Southwest Wisconsin, WI Vacation Homes from AED 453

Southwest Wisconsin Vacation Homes
Wisconsin
United States of America
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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 vacation 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 residential area with a large grassy yard, a yellow house, and a red garage.

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

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, (32 reviews)

10/10

Exceptional

(32 reviews)

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

Tammy

The price is AED 551

AED 551

AED 841 total

includes taxes & fees

2 Dec - 3 Dec

Hillsboro Driftless Guesthouse is cozy and ready for you!

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

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

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

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

2. 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, (99 reviews)

10/10

Exceptional

(99 reviews)

"Nice stay, will stay again."

Thomas D.

The price is AED 436

AED 436

AED 746 total

includes taxes & fees

8 Nov - 9 Nov

Ohio Street Retreat-hot tub, pool, massage chair

A field of lavender with a path leading through it.

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

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.

3. Tamarack Point Homestead

Tamarack Point Homestead

Arcadia

10.0 out of 10, Exceptional, (49 reviews)

10/10

Exceptional

(49 reviews)

"Nice quiet getaway."

RICHARD

The price is AED 386

AED 386

AED 453 total

includes taxes & fees

1 Dec - 2 Dec

Tamarack Point Homestead

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.

4. Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village

Wonewoc

10.0 out of 10, Exceptional, (16 reviews)

10/10

Exceptional

(16 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 AED 735

AED 735

AED 918 total

includes taxes & fees

2 Dec - 3 Dec

Colorful getaway in friendly Driftless village

A playground with various play structures, including a slide, swings, and climbing frames, surrounded by grass and trees.

A wooden cabin with a green door, a small porch, and a window.

A bathroom with a sink, wooden cabinets, a mirror, a window, and shelves with towels and toiletries.

A kitchen with wooden cabinets, a stove, a microwave, and a dishwasher.

5. River Road Getaway

River Road Getaway

Muscoda

9.6 out of 10, Exceptional, (42 reviews)

9.6/10

Exceptional

(42 reviews)

"Had everything we needed."

Tawnia

The price is AED 661

AED 661

AED 725 total

includes taxes & fees

2 Nov - 3 Nov

River Road Getaway

A breakfast setting with a table, chairs, plates, cutlery, glasses of orange juice, and a chocolate cake.

A bedroom with a bed, a dresser, a mirror, and a ceiling fan.

A hot tub with a towel and a bottle of Welch's, surrounded by greenery.

A modern kitchen with white cabinetry, a built-in microwave, and a central island with seating.

6. 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, (28 reviews)

9.8/10

Exceptional

(28 reviews)

"Kids loved all the board games and comfy seating options in the living room! Very comfortable stay."

Elizabeth N.

The price is AED 1,055

AED 1,055

AED 1,209 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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.

7. 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 AED 559

AED 559

AED 1,084 total

includes taxes & fees

2 Nov - 3 Nov

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

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

A kitchen with a large window, white tiles, and a black faucet.

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.

8. The Honey Haven

The Honey Haven

Westby

10.0 out of 10, Exceptional, (64 reviews)

10/10

Exceptional

(64 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

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

9. 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, (34 reviews)

9.8/10

Exceptional

(34 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 AED 514

AED 514

AED 942 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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.

10. Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point

Mineral Point

10.0 out of 10, Exceptional, (126 reviews)

10/10

Exceptional

(126 reviews)

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

Katie K.

The price is AED 565

AED 565

AED 811 total

includes taxes & fees

2 Nov - 3 Nov

Serenity Cottage at Mineral Point

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

11. 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 AED 540

AED 540

AED 2,273 total

includes taxes & fees

2 Nov - 3 Nov

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

A deck with a barbecue grill, a covered table, and a small covered area.

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

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

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 AED 349

AED 349

AED 814 total

includes taxes & fees

2 Nov - 3 Nov

Remodeled, cozy, pet friendly cabin near lakes

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

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

13. Dells Lake Villa - Lake Front Luxury

Dells Lake Villa - Lake Front Luxury

Lake Delton

9.6 out of 10, Exceptional, (15 reviews)

9.6/10

Exceptional

(15 reviews)

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

Mark V.

The price is AED 387

AED 387

AED 1,113 total

includes taxes & fees

2 Nov - 3 Nov

Dells Lake Villa - Lake Front Luxury

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 bedroom with a bed, a nightstand, a lamp, a ceiling fan, a dresser, and a large window.

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, (21 reviews)

9.6/10

Exceptional

(21 reviews)

"My friends and I enjoyed our stay here. "

Haily A.

The price is AED 348

AED 348

AED 1,065 total

includes taxes & fees

4 Nov - 5 Nov

Dells Paradise At Lighthouse Cove Condominiums

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.

15. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown

Downtown Trempealeau

9.8 out of 10, Exceptional, (108 reviews)

9.8/10

Exceptional

(108 reviews)

"Perfect place for a relaxing visit "

Lisa C.

The price is AED 459

AED 459

AED 557 total

includes taxes & fees

5 Nov - 6 Nov

The Bungaleau 1 Bedroom House In Cute Rivertown

A lakeside view with a gazebo, a round table, and a white picket fence.

A modern bedroom with a bed, a TV, a dresser, a fan, and a sliding glass door leading to a balcony.

A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a gray sofa and chairs.

A hallway with black tiled flooring, a grey rug, a decorative key hanging on the wall, and a ceiling light fixture.

