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

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 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, (31 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
26 Oct - 27 Oct
Hillsboro Driftless Guesthouse is cozy and ready for you!
A field of lavender with a path leading through it.

2. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (47 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveler
The price is AED 335
AED 431 total
includes taxes & fees
22 Oct - 23 Oct
Tamarack Point Homestead
A modern kitchen with a central island, stainless steel appliances, and wooden flooring.

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)
"Nice stay, will stay again."
United States
Thomas D.
The price is AED 436
AED 787 total
includes taxes & fees
1 Nov - 2 Nov
Ohio Street Retreat-hot tub, pool, massage chair
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, (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!"
United States
Emily B.
The price is AED 735
AED 961 total
includes taxes & fees
21 Oct - 22 Oct
Colorful getaway in friendly Driftless village
A bedroom with a vanity, a large mirror, a bed, and a nightstand with a lamp.

5. 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 477
AED 926 total
includes taxes & fees
21 Oct - 22 Oct
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Living area

6. Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (125 reviews)
"Super cute and cozy place - perfect for our getaway. "
United States
Katie K.
The price is AED 551
AED 837 total
includes taxes & fees
27 Oct - 28 Oct
Serenity Cottage at Mineral Point
A living room with a TV, wooden furniture, a dining table with chairs, and a kitchen in the background.

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)
"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
21 Oct - 22 Oct
Large 2-bedroom lower unit with fast WI-FI & in unit washer/dryer
A breakfast setting with a table, chairs, plates, cutlery, glasses of orange juice, and a chocolate cake.

8. 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)
"The host is a pleasure to work with. The house worked great for our needs. Thank you!"
United States
David A.
The price is AED 1,151
AED 1,389 total
includes taxes & fees
25 Oct - 26 Oct
KwikStay: Spacious 5BR Townhome Near Spring Green Golf Course & Park
A modern living room with a staircase, a dark door, a grey armchair, and a coffee table with decorative items.

9. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (63 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 588
AED 930 total
includes taxes & fees
21 Oct - 22 Oct
The Honey Haven
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
21 Oct - 22 Oct
Cozy Luxe Retreat| High-End Design w/outdoor fire pit WI Dells, Cascade MT, Devils Lake
A wooden deck with a bench, a white door, and hanging flower baskets.

11. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (106 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is AED 459
AED 589 total
includes taxes & fees
25 Oct - 26 Oct
The Bungaleau 1 Bedroom House In Cute Rivertown
Property grounds

12. 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
22 Oct - 23 Oct
Remodeled, cozy, pet friendly cabin near lakes
A family standing in front of a stone building with a wooden porch and a number '816' above the entrance.

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)
"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."
United States
Danette M.
The price is AED 377
AED 931 total
includes taxes & fees
28 Oct - 29 Oct
Hamilton Goebel House 816 E Louisa St Darlington Wi
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 590
AED 1,720 total
includes taxes & fees
21 Oct - 22 Oct
Draper Vacation Home - Families & Friends Welcome
A covered outdoor area with a table and chairs, a view of a lake, and docked boats.

15. Dells Lake Villa - Lake Front Luxury

Dells Lake Villa - Lake Front Luxury
Lake Delton
9.6 out of 10, Exceptional, (14 reviews)
"Nice property and close to many of the Dells attractions."
United States
Mark V.
The price is AED 480
AED 1,287 total
includes taxes & fees
28 Oct - 29 Oct
Dells Lake Villa - Lake Front Luxury
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.

16. 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, (114 reviews)
"The Penthouse is beautiful and the location is unbeatable! We had a wonderful stay and can't wait to come back."
United States
Andie
The price is AED 716
AED 997 total
includes taxes & fees
21 Oct - 22 Oct
MJ's Penthouse ,a piece of paradise on Monroe's historic square
A serene lakeside setting with a wooden dock extending into the water, surrounded by lush greenery and trees.

17. Lake Cottage 30 minutes from Wisconsin Dells.

Lake Cottage 30 minutes from Wisconsin Dells.
Friendship
9.8 out of 10, Exceptional, (64 reviews)
"The whole process from rental to leaving was simple. Loved the two docks available to fish from (front and rear of the cottage). Husband loved that there was kayaks , canoe l, and row boat available to get out on the lake. Home was very inviting and home like. Would definitely stay again!"
United States
Rebecca L.
The price is AED 386
AED 1,132 total
includes taxes & fees
23 Oct - 24 Oct
Lake Cottage 30 minutes from Wisconsin Dells.
An outdoor deck with a table and four chairs, overlooking a body of water and surrounded by bare trees.

18. 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 1,128 total
includes taxes & fees
21 Oct - 22 Oct
Riverfront Twin Home
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 643
AED 1,572 total
includes taxes & fees
11 Nov - 12 Nov
Elegant Lake Home with Hot Tub
A multi-story hotel with a pool area and a beach.

20. 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.
The price is AED 410
AED 1,205 total
includes taxes & fees
21 Oct - 22 Oct
Dells Paradise At Lighthouse Cove Condominiums
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 Vue Resort & Boathouse

Natura Vue Resort & Boathouse

8/10 Good
"Great location. Clean rooms. Helpful staff"
Lori 1-night trip
Posted 12 hours ago
Natura Vue Resort & Boathouse

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