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

From $464 per night (USD)
VRBO
First Floor Pet Friendly Queen Suite with Single Pull-out
Bedrooms:
2
Bathrooms:
1
Sleeps:
3
WELCOME RACE FANS AND VACATIONERS!!!! The Victorian Inn is located along a picturesque freshwater lake and within walkin ...
From $464 per night (USD)
VRBO
From $379 per night (USD)
Expedia
Downtown Beachside Condo with Lake Michigan Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
You will see & hear the beauty of Lake Michigan during your stay at this main floor Waves of Happiness Condo hosted by S ...
From $379 per night (USD)
Expedia
$Beautiful Beachside Condo w\/ Stunning Lake Views$
From $432 per night (USD)
VRBO
Beautiful Beachside Condo w\/ Stunning Lake Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Blue water+White sand+Waves will surely make your stay in our second-floor Waves of Happiness Condo hosted by Sheboygan ...
From $432 per night (USD)
VRBO
From $180 per night (USD)
Expedia
Dog-Friendly Sheboygan Home - 1 Mi to Town!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience the best of Sheboygan with your loved one from this 1-bed, 1-bath vacation rental! This newly renovated home ...
From $180 per night (USD)
Expedia
From $778 per night (USD)
VRBO
Large Farmhouse near RA & golf. Breakfast Included with lots of room for all!
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
Discover Wirewalker Family Farm, a distinctive Bed and Breakfast nestled in the heart of Sheboygan County. Our recently ...
From $778 per night (USD)
VRBO
From $700 per night (USD)
Expedia
Luxury Villa on Lake Michigan!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Summary: Welcome to the ideal place on Lake Michigan for a family beach getaway, wind surfing, fishing, bachelorette wee ...
From $700 per night (USD)
Expedia
From $384 per night (USD)
VRBO
Relaxing home near Elkhart Lake
Bedrooms:
1
Bathrooms:
1
Sleeps:
7
Summary: Relax with the whole family at this peaceful place to stay. Minutes from both downtown Elkhart lake and Road Am ...
From $384 per night (USD)
VRBO
From $358 per night (USD)
Expedia
Family friendly farmhouse near Cascade with AC, WiFi. Enjoy a peaceful retreat!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Escape to the tranquility of country living at The Farmhouse on Mink Creek. Nestled on an acre surrounded by picturesque ...
From $358 per night (USD)
Expedia
From $715 per night (USD)
VRBO
Road America and Golf Retreat
Bedrooms:
2
Bathrooms:
4
Sleeps:
18
Escape to tranquility at our charming rental, nestled in serene woods, just down the road from Road America and premier ...
From $715 per night (USD)
VRBO
From $727 per night (USD)
Expedia
NFL Draft, Road America and near beautiful downtown Elkhart Lake
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Experience Elkhart Lake like a local in this 4-bedroom house. With 3 queen beds, 3 twin beds, and 1 king bed, this lovel ...
From $727 per night (USD)
Expedia
From $1342 per night (USD)
VRBO
Sleeps 8! Adjoined rooms!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
WELCOME RACE FANS AND VACATIONERS!! The Victorian Inn is located along a picturesque freshwater lake and within walking ...
From $1342 per night (USD)
VRBO
From $665 per night (USD)
Expedia
Luxury Lake Front Villa: Sleeps 12!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Experience the ultimate in luxury at this exquisite 4 bedroom lakefront vacation rental on Lake Michigan, just minutes f ...
From $665 per night (USD)
Expedia
From $271 per night (USD)
VRBO
On the Water in Sheboygan River Overlook
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The views from inside make it feel as if the home is overhanging the beautiful Sheboygan River. Go kayaking, enjoy the ...
From $271 per night (USD)
VRBO
$\nPlymouth Gem: Spacious Home with Bar, Game Room & Yard Near Road America$
From $575 per night (USD)
Expedia
\nPlymouth Gem: Spacious Home with Bar, Game Room & Yard Near Road America
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Your cozy getaway awaits in Plymouth at this marvelous house. With 3 queen beds and one full size bed spread across 4 be ...
