Sheboygan Area, Wisconsin Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Sheboygan Area, Wisconsin on RentalSaver.com!

Sheboygan Area Rentals

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VRBO
Lakeview Loft - Just opened up for July!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Looking for extended stays? We offer monthly rates. Inquire within, or check out StayWithNSD Bright and cozy 2-bedroom, ...
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VRBO
From $1598 per night (USD)
Expedia
Fairway Getaway-by Whistling Straits, Golf sim/Theater Room, ZenDen &Poker Room!
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Welcome to Fairway Getaway! This stunning property combines luxury, comfort, and convenience, making it the perfect choi ...
From $1598 per night (USD)
Expedia
From $283 per night (USD)
VRBO
NEW Three bedroom ranch style pet friendly home with a patio & theatre room!
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Located in a quiet neighborhood surrounded by wildlife. Concrete patio is perfect for bonfires and family bonding. Too c ...
From $283 per night (USD)
VRBO
From $149 per night (USD)
Expedia
Urban Lake Condo in Sheboygan's Historic Ellis District
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Your family will be within walking distance of almost everything when you stay at this centrally-located harborside gem ...
From $149 per night (USD)
Expedia
$Camp Skywood - New Listing!\n\n$
From $668 per night (USD)
VRBO
Camp Skywood - New Listing!\n\n
Bedrooms:
2
Bathrooms:
4
Sleeps:
2
Just minutes away from Downtown Elkhart Lake, this custom built cordwood home is truly a tucked away sanctuary. The 16 s ...
From $668 per night (USD)
VRBO
From $455 per night (USD)
Expedia
Waterfront Condo, Private Beach, Outdoor/Indoor Pools, & Walkable to Downtown
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Make summer memories at Elkhart Lake! Only 3 bedroom, 3 bath, condo located steps from the beach. Fully renovated in 2 ...
From $455 per night (USD)
Expedia
From $331 per night (USD)
VRBO
Lighthouse Lookout - 3BR / Steps to Lake Michigan & Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Lighthouse Lookout by Great Lakes Getaways! Discover the ultimate retreat at Sheboygan's Riverfront condo with stunning ...
From $331 per night (USD)
VRBO
From $445 per night (USD)
Expedia
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Welcome to The Hemisphere House, a unique dome retreat in a charming Wisconsin neighborhood. This architectural gem offe ...
From $445 per night (USD)
Expedia
From $510 per night (USD)
VRBO
State Park w/ Orchard Style Yard & Pavilion
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to our Orchard House Retreat, hosted by Sheboygan Vacation Rentals. Our home is situated directly across from t ...
From $510 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Cozy Corner Cottage- 2 blocks to Lake Michigan. Walk to Deland Park and Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Cozy Corner Cottage by Great Lakes Getaways! This charming Dutch Colonial house in Sheboygan’s historic Ellis District ...
From $306 per night (USD)
Expedia
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VRBO
Premier View and Patio Overlooking Elkhart Lake! Two minute walk to bars/dining!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy listening to bands from the private large patio while overlooking Elkhart Lake and the pool. Updated nice furnish ...
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VRBO
From $669 per night (USD)
Expedia
The Links! - Luxury Golf Retreat with Golf Simulator
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Get ready to relax in this 4-bedroom house in Sheboygan. This superb property features 2 king beds and 2 queen beds, per ...
From $669 per night (USD)
Expedia
From $835 per night (USD)
VRBO
Farm Fresh Eggs, Amazing Outdoor Space w/ Fire Pit
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
ESCAPE THE ORDINARY AT THIS ONE-OF-A-KIND, HISTORIC PROPERTY, Old Trees Farm, hosted by Sheboygan Vacation Rentals. You ...
From $835 per night (USD)
VRBO
From $243 per night (USD)
Expedia
Elkhart Lake, WI home close to lake, downtown, and Road America racetrack
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our cherished family home, nestled in the heart of a magical town that holds countless memories for us. We're ...
