Southwest Wisconsin Holiday Houses

Southwest Wisconsin Holiday Homes
Wisconsin
United States of America
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 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 yellow house with a metal roof, a wooden deck, and a barbecue grill.

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

1. 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, (29 reviews)

10/10

Exceptional

(29 reviews)

"Nice place just outside city limits. Good spot to check out the area."

Dan G.

The price is NZ$376

NZ$376

includes taxes & fees

5 Oct - 6 Oct

Hillsboro Driftless Guesthouse is cozy and ready for you!

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

A covered porch with a wooden bench, a glass table, and white cushioned chairs.

2. 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 NZ$457

NZ$457

includes taxes & fees

27 Oct - 28 Oct

Colorful getaway in friendly Driftless village

A field of lavender with a path leading through it.

A kitchen with wooden cabinets, a stove, a sink, and a toaster.

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

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

3. 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 NZ$208

NZ$208

includes taxes & fees

7 Oct - 8 Oct

Tamarack Point Homestead

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

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

A living room with a sofa, a coffee table, and a patterned carpet. There is a doorway leading to a kitchen and dining area.

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

4. 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 NZ$285

NZ$285

includes taxes & fees

4 Oct - 5 Oct

The Bungaleau 1 Bedroom House In Cute Rivertown

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.

5. 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)

"Was a very nice and quiet place to relax and enjoy. Comfortable beds and very nice interior"

nate k.

The price is NZ$369

NZ$369

includes taxes & fees

1 Nov - 2 Nov

Ohio Street Retreat-hot tub, pool, massage chair

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

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

6. 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 NZ$415

NZ$415

includes taxes & fees

4 Oct - 5 Oct

Serenity Cottage at Mineral Point

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

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

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.

7. 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.

The price is NZ$877

NZ$877

includes taxes & fees

13 Oct - 14 Oct

Draper Vacation Home - Families & Friends Welcome

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

A window with a metal handle and a mesh screen, overlooking a grassy area with trees.

8. 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 NZ$408

NZ$408

includes taxes & fees

5 Oct - 6 Oct

Remodeled, cozy, pet friendly cabin near lakes

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

A grassy outdoor area with a circular arrangement of chairs around a fire pit, surrounded by trees and a fence.

9. Fawn Lake Cottage for Families Looking for Privacy

Fawn Lake Cottage for Families Looking for Privacy

Wisconsin Dells

9.8 out of 10, Exceptional, (11 reviews)

9.8/10

Exceptional

(11 reviews)

"Great home and host beautiful home "

Michael C.

The price is NZ$587

NZ$587

includes taxes & fees

4 Oct - 5 Oct

Fawn Lake Cottage for Families Looking for Privacy

A two-story house with a balcony, surrounded by a forest.

A wooden deck with a railing overlooking a forested area.

A forested area with a dirt path, a bench, and a lamp post.

A cozy attic bedroom with a wooden ceiling, a bed with a floral quilt, a chair, and a small Christmas tree.

10. Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.

Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.

Ontario

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"Really nice quiet place. Perfect for our hunting trip. "

Kolin C.

The price is NZ$634

NZ$634

includes taxes & fees

5 Oct - 6 Oct

Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.

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

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

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

11. 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)

"Up for 9 day hunt and visiting family and friends. Jay was very friendly and answered all requests. Location was very good for what we needed for our visit. Inside was well kept."

Roger S.

The price is NZ$532

NZ$532

includes taxes & fees

4 Oct - 5 Oct

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

An outdoor deck with a table and four chairs, overlooking a body of water and surrounded by bare trees.

A dining area with a table and chairs, a small cabinet, a ceiling fan, a window with curtains, and a door.

A modern living room with a brick wall, a flat-screen TV, a grey sofa, a coffee table, and a fireplace.

A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a sink.

12. Riverfront Twin Home

Riverfront Twin Home

La Crosse

10.0 out of 10, Exceptional, (62 reviews)

10/10

Exceptional

(62 reviews)

"Perfect place for a quick weekend getaway"

Jack H.

