Gilbert Huson House Bed and Breakfast, is Sheboygan County's oldest operating b&b inn. The elegant Victorian inn is perched on a tree-lined...
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Plymouth Vacation Rentals - Tauschek's B&B Log Home
Bed and breakfast
12.7 miles to Sheboygan
Plymouth, Wisconsin, 53073
Come home to comfort. Tauschek's Bed and BreakfastStaying at Tauschek's Log Home Bed and Breakfast promises to be more than just an experience. It...
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Port Washington Vacation Rentals - Port Washington Inn
Bed and breakfast
23.9 miles to Sheboygan
Port Washington, Wisconsin, 53074
Welcome to Port Washington, Wisconsin, an experience for the senses This Little City of Seven Hills is visually picturesque, tranquil in pace,...
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Manitowoc Vacation Rentals - Westport B&B
Bed and breakfast
23.9 miles to Sheboygan
Manitowoc, Wisconsin, 54220
When you cross the threshold of WestPort Bed & Breakfast you enter into the world of Midwestern Aristocracy. Amble through the 1879 Italianate...
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Oostburg Vacation Rentals - 2 Bdr Lake Michigan Vacation Cottage (Oostburg Wi)
Vacation rental with 2 bedroom(s), 1 bathrooms(s)
9 miles to Sheboygan
Oostburg, Wisconsin, 53070
Would you enjoy a secluded beach where you can enjoy the vast beauty of Lake Michigan? Would you like to take a hike in the woods over an ancient...

from 125 USD


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Blue Harbor Water Park Resort
Condo with 2 bedroom(s), 2 bathrooms(s), sleeps 8
0.8 miles to Sheboygan
Sheboygan, 53081
Be our guest. The place is all yours! Same resort amenities, same check-in procedures at resort. Full access to indoor water park! Just 75 steps...

from 119 USD

Daily


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Heart Of Kohler, Lovely Golf Retreat, ** 90 Day Minimum Rental
House with 3 bedroom(s), 2.5 bathrooms(s), sleeps 5
3.3 miles to Sheboygan
Kohler, 53044
This completely and meticulously renovated 1930’s home is in the village of Kohler, Wisconsin. Kohler is a Garden/Industry Community incorporated...

from 2,000 USD

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Private Getaway Surrounded By Nature - 5 Minutes From Kohler, Wi
House with 2 bedroom(s), 2.5 bathrooms(s), sleeps 6
6.3 miles to Sheboygan
Sheboygan Falls, 53085
Escape the rat race of life to this secluded bungalow hidden in mature evergreens and wildflowers. Enjoy the sun rise overlooking your private...

from 1,500 USD

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Stunning Lake Michigan Beach House
House with 3 bedroom(s), sleeps 14
6.8 miles to Sheboygan
Oostburg, 53070
Stunning Lake Michigan home. 270+ feet of beach access just steps from home. Has all the privacy one needs for a getaway with access to all...
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Luxury Lake Michigan Beach House Near Kohler Golf & Spa
House with 5 bedroom(s), 3.5 bathrooms(s), sleeps 18
7.5 miles to Sheboygan
Oostburg, 53070
Beautiful Luxury Lake Front Home just minutes away from the Kohler golf and spa and historic nautical Sheboygan. This private beach front home...

from 4,000 USD

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Luxury Lake Michigan Private Beachfront Home Near Kohler World Class Golf & Spa
Cottage with 4 bedroom(s), 3.5 bathrooms(s), sleeps 10
7.5 miles to Sheboygan
Oostburg, 53070
Stunning Lake Michigan Luxury Private Beachfront home with vistas to inspire & quality to admire. No expense has been spared in creating the...

from 2,500 USD

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Lake Michigan Beach House
House with 3 bedroom(s), 1.5 bathrooms(s), sleeps 7
8.3 miles to Sheboygan
Oostburg, 53070
Nestled between the pristine sandy shore of Lake Michigan and a forest of cedar and pine lies a modest beach house only a few steps from the lake....
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2.5 Hours From Chicago Private Lake Michigan Perfect Sand Beachfront Near Kohler
House with 5 bedroom(s), 3 bathrooms(s), sleeps 15
9 miles to Sheboygan
Oostburg, 53070
Near downhill skiing, Blue Harbor Indoor Water Park, and shopping. Experience the best that Wisconsin has to offer, without the long drive, at...