From $575 per night (USD)
Expedia
From $176 per night (USD)
VRBO
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Welcome to the Beachy Bungalow! Come in and unwind at our beachy 3 bedroom upper unit near Lake Michigan, Whistling Str ...
From $176 per night (USD)
VRBO
From $186 per night (USD)
Expedia
Charming 2-bedroom condo with WiFi, AC in quaint Sheboygan
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This fantastic condo in Sheboygan offers two bedrooms with queen beds, perfect for a relaxing getaway. With amenities li ...
From $186 per night (USD)
Expedia
$Baronwood Oasis-Indoor Pool\/Spa-Arcades-16beds-LUX$
From $1458 per night (USD)
VRBO
Baronwood Oasis-Indoor Pool\/Spa-Arcades-16beds-LUX
Bedrooms:
7
Bathrooms:
7
Sleeps:
20
🏡 Welcome to Baronwood Oasis – The Ultimate Family Escape - Sleeps 20 This is your moment to be the hero of your famil ...
From $1458 per night (USD)
VRBO
From $882 per night (USD)
Expedia
Blue Barn on the Green with Farm House near the shores of Lake Michigan
Bedrooms:
5
Bathrooms:
5
Sleeps:
18
Welcome to this charming farmhouse and event barn in Oostburg. Imagine your perfect countryside escape. Nestled on five ...
From $882 per night (USD)
Expedia
From $163 per night (USD)
VRBO
Lake Breeze on 11th
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Sheboygan has lots to offer & our place is perfect for your homebase. The lakefront, Sunrise, End, & Vollrath park are j ...
From $163 per night (USD)
VRBO
From $1102 per night (USD)
Expedia
Boho Farmhouse-Huge Backyard-Golfers Paradise-Charter Hill Retreat
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Experience the charm of our cozy home away from home! Comfortably situated halfway between Milwaukee & Green Bay, it is ...
From $1102 per night (USD)
Expedia
From $211 per night (USD)
VRBO
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Welcome to the Coastal Comfort! Comfort: noun - a state of physical ease and freedom from pain or constraint Come in a ...
From $211 per night (USD)
VRBO
From $211 per night (USD)
Expedia
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Welcome to the Getaway! Getaway: noun - an act or instance of getting away; a place suitable for a vacation You will u ...
From $211 per night (USD)
Expedia
$Black River Retreat\nEclectic-Unique-Intriguing$
From $229 per night (USD)
VRBO
Black River Retreat\nEclectic-Unique-Intriguing
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Wow. An amazing home in an amazing location. Minutes from downtown Sheboygan, beaches at Kohler Andre & Lakeview parks, ...
From $229 per night (USD)
VRBO
From $411 per night (USD)
Expedia
2 Mi to Road America: Pet-Friendly Duplex!
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Walk to Elkhart Lake | Next to Quit Qui Oc Golf Course Indulge in a mix of tranquility and fun at this 4-bedroom, 2-bat ...
From $411 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Riverside Retreat with lots of local golf courses, beaches, and restaurants!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Cozy Riverside Retreat in Historic Sheboygan Falls Welcome to your perfect getaway in the heart of historic Sheboygan F ...
From $231 per night (USD)
VRBO
From $456 per night (USD)
Expedia
Sunset Vista 2br in Sheboygan
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This cozy vacation rental is a perfect place to relax and enjoy a getaway! From its warm and inviting fireplace, with co ...
From $456 per night (USD)
Expedia
From $897 per night (USD)
VRBO
1 min from Road America and the Village of Elkhart Lake
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
This amazing vacation lodge is the perfect getaway spot for families and friends. Nestled on a private lot, surround by ...
From $897 per night (USD)
VRBO
$\n\nLuxury Downtown Sheboygan 4 Bdr 3 min walk to beach - Lakeside Legacy$
From $969 per night (USD)
Expedia
\n\nLuxury Downtown Sheboygan 4 Bdr 3 min walk to beach - Lakeside Legacy
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Grand colonial meets coastal luxe in this 2800 square ft, 4 bedroom home along the magnificent Lake Michigan coast. Stun ...
