Southwest Wisconsin Holiday Homes from €109: Search Top House Rentals

Southwest Wisconsin Holiday Homes
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A lake surrounded by lush green hills and a rocky cliff.

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Our top choices for Southwest Wisconsin holiday homes

A field of lavender with a path leading through it.

A living room with a brown leather sofa, a black ottoman, a TV on a stand, and a framed picture on the wall.

A rustic wooden structure with a small shed, surrounded by a well-maintained grassy field and a tree.

A rural landscape with a barn, a small house, and a large house with a porch.

1. Tamarack Point Homestead

Tamarack Point Homestead

Arcadia

10.0 out of 10, Exceptional, (46 reviews)

10/10

Exceptional

(46 reviews)

"Brady was very prompt and the stay exceeded expectations We plan to stay again very soon! Thank you, Brady!"

Josias F.

The price is €109

€109

includes taxes & fees

14 Oct - 15 Oct

Tamarack Point Homestead

A living room with a television, a coffee table, a sofa, and a dining area in the background.

A living room with a television, a sofa, a coffee table with magazines, and a kitchen in the background.

A bedroom with a bed, bedside table, lamp, and a bench with a cushion.

A yellow house with a metal roof, a wooden deck, and a barbecue grill.

2. Hillsboro Driftless Guesthouse is cozy and ready for you!

Hillsboro Driftless Guesthouse is cozy and ready for you!

Hillsboro

10.0 out of 10, Exceptional, (31 reviews)

10/10

Exceptional

(31 reviews)

"The property is very well maintained, house was very cozy and relaxing. The host was great to communicate with."

Tammy

The price is €201

€201

includes taxes & fees

19 Oct - 20 Oct

Hillsboro Driftless Guesthouse is cozy and ready for you!

A modern kitchen with a central island, stainless steel appliances, and wooden flooring.

A black massage chair in a room with a wooden table and a carpeted floor.

A wooden deck with outdoor furniture including a table and chairs.

A bedroom with a bed, a headboard, a wall-mounted lamp, and a ceiling light fixture.

3. Ohio Street Retreat-hot tub, pool, massage chair

Ohio Street Retreat-hot tub, pool, massage chair

Prairie du Chien

10.0 out of 10, Exceptional, (95 reviews)

10/10

Exceptional

(95 reviews)

"Nice stay, will stay again."

Thomas D.

The price is €189

€189

includes taxes & fees

1 Nov - 2 Nov

Ohio Street Retreat-hot tub, pool, massage chair

A bedroom with a vanity, a large mirror, a bed, and a nightstand with a lamp.

Two wicker chairs with striped cushions and a small table with a vase of flowers.

A kitchen with white cabinets, a black countertop, and a patterned rug. There is a microwave, toaster, and a coffee maker on the counter.

4. The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

Mount Horeb

9.8 out of 10, Exceptional, (33 reviews)

9.8/10

Exceptional

(33 reviews)

"A lovely location, and the lodging was quite comfortable and enjoyable to spend time in. We hope to be able to return."

Mike G.

The price is €231

€231

includes taxes & fees

18 Oct - 19 Oct

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

A single-story house with a gabled roof, a front porch, and a small front yard with mulch and plants.

A dining area with a wooden table, chairs, and a patterned rug. There is a wooden cabinet with glass doors on the left, and a chair with a cushion on the right.

A kitchen with a stove, oven, and various kitchen utensils. There is a window with curtains, a ceiling fan, and a green rug.

A spacious living room with a wooden floor, a sofa, a coffee table, and a dining area with a table and chairs.

5. Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village

Wonewoc

10.0 out of 10, Exceptional, (15 reviews)

10/10

Exceptional

(15 reviews)

"Sweet home! Loved all the bright colored decorations! We had a great stay here with our bikes and pups. The porch was lovely to watch a thunderstorm from as well!"

Emily B.

The price is €238

€238

includes taxes & fees

14 Oct - 15 Oct

Colorful getaway in friendly Driftless village

A living room with a TV, wooden furniture, a dining table with chairs, and a kitchen in the background.

A furnished living room with a wooden coffee table, a grey sofa, a beige armchair, and a dining table with chairs.

A compact kitchen with wooden cabinets, a stove, a refrigerator, and a dining area with a table and chairs.

A bedroom with a bed, two bedside tables, a ceiling light, a door, and two windows with blinds.

6. Large 2-bedroom lower unit with fast WI-FI & in unit washer/dryer

Large 2-bedroom lower unit with fast WI-FI & in unit washer/dryer

Baraboo

9.8 out of 10, Exceptional, (8 reviews)

9.8/10

Exceptional

(8 reviews)

"This unit was conveniently located, clean and well appointed. The host was friendly and helpful. Had a great time!"