From $243 per night (USD)
Expedia
From $347 per night (USD)
VRBO
New! Breezy Beach - 75 Steps to Lake Michigan!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to Breezy Beach by Great Lakes Getaways! This villa is just 75 steps from Lake Michigan’s sandy shores, with fi ...
From $347 per night (USD)
VRBO
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Expedia
Shoreline Sanctuary - 4BR Villa w/ Lake Views, Beach Access & Sunsets
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Shoreline Sanctuary by Great Lakes Getaways! This stunning 4-bedroom, 3-bathroom beachfront villa on Lake Michigan offe ...
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Expedia
From $320 per night (USD)
VRBO
Wandering Waves - Beachfront condo right on Lake Michigan.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Wandering Waves by Great Lakes Getaways! Enjoy breathtaking Lake Michigan views from this updated 2-bedroom, 2-bathroom ...
From $320 per night (USD)
VRBO
From $327 per night (USD)
Expedia
Private Beach, Pools & Full-Kitchen
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Million-Dollar Views & Historic Charm – Private Condo along Elkhart Lake 🏊‍♂️ Indoor & outdoor pools 🔥 Hot tub 🌿 Exp ...
From $327 per night (USD)
Expedia
From $179 per night (USD)
VRBO
Sheboygan Sunrise Beach Stay
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
*** STEPS AWAY FROM LAKE MICHIGAN*** Experience the vibrant energy from our stylish apartment with great views. Enjoy e ...
From $179 per night (USD)
VRBO
From $402 per night (USD)
Expedia
NEW! Charming 3BR/2BA Lake House in the Woods of the desirable Black River area
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Your much-needed retreat begins at this large 3-bedroom house 300-feet from Lake Michigan. This wonderful property featu ...
From $402 per night (USD)
Expedia
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VRBO
2 Mi to Dtwn: Studio Suite in Sheboygan
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Pet Friendly w/ Fee | Walk to Diner & Brewery | Private Balcony Set sail for a getaway near the shore of Lake Michigan ...
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VRBO
From $1438 per night (USD)
VRBO
Beautiful Lake House with private access to Elkhart Lake
Bedrooms:
3
Bathrooms:
8
Sleeps:
18
Escape to our serene lake house, perfectly nestled on the shores of Elkhart Lake– a peaceful oasis ideal for families, c ...
From $1438 per night (USD)
VRBO
From $196 per night (USD)
VRBO
Apartment Centrally Located
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Only two laps from Road America, or 20 minutes from the beach, this secluded apartment complex is located on the peacefu ...
From $196 per night (USD)
VRBO
From $447 per night (USD)
Expedia
Home Near Road America & Elkhart Lake
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Close to Village Square | Pinball & Arcade Machine | Community Car Wash Bay Whether you’re here for lakefront fun or ex ...
From $447 per night (USD)
Expedia
From $349 per night (USD)
VRBO
New King Park Beach Lookout Deluxe! 3BR Right at Lake!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Welcome to King Park Beach Lookout Deluxe! Experience the perfect family getaway with panoramic views of Lake Michigan, ...
From $349 per night (USD)
VRBO
From $314 per night (USD)
Expedia
Riverwalk Retreat - Riverfront 3BR Condo w/ Jacuzzi & Lake Michigan Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Riverwalk Retreat by Great lakes Getaways! Discover the ultimate retreat in this top-floor Riverfront condo with stunni ...
From $314 per night (USD)
Expedia
From $331 per night (USD)
VRBO
Lakeside Condo - 2BR, Lake Michigan Views & Massage Chair
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Crystal Cove by Great Lakes Getaways! This lakeside condo boasts 2 bedrooms, 2 bathrooms, and a breathtaking view of La ...
From $331 per night (USD)
VRBO
From $328 per night (USD)
Expedia
The Cottage - Newly Renovated Beachfront Condo on Lake Michigan
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
The Cottage by Great Lakes Getaways! Escape to this newly renovated beachfront condo nestled along the serene shores of ...