From $969 per night (USD)
Expedia
From $500 per night (USD)
VRBO
NEW! Indigo Waters- Steps to the sand! Sleeps 7! Book today!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Indigo Waters by Great Lakes Getaways! Step into this vibrant, updated condo where bold colors and unique touches make ...
From $500 per night (USD)
VRBO
From $531 per night (USD)
VRBO
Charming 4-bedroom house with WiFi and AC in lovely Sheboygan
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Unwind in this fabulous 1970's home with modern upgrades. This spacious 3700 SF retreat features 4 bedrooms (3 queen, ...
From $531 per night (USD)
VRBO
From $260 per night (USD)
VRBO
Steps from Lake Michigan: North Point Place
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Conveniently located for adventure and relaxation along the lakeshore and beyond, this historic home is steps away from ...
From $260 per night (USD)
VRBO
From $145 per night (USD)
VRBO
Cozy and private 3 bedroom unit located a few blocks from downtown Sheboygan.
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Located just a couple blocks from downtown Sheboygan! Visit the shops and unique restaurants just a short walk away, or ...
From $145 per night (USD)
VRBO
$Eclectic Spacious 3 BR Home Near Lake MI w\/ Fire Pit$
From $219 per night (USD)
VRBO
Eclectic Spacious 3 BR Home Near Lake MI w\/ Fire Pit
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to the Relax ‘n Retreat! Retreat: noun - a quiet or secluded place in which one can rest and relax Unwind at o ...
From $219 per night (USD)
VRBO
From $554 per night (USD)
VRBO
Close to Downtown Elkhart Lake!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Located 7 blocks from Beautiful Clear Elkhart Lake. Summertime is a Great Time in Elkhart Lake with the Lake for swimmin ...
From $554 per night (USD)
VRBO
From $230 per night (USD)
VRBO
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Place is all for you! No share place. Forget your worries in this spacious and serene Guest House ( sleeps 4 people) q ...
From $230 per night (USD)
VRBO
From $319 per night (USD)
Expedia
Logan Ave Holiday House - Upper
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Unique attractions and endless days by Lake Michigan await at this ideally located vacation rental! Hosting 2 bedrooms, ...
From $319 per night (USD)
Expedia
From $701 per night (USD)
VRBO
Beautiful home - Great for Road America, golf outings, NFL Draft, or just R&R!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Beautiful home in a quiet neighborhood. Less than a minute from Road America, 10 minutes to Elkhart Lake. Enjoy the to ...
From $701 per night (USD)
VRBO
From $460 per night (USD)
VRBO
Retreat to Crystal Lake
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Beautiful Home on Crystal Lake. 120 feet of lake frontage. Large front yard and patio allows you to enjoy the beautifu ...
From $460 per night (USD)
VRBO
From $987 per night (USD)
VRBO
Modern Lakeside House with Treehouse
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
Welcome to Curtiss Castle! Ideal for large families, remote workers, lake lovers, and golf enthusiasts! This peaceful, w ...
From $987 per night (USD)
VRBO
$Lake House w\/ 6-BR's near Kohler-Andrae\/Sheboygan$
From $1463 per night (USD)
Expedia
Lake House w\/ 6-BR's near Kohler-Andrae\/Sheboygan
Bedrooms:
4
Bathrooms:
9
Sleeps:
15
Welcome to the House at Wilson Shore hosted by Sheboygan Vacation Rentals. Escape to the serene beauty of this stunning ...
From $1463 per night (USD)
Expedia
From $237 per night (USD)
VRBO
Elegant Condo in Historic Sheboygan Falls, Licensed and inspected by Sheb County
Bedrooms:
2
Bathrooms:
2
Sleeps:
14
Beautiful Upper Condo in Historic Sheboygan Falls. Licensed and professionally inspected by Sheboygan County, next to th ...