Gerard B.

The price is €289

€289

includes taxes & fees

14 Oct - 15 Oct

Large 2-bedroom lower unit with fast WI-FI & in unit washer/dryer

A white house with a covered patio, a sliding glass door, and a small table.

A dining room with a large wooden table and chairs, a fireplace, and a mirror reflecting the room.

A living room with two sofas, a TV, and a wooden door.

7. Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point

Mineral Point

10.0 out of 10, Exceptional, (123 reviews)

10/10

Exceptional

(123 reviews)

"Super cute and cozy place - perfect for our getaway. "

Katie K.

The price is €208

€208

includes taxes & fees

19 Oct - 20 Oct

Serenity Cottage at Mineral Point

A wooden deck with a bench, a white door, and hanging flower baskets.

A residential house with a front porch, a small garden with orange flowers, and a red building in the background.

A bedroom with a wooden bed frame, a quilt, a window with a view of a waterfall, and a ceiling fan.

A single-story house with a front door, a mailbox, and a small window.

8. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown

Downtown Trempealeau

9.8 out of 10, Exceptional, (105 reviews)

9.8/10

Exceptional

(105 reviews)

"Perfect place for a relaxing visit "

Lisa C.

The price is €147

€147

includes taxes & fees

25 Oct - 26 Oct

The Bungaleau 1 Bedroom House In Cute Rivertown

A kitchen with a sliding glass door leading to a wooden deck with a view of a grassy field and a lake.

A playground with slides and climbing structures near a lake.

A two-story house with a wooden deck and a staircase leading to the upper level.

A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

9. Updated home with lake views, across the street from Lake WI, near free ferry

Updated home with lake views, across the street from Lake WI, near free ferry

Merrimac

10.0 out of 10, Exceptional, (47 reviews)

10/10

Exceptional

(47 reviews)

"Very clean property, exactly as advertised. Host was easy to work with."

Jacob M.

The price is €300

€300

includes taxes & fees

14 Oct - 15 Oct

Updated home with lake views, across the street from Lake WI, near free ferry

A modern living room with a staircase, a dark door, a grey armchair, and a coffee table with decorative items.

A dining area with a wooden table and chairs, a white door, and a kitchen with cabinets and appliances.

A living room with a sofa, armchairs, a coffee table, and a window.

A building with a covered porch, a dark door, and two potted plants.

10. The Honey Haven

The Honey Haven

Westby

10.0 out of 10, Exceptional, (62 reviews)

10/10

Exceptional

(62 reviews)

"This was my second time staying at the Honey Haven and I would love to stay again. The host does a wonderful job keeping the property in great shape and the area that the property is in is so special."

Eric R.

The Honey Haven

An aerial view of a golf course with a wedding ceremony in progress.

A modern kitchen with white cabinets, stainless steel appliances, and a window providing natural light.

A modern living room with a sofa set, a coffee table, and a television.

An aerial view of a golf course with a pond, trees, and distant buildings.

11. KwikStay: Spacious 5BR Townhome Near Spring Green Golf Course & Park

KwikStay: Spacious 5BR Townhome Near Spring Green Golf Course & Park

Spring Green

9.8 out of 10, Exceptional, (27 reviews)

9.8/10

Exceptional

(27 reviews)

"This was a nice stay for us. House is in a nice, quiet neighborhood."

Gretchen P.

The price is €325

€325

includes taxes & fees

14 Oct - 15 Oct

KwikStay: Spacious 5BR Townhome Near Spring Green Golf Course & Park

A wooden deck with wicker furniture and a table, overlooking a forested area.

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

12. Remodeled, cozy, pet friendly cabin near lakes

Remodeled, cozy, pet friendly cabin near lakes

Necedah

10.0 out of 10, Exceptional, (39 reviews)

10/10

Exceptional

(39 reviews)

"This is a cute little place out in the country. Communication with the hostess was good."

Dawn

The price is €210

€210

includes taxes & fees

15 Oct - 16 Oct

Remodeled, cozy, pet friendly cabin near lakes

A hallway with a wooden door leading to a kitchen area.

A bedroom with a large bed, a nightstand, a chair, and a chandelier.

A two-story white house with a steeply pitched roof, a front porch with a red staircase, and a small garden area.

A modern kitchen with white cabinets, a central island with stools, a stainless steel stove, and a hanging light fixture.

13. Cozy Luxe Retreat| High-End Design w/outdoor fire pit WI Dells, Cascade MT, Devils Lake

Cozy Luxe Retreat| High-End Design w/outdoor fire pit WI Dells, Cascade MT, Devils Lake

Baraboo

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"Excellent house and fun for the whole family! We can’t wait to stay again!"