The price is NZ$543

NZ$543

includes taxes & fees

4 Oct - 5 Oct

Riverfront Twin Home

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

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

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

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

13. 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 NZ$446

NZ$446

includes taxes & fees

6 Oct - 7 Oct

Hamilton Goebel House 816 E Louisa St Darlington Wi

A spacious living area with a wooden dining table, a sofa, and a hanging chair. There are large windows providing natural light and a view of the outside.

A spacious hallway with a wooden floor, a brick wall on one side, and a dining area with a wooden table and chairs on the other.

A room with three large windows with white frames, brick walls, and a view of a clock tower and buildings.

A modern kitchen with dark cabinets, a central island with chairs, and a built-in oven.

14. MJ's Penthouse ,a piece of paradise on Monroe's historic square

MJ's Penthouse ,a piece of paradise on Monroe's historic square

Monroe

10.0 out of 10, Exceptional, (111 reviews)

10/10

Exceptional

(111 reviews)

"The Penthouse is beautiful and the location is unbeatable! We had a wonderful stay and can't wait to come back."

Andie

The price is NZ$484

NZ$484

includes taxes & fees

4 Oct - 5 Oct

MJ's Penthouse ,a piece of paradise on Monroe's historic square

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

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

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

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

15. Dells Lake Villa - Lake Front Luxury

Dells Lake Villa - Lake Front Luxury

Lake Delton

9.6 out of 10, Exceptional, (13 reviews)

9.6/10

Exceptional

(13 reviews)

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

Mark V.

The price is NZ$632

NZ$632

includes taxes & fees

26 Oct - 27 Oct

Dells Lake Villa - Lake Front Luxury

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.

16. Country home with flowing river

Country home with flowing river

Pardeeville

9.0 out of 10, Wonderful, (177 reviews)

9.0/10

Wonderful

(177 reviews)

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

Nate S.

The price is NZ$298

NZ$298

includes taxes & fees

5 Oct - 6 Oct

Country home with flowing river

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

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

A dining area with a wooden table and chairs, a bookshelf, and a leather couch.

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

17. 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.

The price is NZ$1,362

NZ$1,362

includes taxes & fees

13 Oct - 14 Oct

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

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

A two-story house with a garage, a stone chimney, and a well-lit entrance.

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.

18. 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, (32 reviews)

9.8/10

Exceptional

(32 reviews)

"A very unique place in a fantastic location! Little touches made our stay wonderful."

Mike L.

The price is NZ$441

NZ$441

includes taxes & fees

4 Oct - 5 Oct

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

A modern bar area with a large flat-screen TV displaying a beach scene, wooden cabinets, neon signs, and comfortable seating.

A modern kitchen with wooden cabinets, a built-in microwave, a coffee maker, and a toaster.

A modern bathroom with a glass shower door, a dark floor, and a white wall with a shelf holding toiletries.

A dining area with a rectangular table and six black chairs. There is a round mirror on the wall, a small shelf with decorative items, and a painting of a beach scene.

19. Bluff View Haven | Steps to Campus

Bluff View Haven | Steps to Campus

Holy Trinity-Longfellow

9.4 out of 10, Exceptional, (43 reviews)

9.4/10

Exceptional

(43 reviews)

"Walkable to grocery store, gas station and Restraunts which was super helpful since the rental car company was closed when we arrived at the airport due to our flight being delayed.Would definitely stay again"

Kim M.

The price is NZ$807

NZ$807

includes taxes & fees

19 Oct - 20 Oct

Bluff View Haven | Steps to Campus

A wooden deck with a table and chairs, surrounded by a wooden fence, overlooking a grassy area with trees.

A modern kitchen with grey cabinets, a stainless steel refrigerator, a built-in island with a sink, and a wooden chair.

A wooden cabin interior with a dining table and chairs, a kitchen area with a sink and cabinets, and large windows allowing natural light.

A wooden room with a skylight, a shower curtain, and a dark rug.