from 1,400 USD

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Aunt Dot's Cottage On The Shores Of Lake Michigan
Cottage with 3 bedroom(s), 2 bathrooms(s), sleeps 6
9 miles to Sheboygan
Oostburg, 53070
Aunt Dot's Cottage is the best of best worlds - so easy to get to about an hour north of Milwaukee just off Hwy 43, but a hidden treasure, "a...
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Beautiful Beachfront Cottage
House with 3 bedroom(s), 1.5 bathrooms(s), sleeps 6
9 miles to Sheboygan
Oostburg
Located on a private sandy beach, this cottage offers all the comforts of home. The cottage was renovated in 2006 to include new flooring, new...
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Lake Michigan Beach Front Home, 40 Minutes North Of Milwaukee
House with 3 bedroom(s), 3 bathrooms(s), sleeps 6
9 miles to Sheboygan
Oostburg, 53070
Beautiful Lake Michigan beach front home with multi-level decks overlooking 100' of private sandy beach. This charming four season house is water...

from 2,000 USD

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Newer 4 Seasons Lake Michigan Beach House
House with 3 bedroom(s), 2 bathrooms(s), sleeps 6
9 miles to Sheboygan
oostburg, 53070
Private sandy beach is just 15 steps from your front door. The sand is a special soft quality that rivals the best of the islands.This home was...
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Taking Summer Reservations 2013
Cottage with 3 bedroom(s), 1 bathrooms(s), sleeps 6
9 miles to Sheboygan
Oostburg, 53070
This is a special place for quiet, serene family, or couples vacation. Sit back, truly get away from your daily routines. There are no...
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Private And Cozy Vacation Cottage On Lake Michigan
Cottage with 2 bedroom(s), 1.5 bathrooms(s), sleeps 6
9.1 miles to Sheboygan
Oostburg, 53070
A small, rustic cottage on the shores of Lake Michigan. Built in the 1930s, it remains very 'up north' feeling, almost like a Hollywood version of...
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Lake Michigan Sand Beach & Wooded Privacy
Cottage with 2 bedroom(s), 1.5 bathrooms(s), sleeps 8
9.8 miles to Sheboygan
Oostburg, 53070
Located just east of Oostburg, Wisconsin beach and lake front home is a place to enjoy the seasons of Lake Michigan. You have your own 200 foot...
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Milwaukee Area Beach House On Lake Michigan
House with 2 bedroom(s), 1.5 bathrooms(s), sleeps 4
9.8 miles to Sheboygan
Oostburg, 53070
Cottage on Lake Michigan for rent, 140 miles north of Chicago 40 minutes north of Milwaukee. We love our house on Pine Beach but we can't be there...
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Milwaukee Area Beach House On Lake Michigan
House with 2 bedroom(s), 1.5 bathrooms(s), sleeps 4
9.8 miles to Sheboygan
Oostburg, 53070
Cottage on Lake Michigan for rent, 140 miles north of Chicago 40 minutes north of Milwaukee. We love our house on Pine Beach but we can't be there...
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Beauty On The Beach
Cottage with 2 bedroom(s), 1 bathrooms(s), sleeps 5
10.4 miles to Sheboygan
Oostburg, 53070
Our gem of a cottage is located directly on the Lake Michigan beach. It's near the village of Oostburg WI, about 12 miles south of Sheboygan, and...
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Large Waterfront 6 Br With Private Sand Beach And Tennis Court
House with 6 bedroom(s), 3.5 bathrooms(s), sleeps 16
10.5 miles to Sheboygan
Cedar Grove, 53013
TENNIS LOVERS! It has your own private tennis court! Experience the best that Wisconsin has to offer, without the long drive, at 'The Sand Dune'...

from 1,700 USD

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Secluded Luxury In The Country, Understated Elegance, All Amenities Imaginable
Farmhouse with 9 bedroom(s), 4 bathrooms(s), sleeps 18
11.5 miles to Sheboygan
Plymouth, 53073
Enjoy a cup of coffee out on the screened in Gazebo. Great evenings around the campfire. Large kitchen and 2 dining areas. Watch your favorite...