Cristin S.

Cozy Luxe Retreat| High-End Design w/outdoor fire pit WI Dells, Cascade MT, Devils Lake

A multi-story hotel with a pool area and a beach.

A lakeside picnic area with wooden benches and picnic tables, surrounded by a stone walkway.

A modern living room with a grey sofa, a dining area with a wooden table and chairs, and a kitchen with white cabinets and a central island.

A lakeside beach with lounge chairs and a dock with boats.

14. Dells Paradise At Lighthouse Cove Condominiums

Dells Paradise At Lighthouse Cove Condominiums

Lake Delton

9.6 out of 10, Exceptional, (20 reviews)

9.6/10

Exceptional

(20 reviews)

"My friends and I enjoyed our stay here. "

Haily A.

The price is €290

€290

includes taxes & fees

21 Oct - 22 Oct

Dells Paradise At Lighthouse Cove Condominiums

A covered outdoor area with a table and chairs, a view of a lake, and docked boats.

A living room with a fireplace, a sofa, a TV, and a ceiling fan.

A lakeside beach with white lounge chairs and a dock with boats.

A modern kitchen with dark wood cabinets, stainless steel appliances, a large island with stools, and a decorative sign on the wall.

15. Dells Lake Villa - Lake Front Luxury

Dells Lake Villa - Lake Front Luxury

Lake Delton

9.6 out of 10, Exceptional, (14 reviews)

9.6/10

Exceptional

(14 reviews)

"Nice property and close to many of the Dells attractions."

Mark V.

The price is €313

€313

includes taxes & fees

18 Oct - 19 Oct

Dells Lake Villa - Lake Front Luxury

A two-story house with a deck, outdoor seating area, and a fire pit.

A residential area with houses, a dock, and a small pond.

A modern living room with a fireplace, wooden accents, and a dining area with bar stools.

A dining area with a wooden table and metal chairs, a shelf with decorative items, and a window with a view of greenery.

16. Serene Castle Rock Cabin w/Hot Tub

Serene Castle Rock Cabin w/Hot Tub

Mauston

9.8 out of 10, Exceptional, (10 reviews)

9.8/10

Exceptional

(10 reviews)

"Place was very clean and there were beautiful sunsets!"

Catherine K.

The price is €478

€478

includes taxes & fees

14 Oct - 15 Oct

Serene Castle Rock Cabin w/Hot Tub

A single-story house with a front porch, a garage, and a small shed in a grassy yard surrounded by trees.

A bedroom with a bed, a ceiling fan, a TV, a window with curtains, and a wall clock.

A kitchen with wooden cabinets, a stove, a dishwasher, and a backsplash with a rooster design.

A playroom with a concrete floor, a window, and various children's play equipment.

17. Fawn Lake Cottage for Families Looking for Privacy

Fawn Lake Cottage for Families Looking for Privacy

Wisconsin Dells

9.8 out of 10, Exceptional, (12 reviews)

9.8/10

Exceptional

(12 reviews)

"Great home and host beautiful home "

Michael C.

The price is €302

€302

includes taxes & fees

14 Oct - 15 Oct

Fawn Lake Cottage for Families Looking for Privacy

A bedroom with a bed, a television mounted on the wall, a window with blinds, and a closet with shelves.

A modern kitchen with a stainless steel refrigerator, a microwave, and a coffee maker. There are hanging utensils and a decorative plate rack on the wall.

A billiards room with a pool table, foosball table, and ping pong table.

18. Draper Vacation Home - Families & Friends Welcome

Draper Vacation Home - Families & Friends Welcome

Baraboo

10.0 out of 10, Exceptional, (49 reviews)

10/10

Exceptional

(49 reviews)

"It was a great place to rent for a weekend with the family. We were able to bring our dog too so that was amazing. The house was clean and it had everything you needed for toiletries, kitchen, board games, grill etc."

Michele T.

Draper Vacation Home - Families & Friends Welcome

A serene park with a pond, lush green grass, and a house in the background.

A living room with a sofa, armchair, wooden coffee table, and a fireplace.

A living room with a blue sofa, a black leather armchair, a fireplace, and a television mounted on the wall.

A pool table with balls and cues, surrounded by shelves and a staircase.

19. Country home with flowing river

Country home with flowing river

Pardeeville

9.0 out of 10, Wonderful, (178 reviews)

9.0/10

Wonderful

(178 reviews)

"Great stay and a wonderful property, look forward to staying again"

Nate S.

The price is €154

€154

includes taxes & fees

1 Nov - 2 Nov

Country home with flowing river

A family standing in front of a stone building with a wooden porch and a number '816' above the entrance.

A kitchen with white cabinets, a granite countertop, and a stone wall.