20. Charming 3-bedroom house with WiFi, AC in serene Necedah

Charming 3-bedroom house with WiFi, AC in serene Necedah

Necedah

9.8 out of 10, Exceptional, (20 reviews)

9.8/10

Exceptional

(20 reviews)

"We loved everything about this place."

Jessabelle

The price is NZ$719

NZ$719

includes taxes & fees

3 Oct - 4 Oct

Charming 3-bedroom house with WiFi, AC in serene Necedah

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

Baymont by Wyndham Madison West/Middleton WI West

10/10 Excellent

"The property was clean and the building was cleaned regularly."

Jennifer 3-night trip

Posted 4 hours ago

Baymont by Wyndham Madison West/Middleton WI West

Best Western Baraboo Inn

8/10 Good

"Everything was excellent except the fact that indoor pool was closed for renovation. If we knew that we could choose another hotel in area with pool working, but that information was not online when we booked."

Michael 2-night trip

Posted 5 hours ago

Best Western Baraboo Inn

AmericInn by Wyndham Madison West

10/10 Excellent

"We make an annual trip to Madison, and we always stay in the AmericInn. It is affordable, dependably clean, and has a tasty breakfast with good variety."

Laurie 2-night trip

Posted 5 hours ago

AmericInn by Wyndham Madison West

Natura Aloha Reach Resort

8/10 Good

"Get rid of the geese and buzzards."

Michael 2-night trip

Posted 6 hours ago

Natura Aloha Reach Resort

Natura Vue Resort & Boathouse

8/10 Good

"The room was very clean, and had lots of room. I would have liked the tub and shower to have better water pressure. All in all it was a great place to stay and was close to bars,gas station,and grocery store plus all the shops on the main street."

Wallace 2-night trip

Posted 1 day ago

Natura Vue Resort & Boathouse

Dellshire Resort

10/10 Excellent

"Great new hotel."

Rada 2-night trip

Posted 1 day ago

Dellshire Resort

Stoney Creek Hotel La Crosse - Onalaska

8/10 Good

"."

Sherry 1-night trip

Posted 1 day ago

Stoney Creek Hotel La Crosse - Onalaska

The Edgewater

10/10 Excellent

"The Edgewater is one of my favorite hotels. I had such a wonderful stay and always enjoy being here. I’ll definitely be back!"

Stacy 2-night trip

Posted 1 day ago

The Edgewater

Natura Treescape Resort

8/10 Good

"we loved our cabin the pool, sauna, and hottub plus we got free tickets for the zoo which was wonderful."

REBECA 1-night trip

Posted 2 days ago

Natura Treescape Resort

Find out more about Southwest Wisconsin

Southwest Wisconsin Holiday Homes information

Number of reviews	960
Accommodation	602 Holiday Homes
Lowest Price	NZ$208
Highest Price	NZ$1,362

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Book Holiday Homes in Southwest Wisconsin on Expedia.com

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. Hillsboro Driftless Guesthouse is cozy and ready for you!

2. Colorful getaway in friendly Driftless village

3. Tamarack Point Homestead

4. The Bungaleau 1 Bedroom House In Cute Rivertown

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

6. Serenity Cottage at Mineral Point

7. Draper Vacation Home - Families & Friends Welcome

8. Remodeled, cozy, pet friendly cabin near lakes

9. Fawn Lake Cottage for Families Looking for Privacy

10. Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.

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

12. Riverfront Twin Home

13. Hamilton Goebel House 816 E Louisa St Darlington Wi

14. MJ's Penthouse ,a piece of paradise on Monroe's historic square

15. Dells Lake Villa - Lake Front Luxury

16. Country home with flowing river

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

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

19. Bluff View Haven | Steps to Campus

20. Charming 3-bedroom house with WiFi, AC in serene Necedah

Find holiday rentals that suit your style

Top Southwest Wisconsin Hotel Reviews

Baymont by Wyndham Madison West/Middleton WI West

Find out more about Southwest Wisconsin

Southwest Wisconsin Holiday Homes information

Explore a world of travel with Expedia