from 1,800 USD

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Lake Michigan Frontage Jewel
Cottage with 2 bedroom(s), 2 bathrooms(s), sleeps 5
12 miles to Sheboygan
Oostburg, 53070
If you would like to look at a spectacular sunrise in the morning and a sky that feels so close that you can touch every star in the evening, then...
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Windmill Beach -- The Best Of Both Worlds, Beach And Woods!
House with 2 bedroom(s), sleeps 6
12.8 miles to Sheboygan
Oostburg, 53070
House, 2 Bedrooms + Convertible Bed(s), 1 Bath (Sleeps 4-6) Our home on Windmill Beach is truly a sanctuary in that special Lake Michigan...
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Crystal Lake Lodge Northern Kettle Moraine Forest At Its Best
Chateau_/_country_house with 4 bedroom(s), sleeps 10
13.2 miles to Sheboygan
Plymouth, 53073
Winter wonderland get a way. Now offering a 2 night minimum. Have four couples stay for under $240.00 per couple for a two night stay or add an...
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"Saxon Sunrise" On Hika Bay Bluff, Beachfront - Lake Michigan
House with 3 bedroom(s), sleeps 10
13.9 miles to Sheboygan
Cleveland, 53015
Come and enjoy the beautiful sandy beaches of Lake Michigan at Saxon Sunrise on Hika Bay Bluff! Here you will enjoy a lakeshore paradise on your...
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'Saxon Sunrise' On Hika Bay Bluff, Beachfront - Lake Michigan
House with 3 bedroom(s), 1.5 bathrooms(s), sleeps 10
13.9 miles to Sheboygan
Cleveland, 53015
Come and enjoy the beautiful sandy beaches of Lake Michigan at Saxon Sunrise on Hika Bay Bluff! Here you will enjoy a lakeshore paradise on your...

from 1,295 USD

Weekly


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Road America Track Front Rental Home
House with 4 bedroom(s), sleeps 8
14 miles to Sheboygan
Plymouth, 53073
**Please view the custom website for more information, the link is listed below.** The Turn 3 Lodge is a classic split level, custom built home...
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Dream Vacation On Crystal Lake
House with 3 bedroom(s), sleeps 7
14.8 miles to Sheboygan
Plymouth, 53073
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Dream Vacation On Crystal Lake
Cottage with 3 bedroom(s), 2 bathrooms(s), sleeps 8
14.8 miles to Sheboygan
Plymouth, 53073
Beach front Amenities Garage : Two car garage Parking For RV/Boat/Trailer Linens Provided Clothes Dryer and washer Kitchen: Refrigerator...
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Shingle-Style Lake Michigan Home On Miles Of Sandy Beach
House with 5 bedroom(s), 4 bathrooms(s), sleeps 12
14.9 miles to Sheboygan
Cedar Grove, 53013
This architect designed 'green' home is on 41/2 acres with 150 feet on Lake Michigan. The house is on a private drive at lake level on a...

from 2,800 USD

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Charming Cottage On Horseshoe Lake Near Elkhart Lake/Kohler
Cabin with 2 bedroom(s), sleeps 10
15 miles to Sheboygan
Newton, 53063
We have a charming one bedroom cottage with sleeping loft(4 separate beds) and a detached guest house(sleeps two) located a few feet from the...
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Beautiful Crystal Lake Waterfront Cottage
Cottage with 4 bedroom(s), sleeps 12
15.1 miles to Sheboygan
Plymouth, 53073
Welcome to our Home on Beautiful Crystal Lake. Once you look 20 feet down into the crystal clear water of this spring fed lake you will truly...
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Crystal Lake/Grand View Lake Home
House with 3 bedroom(s), sleeps 10
15.1 miles to Sheboygan
Plymouth, 53073
Located just 100 yards from Sir Lancerlot golf course club house is a plus to take in a game of golf in the scenic rolling hills of the kettle...
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Lakeside Retreat Perfect For Racers & Golfers
House with 2 bedroom(s), 2 bathrooms(s), sleeps 8
15.2 miles to Sheboygan
Plymouth, 53073
This rental property is ideal for racers and spectators attending events at world famous Road America (two miles away), or for a great week of...
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2 Bed Apt. In Town Of Elkhart Lake, Great For Racers & Golfers
Apartment with 2 bedroom(s), sleeps 6
15.3 miles to Sheboygan
Elkhart Lake, 53020
2 Bedroom Apartment in the Village of Elkhart Lake! Great for Race Teams, Fans, and Golfers. Looking for a great place to stay in the Village of...
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Osthoff Resort Escape & Relax Water, Golf,Spa
Condo with 2 bedroom(s), 2 bathrooms(s), sleeps 4
15.3 miles to Sheboygan
Elkhart Lake, 53020
RELAX and ENJOY our custom decorated sports themed 2 BR/2 Bath Loft unit. Located in the AAA 4 diamond rated OSTHOFF RESORT. Conde Naste #1 Resort...
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