From $237 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Beach House on the shores of Lake Michigan Near downtown Sheboygan
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Amazing location on the shores of Lake Michigan. One of only a few homes in the city of Sheboygan that are right on the ...
From $402 per night (USD)
Expedia
Click For Pricing
VRBO
Cozy Townhouse by Road America
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
• 4 car garage-heated+cooled garage • Gas fireplace • Gas grill on patio • Keyless entry • Washer+dryer–soap/dryer sheet ...
Click For Pricing
VRBO
From $562 per night (USD)
VRBO
Racer’s Getaway - Rural, Upscale, Unique Home 8 minutes from Road America
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Our home is located on a very private 50 acre hobby farm in rural Elkhart Lake approximately 6 miles from Road America a ...
From $562 per night (USD)
VRBO
From $1274 per night (USD)
VRBO
NEW!! Luxury Rental - Parker House. Private Beach Access & Walkable to Downtown
Bedrooms:
5
Bathrooms:
5
Sleeps:
14
Welcome to Parker House, a private vacation rental situated in Elkhart Lake, Wisconsin! Parker House is located off the ...
From $1274 per night (USD)
VRBO
From $136 per night (USD)
VRBO
COMFY, COZY, and CONVENIENT!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Whether you are here for golf, fishing, a Green Bay Packer game, Road America, or simply a vacation, this convenient She ...
From $136 per night (USD)
VRBO
From $421 per night (USD)
VRBO
Private home on twenty wooded acres.
Bedrooms:
2
Bathrooms:
0
Sleeps:
0
Located in the Northern Kettle Moraine Forest, this property is an hour north of Milwaukee and one hour and twenty minut ...
From $421 per night (USD)
VRBO
$Downtown Sheboygan Apartment w\/ Private Deck!$
From $274 per night (USD)
Expedia
Downtown Sheboygan Apartment w\/ Private Deck!
Bedrooms:
1
Bathrooms:
5
Sleeps:
8
Nestled in the heart of downtown, this 4-bedroom, 1-bathroom Sheboygan vacation rental is a walkable utopia for your nex ...
From $274 per night (USD)
Expedia
From $551 per night (USD)
VRBO
The Kohler House
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
The Kohler House is located in the quaint village of Kohler. Our family grew up in this neighborhood and created a spac ...
From $551 per night (USD)
VRBO
From $472 per night (USD)
Expedia
Wander Back Inn to Elkhart Lake
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This gorgeous, new home is the perfect choice for your trip to Elkhart. Mere minutes away from famous local attractions ...
From $472 per night (USD)
Expedia
From $716 per night (USD)
VRBO
Road America Adjacent Lake House with indoor pool
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Road America adjacent four bedroom house on Little Elkhart Lake with indoor pool and spacious deck overlooking Little El ...
From $716 per night (USD)
VRBO
From $716 per night (USD)
Expedia
Crystal Lake Cottage: Kayaks & Fire Pit!
Bedrooms:
2
Bathrooms:
8
Sleeps:
14
Lake Access On-Site | 3 Paddleboards | Pet Friendly w/ Fee | Outdoor Living Space A relaxing lakefront getaway awaits y ...
From $716 per night (USD)
Expedia
From $494 per night (USD)
VRBO
Wander Back Inn to Sheboygan
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
*Bring the whole family to this great place with lots of room for fun. Plenty of space inside and out! Foosball and ping ...
From $494 per night (USD)
VRBO
From $323 per night (USD)
Expedia
The RandomCabin “On Random Lake”
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Suprising. Waterfront. Cozy. Unique. Rustic. Modern. These all describe the Random Cabin. In the Small inviting village ...
From $323 per night (USD)
Expedia
From $264 per night (USD)
VRBO
Elkhart Lake Flat - 3 min. to Road America
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This rental is a fully furnished with two bedrooms, two portable single cots, one bath, full stocked kitchen, dining roo ...
