Guest Houses in Southwest Wisconsin
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A lake surrounded by lush green hills and a rocky cliff.

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your current months are November, 2026 and December, 2026.

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Our top choices for Southwest Wisconsin guest houses

A park with picnic tables and chairs, a large tree, and a lake in the background.

A dining area with multiple wooden tables and chairs, large windows with a view of trees, and pendant lights.

A window with a view of a snowy outdoor area, including a red car and a small Christmas tree.

A room with a fireplace, a fan, and a framed picture on the wall.

1. Little Bluff Inn

Little Bluff Inn

2.5 star property

Downtown Trempealeau

10.0 out of 10, Exceptional, (177 reviews)

10/10

Exceptional

(177 reviews)

"Wonderful family run boutique hotel."

DAVID

The price is AU$152

AU$152

includes taxes & fees

10 Nov - 11 Nov

Little Bluff Inn

A Victorian-style house with a prominent front entrance, a steeply pitched roof, and a brick facade.

A spacious living room with two sofas, a coffee table, and a large chandelier.

A hallway with a chandelier, an exit sign, a chair, and a trash can.

A bedroom with a large bed, bedside lamps, a TV, and a window with curtains.

2. Mon Bijou

Mon Bijou

3.5 star property

Oconomowoc

9.4 out of 10, Exceptional, (10 reviews)

9.4/10

Exceptional

(10 reviews)

"This place is beautiful and well maintained. Every detail is well thought out. We did not know it was ladies night and there was a big event, so the music and noise was but loud until 10pm. 10pm is the start of quiet hours and it absolutely got quiet right at 10pm. The food and drinks from the bar and restaurant were execellent as well as the staff. We will be back!"

Zach

The price is AU$489

AU$489

includes taxes & fees

10 Nov - 11 Nov

Mon Bijou

A wooden deck with outdoor furniture, a view of the lake, and a railing.

A two-story house with a front porch, a fire escape, and a well-maintained garden with colorful flowers.

A cozy living room with a fireplace, wooden furniture, and a large window.

A wooden staircase with a handrail, leading to a room with a wooden door and a wall-mounted artwork.

3. Mendota Lake House Inn

Mendota Lake House Inn

3.0 star property

Downtown Madison

9.0 out of 10, Wonderful, (380 reviews)

9.0/10

Wonderful

(380 reviews)

"Super friendly owners!"

Nicholas

The price is AU$310

AU$310

includes taxes & fees

10 Nov - 11 Nov

Mendota Lake House Inn

A display of ceramic mugs and bowls on a table with a white tablecloth, illuminated by string lights.

A spacious room with a high ceiling, wooden beams, and a large window displaying a sign for The Rushford Inn.

A kitchen with wooden cabinets, a granite countertop, and a built-in microwave.

A cozy room with a red patterned armchair, a matching sofa, and a glass coffee table with magazines. A lamp and air conditioner are visible, along with a table displaying various items in the background.

4. The Rushford Inn

The Rushford Inn

3.0 star property

Rushford

9.4 out of 10, Exceptional, (10 reviews)

9.4/10

Exceptional

(10 reviews)

"Perfect location to have a reunion."

sonja

The price is AU$231

AU$231

includes taxes & fees

10 Nov - 11 Nov

The Rushford Inn

A hotel room with two beds, a nightstand, and two wall-mounted lamps.

A building with a sign reading 'The Sawmill Inn.' It has a brick facade, large windows, and a green roof.

A living room with a beige sofa, a small round table, a wicker chair, a floor lamp, and a framed photograph on the wall.

A compact bathroom with a sink, mirror, and a compact refrigerator.

5. The Sawmill Inn

The Sawmill Inn

3.0 star property

Houston

9.0 out of 10, Wonderful, (17 reviews)

9.0/10

Wonderful

(17 reviews)

"Loved the stay and location. The staff was helpful and assisted with early check in. Since we were going to an out of town wedding that was amazing for us."

Kimberly

The price is AU$223

AU$223

includes taxes & fees

10 Nov - 11 Nov

The Sawmill Inn

A historic building with a sign reading "American House 1854."

A row of buildings with distinct architectural styles, including a brick building labeled "American House 1854" and a wooden structure with a balcony.

A four-poster canopy bed with a dark wooden frame, a tufted headboard, and a plush grey bedspread. There is a wooden floor and a patterned rug in front of the bed.

A room with wooden flooring, a large mirror, and two upholstered chairs.

6. American House 1854- Stagecoach Stop Suite, 2 Bedrooms, Kitchenette, Sleeps 6

American House 1854- Stagecoach Stop Suite, 2 Bedrooms, Kitchenette, Sleeps 6

McGregor

10.0 out of 10, Exceptional, (31 reviews)

10/10

Exceptional

(31 reviews)

"Great location and clean place. Highly recommend"

Brad H.

The price is AU$413

AU$413

includes taxes & fees

10 Nov - 11 Nov

American House 1854- Stagecoach Stop Suite, 2 Bedrooms, Kitchenette, Sleeps 6

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Learn more about Southwest Wisconsin

Discover the family-friendly area of Southwest Wisconsin—water parks, festivals and top sights like Kalahari Indoor Waterpark.

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Kalahari Indoor Waterpark
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Pet-Friendly Holiday Packages French Island
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Visit Lyndon Station
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Madison Holidays
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Visit Wisconsin Dells
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Car hire near Madison
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Merrimac Holiday Rentals
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Search Southwest Wisconsin Guest Houses

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Southwest Wisconsin guest houses

1. Little Bluff Inn

2. Mon Bijou

3. Mendota Lake House Inn

4. The Rushford Inn

5. The Sawmill Inn

6. American House 1854- Stagecoach Stop Suite, 2 Bedrooms, Kitchenette, Sleeps 6

Learn more about Southwest Wisconsin

Explore a world of travel with Expedia