Charters By Owner - Vacation Rentals in Southside

The Harwood House From US $160
         

10.0 (82 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Trickling Waters Retreat From US $96
         

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9.5 (116 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Trickling Waters Retreat From US $100
         

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9.8 (285 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Ohio Street Retreat-hot tub, massage chair, pool From US $193
         

10.0 (71 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Copper Roof Cottage From US $212
         

10.0 (54 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Becwar House . . . at the Mississippi River From US $273
         

10.0 (35 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace

Luxury Places to Stay in Southside

Over 57+ Luxury Places to Stay in or Near Southside
Water Street Lodge! Waterfront 4 Bedroom, 4 Bath, Sleeps 12! From US $568
         

9.4 (35 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Custom Waterfront Lodge, 4 bed, 4 Bath, Sleeps 12! From US $562
         

Historic Victorian Apartment From US $254
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
American House 1854- Steamboat Landing, 4 Bedrooms, 1.5 Bath, Full Kitchen From US $245
         

The Rivertown Getaway From US $227
         

10.0 (56 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Top-Rated Vacation Rentals with a Pool in Southside

Over 9+ Top-Rated Vacation Rentals with a Pool in or Near Southside
River District Hotel From US $143
         

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9.3 (78 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Windsor Place Inn From US $60
         

8.4 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Country Inn & Suites by Radisson, Prairie du Chien From US $85
         

Microtel Inn & Suites by Wyndham Prairie du Chien From US $81
         

Quality Inn & Suites Prairie Du Chien From US $66
         

8.2 (435 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Country Inn & Suites by Radisson, Prairie du Chien From US $92
         

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8.1 (425 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
AmericInn by Wyndham Prairie du Chien From US $68
         

8.0 (587 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Quality Inn & Suites Prairie Du Chien From US $80
         

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7.9 (300 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Southside

Over 11+ Pet-Friendly Vacation Rentals in or Near Southside
Historic Sadie's Log Cabin From US $174
         

10.0 (5 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Bluffside Chalet Suite From US $198
         

9.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Newly updated historical home From US $153
         

9.8 (59 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Windsor Place Inn From US $84
         

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8.2 (407 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Rustic 3Bed 2Bath Home near Downtown PDC From US $153
         

Comfort Inn & Suites Marquette - Prairie du Chien From US $123
         

8.1 (95 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Copper Roof Cottage From US $257
         

10.0 (49 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
House on the Hill within walking distance of shopping and marina! From US $129
         

10.0 (33 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Southside

Over 2+ Large Vacation Homes & Villas in or Near Southside
Modern & Spacious Mississippi River Retreat From US $269
         

9.8 (17 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Southside

Over 4+ Wheelchair Accessible Vacation Homes in or Near Southside
Motel 6-Prairie Du Chien, WI From US $50
         

6.0 (94 Reviews)
Hotel
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
Waterfront Hotel From US $129
         

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9.2 (896 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Waterfront Hotel From US $149
         

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New
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Comfort Inn & Suites Marquette - Prairie du Chien From US $86
         

8.8 (970 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV

Southside Vacation Rentals and Airbnb Places to Stay Under $200

Over 18+ Southside Vacation Rentals and Airbnb Places to Stay Under $200
Microtel Inn & Suites by Wyndham Prairie du Chien From US $83
         

8.0 (138 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Breakfast
Prairie Voyager From US $72
         

8.6 (125 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
The Great River Retreat From US $159
         

New
House
  • Air Conditioner
  • Parking
  • TV
Craftsman Cottage minutes from the Mississippi River. From US $185
         

Downtown Prairie du Chien Loft From US $179
         

9.2 (22 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety

Instantly Bookable Vacation Homes in Southside

Over 8+ Instantly Bookable Vacation Homes in or Near Southside
Cozy Alpine Retreat in Historic Downtown From US $151
         

10.0 (10 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Bluffside Chalet Suite From US $174
         

9.6 (4 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Prairie du Chien Home w/Yard: 3 Mi to River! From US $409
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
McGregor Condo w/Brewery On-Site: Steps to River! From US $346
         

10.0 (4 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Downtown McGregor Condo w/Restaurant On-Site! From US $407
         

8.0 (2 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Attractive apartment, directly across from winery! From US $120
         

New
Apartment
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety

About Southside Vacation Rentals

With more than 66 Southside vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Chartersbyowner 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 Southside.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Chartersbyowner Southside, 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 Southside. Places to stay near Southside are 392.16 ft² on average, with prices averaging $183 a night.

Chartersbyowner makes it easy and safe to find and compare vacation rentals in Southside 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 Southside

Type Count
Vacation Homes 25
Hotels with Suites 24
Holiday Apartments 8
Cabin Rentals 6
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Southside

Pro Tip: Chartersbyowner makes it easy to compare the best listings on Chartersbyowner homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Chartersbyowner 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 Southside.

Weather in Southside

View the weather forecast for Southside before booking your Southside 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 Southside, WI


Southside Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Southside?
How many vacation rentals are available in Southside?

Currently, the total number of properties listed in 2026 is over 66 in the Southside area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Southside.