From $328 per night (USD)
Expedia
From $247 per night (USD)
VRBO
Centrally located house minutes away from the lake, golfing, & Road America.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Get cozy on the big covered front porch by enjoying a cup of coffee or a local brew. Relax with a book or glass of wine ...
From $247 per night (USD)
VRBO
$LUX Uptown Escape - The Trester\n$
From $389 per night (USD)
Expedia
LUX Uptown Escape - The Trester\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our beautiful 2-bedroom historic home in Uptown Sheboygan! This charming and well-appointed residence offers ...
From $389 per night (USD)
Expedia
From $247 per night (USD)
VRBO
Riverfront Townhome with Breathtaking Water Views!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
*exterior fire table cannot be used after october 1. Welcome to Driftwood, our modern two-bedroom, 1.5-bath townhome, n ...
From $247 per night (USD)
VRBO
From $156 per night (USD)
Expedia
Cozy Cape Cod Home
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy cape cod home behind the Plymouth racetrack, loud during race season. Close to Road America (8 min; 5.8 miles), nea ...
From $156 per night (USD)
Expedia
From $331 per night (USD)
VRBO
Peaceful Retreat, Near Road America! Mid Century Modern Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Peaceful and private getaway in the woods, yet close to everything! Shops, restaurants, bars, parks, golf, fishing, sail ...
From $331 per night (USD)
VRBO
From $380 per night (USD)
VRBO
White House on the Mill Pond - kayak/walk downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
About this space A mix of vintage charm & contemporary/clean with leather couches, hardwood & tile floors. This is a 2 b ...
From $380 per night (USD)
VRBO
From $648 per night (USD)
VRBO
The Woods Estate - walk to Road America & near Kohler Golf ~ Modern Luxury
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Experience the beauty & comfort if this luxury contemporary home nestled in the woods on 5 acres walking distance to Ro ...
From $648 per night (USD)
VRBO
From $421 per night (USD)
Expedia
Perfect Paradise - Lakeview Condo w/ 7 Beds, Jacuzzi, and Balcony
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Perfect Paradise by Great Lakes Getaways! Unwind in this spacious 4-bedroom, 3-bath beachfront condo—perfect for famili ...
From $421 per night (USD)
Expedia
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VRBO
Cottage in the Woods walk to Lake Michigan!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Cottage in the black river area of Sheboygan County. Located on almost and acre of wooded property two blocks from publ ...
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VRBO
From $332 per night (USD)
Expedia
Newly Updated! Downtown & Shore
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...
From $332 per night (USD)
Expedia
From $633 per night (USD)
VRBO
4br Track View Townhome Next to Road America
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
With a view of Road America Racetrack, a short walk to Road America's Main Gate, a 5 minute drive into the historic Vill ...
From $633 per night (USD)
VRBO
From $782 per night (USD)
VRBO
Large lakefront Cabin w/ year-round activities & enough beds for everyone!
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
Relax with the whole family at this peaceful lakefront cabin! Wake up to stunning views and days filled with kayaking, h ...
From $782 per night (USD)
VRBO
From $264 per night (USD)
VRBO
Sheboygan Retreat in Black River
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Only an hour drive north of Milwaukee and south of Green Bay. Experience all Sheboygan County has to offer. Kohler gol ...
From $264 per night (USD)
VRBO
From $381 per night (USD)
VRBO
Family Fun on Crystal Lake Island - minutes to Road America, hiking, PGA Golf
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
**2025 and 2026 calendar is open. Please note that our peak season rentals are a week minimum and run Monday-Monday** T ...
From $381 per night (USD)
VRBO
From $2088 per night (USD)
VRBO
Beachfront property with panoramic view of Lake Michigan!