From $264 per night (USD)
VRBO
From $688 per night (USD)
Expedia
SCCA Nation Championship runoffs rental! Elkhart Lake!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Stay in the heart of Elkhart Lake in this unique hotel room style condo. This listing is one oversized hotel room with i ...
From $688 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Private, Peaceful Retreat near Road America
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
If you like racing, hiking, biking, golf, antiquing or fishing our quaint, quiet apartment is for you! Road America race ...
From $193 per night (USD)
VRBO
Click For Pricing
Expedia
Historic 1920s home with high speed WIFI and Air Conditioning
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Enjoy the comfort and charm of this historic 1920s custom built home. The beauty of this home resonates with its custom ...
Click For Pricing
Expedia
$Apt w\/ Shared Gas Grill, 2 Blocks to Dtwn!$
Click For Pricing
VRBO
Apt w\/ Shared Gas Grill, 2 Blocks to Dtwn!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Escape to Lake Michigan when you choose this centrally located Sheboygan vacation rental! Bring your fishing rods to spe ...
Click For Pricing
VRBO
From $809 per night (USD)
Expedia
'Beautiful Day Getaway' - Lake Michigan Views
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Set your sights on the coastal community of Sheboygan, where you can find 2 miles of sandy beaches, epic sailing, and a ...
From $809 per night (USD)
Expedia
$Lakefront Plymouth Cottage w\/ Private Hot Tub$
From $415 per night (USD)
VRBO
Lakefront Plymouth Cottage w\/ Private Hot Tub
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Get ready to make a splash when you book this 2-bedroom, 2-bath Plymouth vacation rental! With 3 flat-screen TVs, a full ...
From $415 per night (USD)
VRBO
$Spacious Property, Hot Tub, Sleeps up to 9, EV Charger\n$
From $489 per night (USD)
Expedia
Spacious Property, Hot Tub, Sleeps up to 9, EV Charger\n
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Spring into making memories at THE PINES located in the beautiful southern Kettle Moraine Forest area. The property is ...
From $489 per night (USD)
Expedia
From $482 per night (USD)
VRBO
5 Bedroom Modern House
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
5 bedroom modern home. Full kitchen includes dishwasher, microwave, stove, fridge, keurig, everyday utensils and pans. P ...
From $482 per night (USD)
VRBO
$GUEST HOUSE SHORT WALK TO LAKE MICHIGAN\/Close to Downtown & S Pier\n4bdrm 2 bath$
From $600 per night (USD)
Expedia
GUEST HOUSE SHORT WALK TO LAKE MICHIGAN\/Close to Downtown & S Pier\n4bdrm 2 bath
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Amazing location just 3 blocks of Lake Michigan. a short walk to the public south beach, 2 min driving to the beach. 4 ...
From $600 per night (USD)
Expedia
From $1354 per night (USD)
VRBO
Experience Gracious Living & Destination Kohler
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome! NEW spacious 4000ft² lodging centrally located: 5 World-Class golf courses, Road America, Elegant Wineries/Spas ...
From $1354 per night (USD)
VRBO
From $145 per night (USD)
Expedia
Country Cheese Factory - King Bed!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
See our other home and many reviews! https://airbnb.com/h/plymouth-guest-house Entire House! 4 minutes from Road Americ ...
From $145 per night (USD)
Expedia
From $216 per night (USD)
VRBO
Wyatt's Country Home - King Bed!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Soak up the modern vintage charm of our fully remodeled and updated home! Thank you for choosing our sparkling clean spa ...
From $216 per night (USD)
VRBO
From $450 per night (USD)
Expedia
Beautiful, newly built 3rd floor Townhouse in historic Elkhart Lake, WI.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautifully appointed, third floor Townhouse at the Trackside Townhouses across the road from famous Road America. Short ...
From $450 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Country Guest House
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
See our other listing! https://airbnb.com/h/cheese-factory-bnb Entire house! Cozy Warm! This beautiful and unique guest ...
From $268 per night (USD)
VRBO
$Spacious Sheboygan Home w\/ Grill & Fire Pit!$
From $554 per night (USD)
Expedia
Spacious Sheboygan Home w\/ Grill & Fire Pit!
