A lake surrounded by lush green hills and a rocky cliff.

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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.

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)
"The property is very well maintained, house was very cozy and relaxing. The host was great to communicate with."
United States
Tammy
The price is AED 496
AED 818 total
includes taxes & fees
2 Nov - 3 Nov
Hillsboro Driftless Guesthouse is cozy and ready for you!
A bedroom with a vanity, a large mirror, a bed, and a nightstand with a lamp.

2. 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)
"A lovely location, and the lodging was quite comfortable and enjoyable to spend time in. We hope to be able to return."
United States
Mike G.
The price is AED 514
AED 980 total
includes taxes & fees
1 Nov - 2 Nov
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
A playground with various play structures, including a slide, swings, and climbing frames, surrounded by grass and trees.

3. River Road Getaway

River Road Getaway
Muscoda
9.6 out of 10, Exceptional, (42 reviews)
"Had everything we needed."
United States
Tawnia
The price is AED 661
AED 798 total
includes taxes & fees
1 Nov - 2 Nov
River Road Getaway
A single-story house with a gabled roof, a front porch, and a small front yard with mulch and plants.

4. Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village
Wonewoc
10.0 out of 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!"
United States
Emily B.
The price is AED 735
AED 961 total
includes taxes & fees
1 Nov - 2 Nov
Colorful getaway in friendly Driftless village
A modern kitchen with a central island, stainless steel appliances, and wooden flooring.

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, (99 reviews)
"Nice stay, will stay again."
United States
Thomas D.
The price is AED 436
AED 787 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.

6. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (49 reviews)
"Nice quiet getaway."
United States
RICHARD
The price is AED 366
AED 433 total
includes taxes & fees
1 Nov - 2 Nov
Tamarack Point Homestead
A breakfast setting with a table, chairs, plates, cutlery, glasses of orange juice, and a chocolate cake.

7. 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)
"Kids loved all the board games and comfy seating options in the living room! Very comfortable stay."
United States
Elizabeth N.
The price is AED 2,016
AED 2,429 total
includes taxes & fees
13 Nov - 14 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.

8. 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)
"This unit was conveniently located, clean and well appointed. The host was friendly and helpful. Had a great time!"
United States
Gerard B.
The price is AED 559
AED 1,197 total
includes taxes & fees
1 Nov - 2 Nov
Large 2-bedroom lower unit with fast WI-FI & in unit washer/dryer
Living area

9. Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (126 reviews)
"Super cute and cozy place - perfect for our getaway. "
United States
Katie K.
Serenity Cottage at Mineral Point
A hallway with a wooden door leading to a kitchen area.

10. 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)
"Excellent house and fun for the whole family! We can’t wait to stay again!"
United States
Cristin S.
The price is AED 540
AED 2,506 total
includes taxes & fees
1 Nov - 2 Nov
Cozy Luxe Retreat| High-End Design w/outdoor fire pit WI Dells, Cascade MT, Devils Lake
A modern living room with a staircase, a dark door, a grey armchair, and a coffee table with decorative items.

11. The Honey Haven

The Honey Haven
Westby
10.0 out of 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."
United States
Eric R.
The price is AED 617
AED 965 total
includes taxes & fees
16 Nov - 17 Nov
The Honey Haven
An outdoor deck with a table and four chairs, overlooking a body of water and surrounded by bare trees.

12. Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (66 reviews)
"Perfect place for a quick weekend getaway"
United States
Jack H.
The price is AED 496
AED 1,119 total
includes taxes & fees
1 Nov - 2 Nov
Riverfront Twin Home
Property grounds

13. Remodeled, cozy, pet friendly cabin near lakes

Remodeled, cozy, pet friendly cabin near lakes
Necedah
10.0 out of 10, Exceptional, (39 reviews)
"This is a cute little place out in the country. Communication with the hostess was good."
United States
Dawn
The price is AED 349
AED 853 total
includes taxes & fees
2 Nov - 3 Nov
Remodeled, cozy, pet friendly cabin near lakes
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

14. Draper Vacation Home - Families & Friends Welcome

Draper Vacation Home - Families & Friends Welcome
Baraboo
10.0 out of 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."
United States
Michele T.
The price is AED 780
AED 1,869 total
includes taxes & fees
1 Nov - 2 Nov
Draper Vacation Home - Families & Friends Welcome
A wooden deck with a table and chairs, surrounded by a wooden fence, overlooking a grassy area with trees.

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

Charming 3-bedroom house with WiFi, AC in serene Necedah
Necedah
10.0 out of 10, Exceptional, (21 reviews)
"We loved everything about this place."
United States
Jessabelle
The price is AED 514
AED 1,507 total
includes taxes & fees
31 Oct - 1 Nov
Charming 3-bedroom house with WiFi, AC in serene Necedah
A wooden deck with a bench, a white door, and hanging flower baskets.

16. 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)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is AED 459
AED 589 total
includes taxes & fees
5 Nov - 6 Nov
The Bungaleau 1 Bedroom House In Cute Rivertown
A covered outdoor area with a table and chairs, a view of a lake, and docked boats.

17. Dells Lake Villa - Lake Front Luxury

Dells Lake Villa - Lake Front Luxury
Lake Delton
9.6 out of 10, Exceptional, (15 reviews)
"Nice property and close to many of the Dells attractions."
United States
Mark V.
The price is AED 387
AED 1,113 total
includes taxes & fees
1 Nov - 2 Nov
Dells Lake Villa - Lake Front Luxury
A multi-story hotel with a pool area and a beach.

18. Dells Paradise At Lighthouse Cove Condominiums

Dells Paradise At Lighthouse Cove Condominiums
Lake Delton
9.6 out of 10, Exceptional, (21 reviews)
"My friends and I enjoyed our stay here. "
United States
Haily A.
Dells Paradise At Lighthouse Cove Condominiums
A lakeside view with a gazebo, a round table, and a white picket fence.

19. Elegant Lake Home with Hot Tub

Elegant Lake Home with Hot Tub
Tomah
9.8 out of 10, Exceptional, (38 reviews)
"We loved our stay here! We would definitely book this house again if we come back to the area."
United States
Delila M.
The price is AED 606
AED 1,526 total
includes taxes & fees
1 Nov - 2 Nov
Elegant Lake Home with Hot Tub
A serene park with a pond, lush green grass, and a house in the background.

20. Country home with flowing river

Country home with flowing river
Pardeeville
9.0 out of 10, Wonderful, (180 reviews)
"Great stay and a wonderful property, look forward to staying again"
United States
Nate S.
The price is AED 511
AED 616 total
includes taxes & fees
1 Nov - 2 Nov
Country home with flowing river
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

Baymont by Wyndham Madison West/Middleton WI West

8/10 Good
"Very nice staff."
Diana 2-night trip
Posted 3 hours ago
Baymont by Wyndham Madison West/Middleton WI West

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