Bedrooms:
6
Bathrooms:
6
Sleeps:
20
Create memories at this beautiful Lake Michigan beachfront home. At the end of a private road, this year-round lake hous ...
From $2088 per night (USD)
VRBO
From $476 per night (USD)
VRBO
Heart of the Action, Village Square Upper Condo Sleeps 8
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Upper 4BR/2BA condo unit on the Village Park! Central location on Village Square across from historic train depot and re ...
From $476 per night (USD)
VRBO
From $306 per night (USD)
VRBO
Wonderful 3+ Bedroom Home Completely Renovated
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Beautiful home in Sheboygan WI. Entire home has been completely remodeled and updated. Three entire floors of space fo ...
From $306 per night (USD)
VRBO
From $783 per night (USD)
Expedia
Stunning custom built country home with the ultimate game room!
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
The search is over, you have found the PERFECT retreat at Oaks Haven! Experience the tranquility of nature surrounded by ...
From $783 per night (USD)
Expedia
From $199 per night (USD)
VRBO
cute and cozy-minutes from beaches,parks,trails,entertainment!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Cute comfortable open concept 2 bedroom apartment adjacent/ above The Dundee's Roadhouse super fun full service food and ...
From $199 per night (USD)
VRBO
From $355 per night (USD)
Expedia
Colorful Cottage w/ Hot Tub - Steps to Long Lake!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Prepare to experience lake life at this vacation rental in Campbellsport. Sitting across the street from Long Lake, this ...
From $355 per night (USD)
Expedia
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VRBO
RYDER CUP RENTAL : rustic lake front log cabin - 45min to Ryder Cup
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Log Cabin with loads of rustic charm situated on Forest Lake, Campbellsport, WI., a spring feed lake surrounded by the n ...
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VRBO
From $281 per night (USD)
Expedia
'McJugger’s Loft:' Walk to Lake, Park, Restaurants
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience small-town Wisconsin from this 3-bed, 2-bath vacation rental! 'McJugger's Loft' is ideal for a family trip, c ...
From $281 per night (USD)
Expedia
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VRBO
25 min. to Kohler Resort, Golf, Spa, Dining
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
This 5,500 square feet home sits directly on Lake Michigan. 6 Bedrooms and 4 full baths plus 2 1/2 baths. Located in Ced ...
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VRBO
From $503 per night (USD)
Expedia
The Lakehouse on Long Lake
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Our family always dreamt of owning a Lakehouse. When we had the opportunity to finally make that dream come true, we cra ...
From $503 per night (USD)
Expedia
From $427 per night (USD)
VRBO
Beautiful new year round Lake home on Long Lake in Kettle Moraine State forest
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Long Lake is a 432 Acre full recreational lake, known for water clarity, fishing, swimming, water skiing, boating , ice ...
From $427 per night (USD)
VRBO
From $233 per night (USD)
Expedia
Lillibridge Lake Home on Tittle Lake/Long Lake All Season Fun
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
The Lillibridge Lake House is just steps from the water on quaint Tittle Lake, nestled in the Kettle Moraine State Fores ...
From $233 per night (USD)
Expedia
From $367 per night (USD)
VRBO
Clara's Cottage, On Lake Michigan
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
The cottage is located approximately 45 minutes north of Milwaukee and ,10 minutes south of historic Sheboygan/Kohler ...
From $367 per night (USD)
VRBO
From $435 per night (USD)
Expedia
Lakefront Campbellsport Retreat w/ Dock & Yard!
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Discover your own slice of Wisconsin heaven at this 4-bedroom, 2.5-bathroom Campbellsport vacation rental! You'll be in ...
From $435 per night (USD)
Expedia
$Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan\n$
From $1619 per night (USD)
VRBO
Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan\n
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Escape to your own private Lakeside Retreat. 4 BR, 2.5 bath Cape Cod overlooking Lake Michigan & Black River giving you ...