Bedrooms:
3
Bathrooms:
7
Sleeps:
10
Escape the mundane and discover Lake Michigan bliss at this 5-bedroom, 3-bathroom Sheboygan vacation rental! Start your ...
From $554 per night (USD)
Expedia
From $395 per night (USD)
VRBO
*NEW* Sleeps 8 & Spacious!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...
From $395 per night (USD)
VRBO
Click For Pricing
VRBO
Trendy 2-bedroom townhouse next to Road America
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
• 4 car garage-heated AND cooled garage • Gas fireplace • Gas grill on patio • Seating on second floor deck • Keyless en ...
Click For Pricing
VRBO
From $1098 per night (USD)
VRBO
NEW!! Waterfront Condo at Victorian Village Lakeside Suites!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
WELCOME RACE FANS AND VACATIONERS!!!! The Lakeside Suitesare located along a picturesque freshwater lake and within walk ...
From $1098 per night (USD)
VRBO
From $1334 per night (USD)
Expedia
1-Mile to Road America, 2-Miles to Elkhart Lake
Bedrooms:
3
Bathrooms:
7
Sleeps:
18
Experience rustic charm in our "Big Montana" Log Cabin located at Elkhart Lodge. The Big Montana cabin, hosted by Shebo ...
From $1334 per night (USD)
Expedia
Click For Pricing
VRBO
Top Floor Condo With Lake Michigan Views Throughout!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Relax in this luxurious new construction condo! Enjoy top floor Lake Michigan Views from every room! Balcony with lots o ...
Click For Pricing
VRBO
From $335 per night (USD)
Expedia
Chic Plymouth Townhome < 1 Mi to Road America
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Prepare for an unforgettable retreat at this 2-bedroom, 2-bathroom Plymouth vacation rental next to Road America! Nestle ...
From $335 per night (USD)
Expedia
Click For Pricing
VRBO
Northside Charmer!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Charming Northside Sheboygan home just 5 miles from Whistling Straits, a ten minute walk to Lake Michigan and 15 minute ...
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VRBO
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Expedia
5mi from the Ryder Cup @ Whistling Straits, natural beauty and serenity awaits!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Sleeping 8, this ranch home located just 6 miles as the crow flies from Whistling Straits golf course, offers a relaxing ...
Click For Pricing
Expedia
$Riverfront Sheboygan Townhome w\/ Grill!$
From $329 per night (USD)
VRBO
Riverfront Sheboygan Townhome w\/ Grill!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Find rest and relaxation where the Sheboygan River flows into Lake Michigan at this 2-bedroom, 1.5-bathroom townhome. Th ...
From $329 per night (USD)
VRBO
From $313 per night (USD)
Expedia
*NEW* Beautiful & Convenient!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...
From $313 per night (USD)
Expedia
$Sheboygan Getaway w\/ Deck + On-Site Lake Access!$
From $285 per night (USD)
VRBO
Sheboygan Getaway w\/ Deck + On-Site Lake Access!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Plan for plenty of outdoor fun on your next Lake Michigan getaway when you stay at this Sheboygan vacation rental! With ...
From $285 per night (USD)
VRBO
Click For Pricing
Expedia
Remodeled Cape Cod within steps of Lake Michigan
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Our charming Cape Cod home is waiting for you! With 3 bedrooms, and 1.5 baths, we’re sure our home will meet the needs o ...
Click For Pricing
Expedia
From $1755 per night (USD)
VRBO
Cute Quiet Neighborhood Hideway
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Step back in time and relax in this 1930’s bungalow. Situated on the south side of the City of Sheboygan, able to feel t ...
From $1755 per night (USD)
VRBO
From $505 per night (USD)
VRBO
Luxurious artistic 2 bed - 2 bath Condo; feel like living by the Coast!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This is a very well-taken care of condo in the most touristic part of Sheboygan. Be close to two beaches, a pier walk, a ...