A dining area with a wooden table and chairs, a stone wall, and a kitchen in the background.

A bedroom with a wooden bed, a nightstand with a lamp, a window with blinds, and a wooden floor.

20. Hamilton Goebel House 816 E Louisa St Darlington Wi

Hamilton Goebel House 816 E Louisa St Darlington Wi

Darlington

9.8 out of 10, Exceptional, (54 reviews)

9.8/10

Exceptional

(54 reviews)

"Three couples stayed at this property. Very comfy beds. We all enjoyed our stay and already have plans to stay again in the fall. It is also close to the trails."

Danette M.

The price is €222

€222

includes taxes & fees

19 Oct - 20 Oct

Hamilton Goebel House 816 E Louisa St Darlington Wi

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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Top Southwest Wisconsin Hotel Reviews

DoubleTree by Hilton Madison Downtown

10/10 Excellent

"Was nice and good location"

Jenn 1-night trip

Posted 2 hours ago

DoubleTree by Hilton Madison Downtown

Natura Treescape Resort

8/10 Good

"Nice location"

Daniel 2-night trip

Posted 4 hours ago

Natura Treescape Resort

AmericInn by Wyndham Madison West

8/10 Good

"The shower curtain is about 1-2 in above the ground. It's right over the lip to outside the tub. Water from the shower dripped on the curtain and onto the floor and created a puddle"

Frank 4-night trip

Posted 4 hours ago

AmericInn by Wyndham Madison West

Natura Vue Resort & Boathouse

10/10 Excellent

"Clean rooms, beautiful view, nice staff we love it"

Julia 1-night trip

Posted 4 hours ago

Natura Vue Resort & Boathouse

The Edgewater

10/10 Excellent

"We've stayed at the Edgewater a couple times & it is definitely our first choice whenever we visit Madison. Beautiful location, clean and luxurious hotel, great food, and a very friendly staff. What's not to love?"

Mary 1-night trip

Posted 5 hours ago

The Edgewater

Staybridge Suites Wisconsin Dells - Lake Delton by IHG

10/10 Excellent

"Great property with enough to do on site. Walkable places to eat nearby. I’d stay here again."

Cynthia 3-night trip

Posted 5 hours ago

Staybridge Suites Wisconsin Dells - Lake Delton by IHG

Amber's Inn & Suites

10/10 Excellent

"Na"

IVAN 2-night trip

Posted 9 hours ago

Amber's Inn & Suites

Dellshire Resort

10/10 Excellent

"A very good place to spend a weekend, the facilities look new, the staff very friendly. Everything was very clean. I would go again in a short time."

Olmary 2-night trip

Posted 9 hours ago

Dellshire Resort

Grand Marquis Waterpark Hotel & Suites

10/10 Excellent

"Only stayed one night good location easy off and back on the interstate. Nice"

SUSAN 1-night trip

Posted 1 day ago

Grand Marquis Waterpark Hotel & Suites

Find out more about Southwest Wisconsin

Southwest Wisconsin Holiday Homes information

Number of reviews	748
Accommodation	591 Holiday Homes
Lowest Price	€109
Highest Price	€478

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Holiday Homes in Southwest Wisconsin

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Southwest Wisconsin holiday homes

1. Tamarack Point Homestead

2. Hillsboro Driftless Guesthouse is cozy and ready for you!

3. Ohio Street Retreat-hot tub, pool, massage chair

4. The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

5. Colorful getaway in friendly Driftless village

6. Large 2-bedroom lower unit with fast WI-FI & in unit washer/dryer

7. Serenity Cottage at Mineral Point

8. The Bungaleau 1 Bedroom House In Cute Rivertown

9. Updated home with lake views, across the street from Lake WI, near free ferry

10. The Honey Haven

11. KwikStay: Spacious 5BR Townhome Near Spring Green Golf Course & Park

12. Remodeled, cozy, pet friendly cabin near lakes

13. Cozy Luxe Retreat| High-End Design w/outdoor fire pit WI Dells, Cascade MT, Devils Lake

14. Dells Paradise At Lighthouse Cove Condominiums

15. Dells Lake Villa - Lake Front Luxury

16. Serene Castle Rock Cabin w/Hot Tub

17. Fawn Lake Cottage for Families Looking for Privacy

18. Draper Vacation Home - Families & Friends Welcome

19. Country home with flowing river

20. Hamilton Goebel House 816 E Louisa St Darlington Wi

Find holiday rentals that suit your style

Top Southwest Wisconsin Hotel Reviews

DoubleTree by Hilton Madison Downtown

Find out more about Southwest Wisconsin

Southwest Wisconsin Holiday Homes information

Explore a world of travel with Expedia