From $1619 per night (USD)
VRBO
From $253 per night (USD)
Expedia
Near Hiking: Lakefront Getaway in Campbellsport!
Bedrooms:
1
Bathrooms:
4
Sleeps:
10
Nestled on 1.5 Acres | Pet Friendly w/ Fee | Families Welcome | BBQ Ready Escape from the hustle and bustle of daily li ...
From $253 per night (USD)
Expedia
From $543 per night (USD)
VRBO
Charming Retreat with Panoramic Views near Oostburg, Sheboygan, and Kohler
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Discover the epitome of lakeside living in this charming house nestled along Lake Michigan's serene shores, near Oostbur ...
From $543 per night (USD)
VRBO
From $512 per night (USD)
VRBO
On the Shores of Lake Michigan with Breathtaking Views & A Beach Out Your Door!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Private and Charming Beach Bungalow located on a secluded road! Who said this is a lake? This feels more like an ocean ...
From $512 per night (USD)
VRBO
$Welcome to the \Lake Cottage\ where lake Michigan waves are calling$
From $435 per night (USD)
VRBO
Welcome to the \"Lake Cottage\" where lake Michigan waves are calling
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Make memories of a lifetime at the “Lake Cottage” On a private gravel road right on the Lake 1.5 hours north of Chicago, ...
From $435 per night (USD)
VRBO
From $166 per night (USD)
Expedia
GGG Log Cabin Apartment on the Ice Age Trail
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
With 10-11’ ceilings and 1000 sf, this sunny apartment is the second floor of an 1860’s log cabin. Completely updated wi ...
From $166 per night (USD)
Expedia
From $8448 per night (USD)
VRBO
Serene Lakeview Retreat on Lake Michigan - Minutes to Whistling Straights
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Relax in this beautiful secluded home with breathtaking views of Lake Michigan. This spacious 4 bedroom home is showered ...
From $8448 per night (USD)
VRBO
$Lake/Trail Days- Campfire/Starry Nights-\nBeach Pier Hiking Stars Family Time$
From $218 per night (USD)
VRBO
Lake/Trail Days- Campfire/Starry Nights-\nBeach Pier Hiking Stars Family Time
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This A-frame cottage boasts 3 inviting bedrooms. The bedrooms will ensure a comfortable stay for all guests. The cozy a ...
From $218 per night (USD)
VRBO
From $202 per night (USD)
VRBO
LAKE HOUSE Relax'n in or on the water this is your place for memories to be made
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Kettle Moraine Long Lake Vacation Get Away. Comfort begins as you enter the door to your lake frontage studio style vaca ...
From $202 per night (USD)
VRBO
From $289 per night (USD)
Expedia
Cascade Lakefront Home: Boat Dock, Fire Pit!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Prepare for your ultimate lakeside retreat at this newly renovated Cascade lakefront property. Sitting right on Long Lak ...
From $289 per night (USD)
Expedia
From $283 per night (USD)
VRBO
Cottage in Campbellsport
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
The Retreat on Long Lake is the transformation of a cottage into a newly renovated and stylish experience. The house i ...
From $283 per night (USD)
VRBO
From $950 per night (USD)
VRBO
Newly renovated home on Lake Michigan - heated pool- Ozaukee County
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Wisco Lakehouse! Our lakefront home is perfect year-round for a fun family vacation, couple’s getaway, golf t ...
From $950 per night (USD)
VRBO
From $409 per night (USD)
VRBO
From Schwarz Supper Club to Road America, Schwarz Guest House is in Between.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
The Schwarz family has been taking care of friends and customers for over 55 years. Dinner, drinks, and a good time is ...
From $409 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Hidden Haven - Luxury Cottage w/ Hot Tub & Scenic Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hidden Haven by Great Lakes Getaways! Discover our new modern cottage on Lake Michigan’s coast, nestled on a spacious 3 ...
From $310 per night (USD)
Expedia

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Sheboygan Area Rentals

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Results: 370 Rentals