From $505 per night (USD)
VRBO
From $146 per night (USD)
VRBO
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 $146 per night (USD)
VRBO
From $373 per night (USD)
Expedia
NEW Three bedroom ranch style pet friendly home with a patio & theatre room!
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Located in a quiet neighborhood surrounded by wildlife. Concrete patio is perfect for bonfires and family bonding. Too c ...
From $373 per night (USD)
Expedia
$Lovely Lake Lookout – 67.4 miles \/ 1 hr to the NFL Draft at Lambeau Field!$
From $424 per night (USD)
VRBO
Lovely Lake Lookout – 67.4 miles \/ 1 hr to the NFL Draft at Lambeau Field!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Lovely Lake Lookout by Great Lakes Getaways! Unwind at this cozy 2BR/2BA condo just moments from Lake Michigan. Enjoy e ...
From $424 per night (USD)
VRBO
From $631 per night (USD)
Expedia
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled in the heart of Sheboygan, our location is a true gem! We are just steps away from the shores of Lake Michigan a ...
From $631 per night (USD)
Expedia
From $708 per night (USD)
VRBO
Stunning Lakefront Cottage
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Our Lakefront Cottage is a relaxing escape for nature enthusiasts and those seeking a peaceful retreat. Our newly remode ...
From $708 per night (USD)
VRBO
From $341 per night (USD)
Expedia
Modern South Pier Condo on Sheboygan River!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Stay in luxury at this 2-bedroom, 2-bathroom vacation rental in Sheboygan, WI. Enjoy the convenience of a fully equipped ...
From $341 per night (USD)
Expedia
From $209 per night (USD)
VRBO
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
About this space: Renovated 1930's home located in the historic downtown district within walking distance of breathtakin ...
From $209 per night (USD)
VRBO
$tranquil cabin on 5 private acres w\/ hot tub and sauna$
From $352 per night (USD)
Expedia
tranquil cabin on 5 private acres w\/ hot tub and sauna
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Need a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming ...
From $352 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Lovely Elkhart Lake Apartment - Walk to Town!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Move into an airy Wisconsin getaway for the weekend, where you can stroll to beautiful Elkhart Lake or fire up grills fo ...
From $203 per night (USD)
VRBO
From $193 per night (USD)
Expedia
Historic Home in Quiet Central Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
You will be close to everything when you stay at this 1930s home. Walk three blocks west to Sheboygan's historic downtow ...
From $193 per night (USD)
Expedia
$Spacious Blue Harbor 2 bedr courtyard view condo w\/ Breaker Bay Waterpark access$
Click For Pricing
VRBO
Spacious Blue Harbor 2 bedr courtyard view condo w\/ Breaker Bay Waterpark access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Detach yourself from the main crowd and check yourself into the 1242 square feet of spacious privacy of your own lakesid ...
Click For Pricing
VRBO
$Fairway Getaway-by Whistling Straits, Golf sim\/Theater Room, ZenDen &Poker Room!$
From $1598 per night (USD)
Expedia
Fairway Getaway-by Whistling Straits, Golf sim\/Theater Room, ZenDen &Poker Room!
Bedrooms:
4
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
$Lighthouse Lookout – 67.3 miles \/ 1 hr to the NFL Draft at Lambeau Field!$
From $309 per night (USD)
VRBO
Lighthouse Lookout – 67.3 miles \/ 1 hr to the NFL Draft at Lambeau Field!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Lighthouse Lookout by Great Lakes Getaways! Discover the ultimate retreat at Sheboygan's Riverfront condo with stunning ...
From $309 per night (USD)
VRBO
$Camp Skywood - New Listing!\n\n$
From $1202 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 $1202 per night (USD)
VRBO
$Waterfront Condo, Private Beach, Outdoor\/Indoor Pools, & Walkable to Downtown$
From $504 per night (USD)
VRBO
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 $504 per night (USD)
VRBO
$State Park w\/ Orchard Style Yard & Pavilion$
From $490 per night (USD)
Expedia
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 $490 per night (USD)
Expedia

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