16. Elegant Lake Home with Hot Tub

Elegant Lake Home with Hot Tub

Tomah

9.8 out of 10, Exceptional, (38 reviews)

9.8/10

Exceptional

(38 reviews)

"We loved our stay here! We would definitely book this house again if we come back to the area."

Delila M.

The price is AED 606

AED 606

AED 1,451 total

includes taxes & fees

11 Nov - 12 Nov

Elegant Lake Home with Hot Tub

A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

A bedroom with a bed, bedside tables, a window, and a door.

A modern living room with a blue sofa, a coffee table, and a dining area with chairs and a kitchen in the background.

A dining area with a large table, chairs, and potted plants.

17. Draper Vacation Home - Families & Friends Welcome

Draper Vacation Home - Families & Friends Welcome

Baraboo

10.0 out of 10, Exceptional, (50 reviews)

10/10

Exceptional

(50 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 AED 784

AED 784

AED 1,874 total

includes taxes & fees

2 Dec - 3 Dec

Draper Vacation Home - Families & Friends Welcome

A spacious living room with a grey sectional sofa, a glass coffee table, and a ceiling fan.

A modern kitchen with wooden cabinets, a central island, a stove, and a dishwasher.

A two-story house with a red roof, surrounded by dense forest, and a paved driveway leading to the front door.

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

18. 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.

Fawn Lake Cottage for Families Looking for Privacy

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.

19. 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 AED 377

AED 377

AED 887 total

includes taxes & fees

2 Nov - 3 Nov

Hamilton Goebel House 816 E Louisa St Darlington Wi

A two-story house with a red garage, a large front porch, and a well-lit exterior at dusk.

A pathway leading to a seating area with stone steps and a fire feature.

A modern spa area with a hot tub, wooden walls, and a staircase.

A two-story house with a covered porch, stone steps, and outdoor seating.

20. 5-Acre Luxury Chalet Near Wisconsin Dells Indoor/Outdoor Spa Suite Putting Green

5-Acre Luxury Chalet Near Wisconsin Dells Indoor/Outdoor Spa Suite Putting Green

Lyndon Station

9.8 out of 10, Exceptional, (97 reviews)

9.8/10

Exceptional

(97 reviews)

"Had a great time with family for week vacation! The property was excellent and the hosts were very helpful and super kind!"

Jaime T.

The price is AED 1,153

AED 1,153

AED 2,274 total

includes taxes & fees

11 Nov - 12 Nov

5-Acre Luxury Chalet Near Wisconsin Dells Indoor/Outdoor Spa Suite Putting Green

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

Natura Treescape Resort

10/10 Excellent

"Fantastic pool, friendly staff."

Shelley 2-night trip

Posted 1 hour ago

Natura Treescape Resort

Natura Vue Resort & Boathouse

10/10 Excellent

"L"

Jennifer 2-night trip

Posted 2 hours ago

Natura Vue Resort & Boathouse

Natura Aloha Reach Resort

10/10 Excellent

"Staying off-season has its benefits. We were the only ones on the beach taking a walk this morning. Resort was pretty quiet and it was a pleasant day."

Beatriz 1-night trip

Posted 2 hours ago

Natura Aloha Reach Resort

Mt. Olympus Water & Theme Park Resort

10/10 Excellent

"Ok"

Jorge 1-night trip

Posted 2 hours ago

Mt. Olympus Water & Theme Park Resort

The Madison Concourse Hotel and Governor's Club

8/10 Good

"The staff is excellent and the location is ideal. The property is just a little dated."

Kevin 3-night trip

Posted 4 hours ago

The Madison Concourse Hotel and Governor's Club

AmericInn by Wyndham Madison West

10/10 Excellent

"A very nice family hotel. Clean rooms. Good night's sleep. Good breakfast. Good hot tub & pool. Great staff."

Dee 2-night trip

Posted 21 hours ago

AmericInn by Wyndham Madison West

Amber's Inn & Suites

10/10 Excellent

"We always stay here hen visiting the Dells"

Majil 2-night trip

Posted 1 day ago

Amber's Inn & Suites

The Edgewater

10/10 Excellent

"We were engaged at the Edgewater a year ago and since then have been married so we decided to come back to spend our anniversary of our engagement back at the Edgewater where our love story all began ❤️thank you Edgewater for the memories"

Melissa 1-night trip

Posted 1 day ago

The Edgewater

Motel 6 Baraboo, WI - Lake Delton

8/10 Good

"Pricing good"

Tiffany 2-night trip

Posted 2 days ago

Motel 6 Baraboo, WI - Lake Delton

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Search Vacation Homes in Southwest Wisconsin

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Southwest Wisconsin vacation homes

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

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

3. Tamarack Point Homestead

4. Colorful getaway in friendly Driftless village

5. River Road Getaway

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

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

8. The Honey Haven

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

10. Serenity Cottage at Mineral Point

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

12. Remodeled, cozy, pet friendly cabin near lakes

13. Dells Lake Villa - Lake Front Luxury

14. Dells Paradise At Lighthouse Cove Condominiums

15. The Bungaleau 1 Bedroom House In Cute Rivertown

16. Elegant Lake Home with Hot Tub

17. Draper Vacation Home - Families & Friends Welcome

18. Fawn Lake Cottage for Families Looking for Privacy

19. Hamilton Goebel House 816 E Louisa St Darlington Wi

20. 5-Acre Luxury Chalet Near Wisconsin Dells Indoor/Outdoor Spa Suite Putting Green

Find vacation rentals that suit your style

Top Southwest Wisconsin Hotel Reviews

Natura Treescape Resort

Explore a world of travel with Expedia