Unplugged Weekend - Vacation Rentals in Downtown

Sheboygan Chalet | Nature, Arcade, Sauna & Hot Tub From US $463
         

9.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Blue Harbor Resort and Conference Center From US $235
         

|
8.4 (448 Reviews)
Resort
  • Air Conditioner
  • Pool
  • Designated Smoking Area
Corner River Walk Condo with Spectacular Views From US $249
         

10.0 (45 Reviews)
Condo
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace

Luxury Places to Stay in Downtown

Over 251+ Luxury Places to Stay in or Near Downtown
Pelican Point - Private Retreat - just 4 miles to downtown Sheboygann From US $1,573
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Pelican Point - Private Retreat From US $1,250
         

|
New
House
  • Air Conditioner
  • Parking
  • View
Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX From US $1,163
         

Top-Rated Vacation Rentals with a Pool in Downtown

Over 17+ Top-Rated Vacation Rentals with a Pool in or Near Downtown
Home2 Suites By Hilton Sheboygan From US $122
         

|
9.6 (97 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Fairfield Inn & Suites by Marriott Sheboygan From US $121
         

|
9.4 (270 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Home2 Suites By Hilton Sheboygan From US $165
         

|
9.3 (46 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Sheboygan-Kohler by IHG From US $93
         

8.8 (379 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Grandstay Residential Suites Hotel - Sheboygan From US $124
         

8.6 (1019 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
AmericInn by Wyndham Sheboygan From US $81
         

8.6 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Comfort Inn & Suites Sheboygan I-43 From US $86
         

8.6 (152 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Sheboygan-Kohler/I-43 by IHG From US $188
         

|
8.5 (78 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Downtown

Over 61+ Pet-Friendly Vacation Rentals in or Near Downtown
Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan From US $391
         

|
10.0 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • Balcony/Terrace
La Quinta Inn by Wyndham Sheboygan From US $87
         

|
8.2 (1000 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced From US $388
         

*NEW* Sleeps 8 & Spacious! From US $186
         

10.0 (28 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Dog-Friendly Sheboygan Home - 1 Mi to Town! From US $125
         

10.0 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan From US $344
         

10.0 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Downtown on PetFriendly.io

Large Vacation Homes & Villas in Downtown

Over 58+ Large Vacation Homes & Villas in or Near Downtown
Spacious Sheboygan Home with Grill and Fire Pit! From US $563
         

|
9.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Accessibility
Beach front luxury spacious villa ! From US $325
         

10.0 (75 Reviews)
Villa
  • Air Conditioner
  • Parking
  • View

Wheelchair Accessible Vacation Homes in Downtown

Over 14+ Wheelchair Accessible Vacation Homes in or Near Downtown
Lake Orchard Farm Retreat From US $203
         

|
8.9 (43 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Watershed Hotel From US $136
         

|
9.6 (482 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home From US $230
         

10.0 (111 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Malibu of the Midwest Condo steps from the Lake From US $249
         

Modern South Pier Condo on Sheboygan River! From US $229
         

9.4 (33 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Waterfront Sheboygan Condo From US $237
         

Downtown waterfront condo. Full hook-up boat slip! Close to beach! Private deck! From US $150
         

10.0 (60 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • Designated Smoking Area

Downtown Vacation Rentals and Airbnb Places to Stay Under $200

Over 69+ Downtown Vacation Rentals and Airbnb Places to Stay Under $200
Harbor Winds Hotel From US $88
         

8.6 (939 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
REMODELED HOME ON LAKE MICHIGAN From US $176
         

9.8 (159 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Riverfront Sheboygan Townhome w/Grill! From US $167
         

10.0 (29 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
BEACHSIDE GETAWAY IN SHEBOYGAN From US $154
         

10.0 (27 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Eclectic Spacious 3 BR Home Near Lake MI w/Fire Pit From US $191
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pet-Friendly Sheboygan Home: 4 Mi to Lake Michigan From US $178
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Downtown

Over 114+ Instantly Bookable Vacation Homes in or Near Downtown
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown. From US $131
         

9.6 (11 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Family Home, 1 Block to Lake Michigan Beach! From US $375
         

10.0 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Beachside Condo w/Stunning Lake Views From US $216
         

10.0 (26 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Beachside Condo Downtown with Lake Michigan Views From US $204
         

LUXE Manor with Modern, Elegant Vibes From US $371
         

10.0 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
The Links! - Luxury Golf Retreat with Golf Simulator From US $493
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

About Downtown Vacation Rentals

With more than 5 Downtown vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Unpluggedweekend and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Downtown.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Unpluggedweekend Downtown, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Downtown. Places to stay near Downtown are 1369.38 ft² on average, with prices averaging $663 a night.

Unpluggedweekend makes it easy and safe to find and compare vacation rentals in Downtown with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Downtown

Type Count
Vacation Homes 3
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Downtown

Pro Tip: Unpluggedweekend makes it easy to compare the best listings on Unpluggedweekend homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Unpluggedweekend homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Downtown.

Weather in Downtown

View the weather forecast for Downtown before booking your Downtown Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Complexes around Downtown, WI


Downtown Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Downtown?

Currently, the total number of properties listed in 2026 is over 5 in the Downtown area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Downtown.