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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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 473
AED 789 total
includes taxes & fees
6 Oct - 7 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, (46 reviews)
"Brady was very prompt and the stay exceeded expectations We plan to stay again very soon! Thank you, Brady!"
United States
Josias F.
The price is AED 335
AED 431 total
includes taxes & fees
12 Oct - 13 Oct
Tamarack Point Homestead
A single-story house with a gabled roof, a front porch, and a small front yard with mulch and plants.

3. 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
8 Oct - 9 Oct
Colorful getaway in friendly Driftless village
A modern kitchen with a central island, stainless steel appliances, and wooden flooring.

4. 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)
"Was a very nice and quiet place to relax and enjoy. Comfortable beds and very nice interior"
United States
nate k.
The price is AED 436
AED 787 total
includes taxes & fees
1 Nov - 2 Nov
Ohio Street Retreat-hot tub, pool, massage chair
A living room with a TV, wooden furniture, a dining table with chairs, and a kitchen in the background.

5. 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)
"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."
United States
Roger S.
The price is AED 547
AED 1,184 total
includes taxes & fees
2 Nov - 3 Nov
Large 2-bedroom lower unit with fast WI-FI & in unit washer/dryer
A bedroom with a vanity, a large mirror, a bed, and a nightstand with a lamp.

6. 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)
"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 917 total
includes taxes & fees
18 Oct - 19 Oct
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Living area

7. Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (123 reviews)
"Super cute and cozy place - perfect for our getaway. "
United States
Katie K.
The price is AED 565
AED 852 total
includes taxes & fees
11 Oct - 12 Oct
Serenity Cottage at Mineral Point
A modern living room with a staircase, a dark door, a grey armchair, and a coffee table with decorative items.

8. The Honey Haven

The Honey Haven
Westby
10.0 out of 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."
United States
Eric R.
The Honey Haven
A kitchen with a sliding glass door leading to a wooden deck with a view of a grassy field and a lake.

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, (44 reviews)
"Very clean property, exactly as advertised. Host was easy to work with."
United States
Jacob M.
The price is AED 657
AED 1,248 total
includes taxes & fees
14 Oct - 15 Oct
Updated home with lake views, across the street from Lake WI, near free ferry
Property grounds

10. 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
7 Oct - 8 Oct
Remodeled, cozy, pet friendly cabin near lakes
A covered outdoor area with a table and chairs, a view of a lake, and docked boats.

11. Dells Lake Villa - Lake Front Luxury

Dells Lake Villa - Lake Front Luxury
Lake Delton
9.6 out of 10, Exceptional, (13 reviews)
"Nice property and close to many of the Dells attractions."
United States
Mark V.
The price is AED 477
AED 1,288 total
includes taxes & fees
26 Oct - 27 Oct
Dells Lake Villa - Lake Front Luxury
A multi-story hotel with a pool area and a beach.

12. Dells Paradise At Lighthouse Cove Condominiums

Dells Paradise At Lighthouse Cove Condominiums
Lake Delton
9.6 out of 10, Exceptional, (20 reviews)
"My friends and I enjoyed our stay here. "
United States
Haily A.
The price is AED 511
AED 1,327 total
includes taxes & fees
3 Nov - 4 Nov
Dells Paradise At Lighthouse Cove Condominiums
A bedroom with a bed, a television mounted on the wall, a window with blinds, and a closet with shelves.

13. Draper Vacation Home - Families & Friends Welcome

Draper Vacation Home - Families & Friends Welcome
Baraboo
10.0 out of 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."
United States
Michele T.
The price is AED 652
AED 1,799 total
includes taxes & fees
13 Oct - 14 Oct
Draper Vacation Home - Families & Friends Welcome
A single-story house with a front porch, a garage, and a small shed in a grassy yard surrounded by trees.

14. 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)
"Great home and host beautiful home "
United States
Michael C.
The price is AED 393
AED 1,255 total
includes taxes & fees
6 Oct - 7 Oct
Fawn Lake Cottage for Families Looking for Privacy
A two-story house with a deck, outdoor seating area, and a fire pit.

15. Lakefront Luxury | Near WI Dells

Lakefront Luxury | Near WI Dells
Mauston
9.8 out of 10, Exceptional, (10 reviews)
"Place was very clean and there were beautiful sunsets!"
United States
Catherine K.
The price is AED 472
AED 1,885 total
includes taxes & fees
6 Oct - 7 Oct
Lakefront Luxury | Near WI Dells
A family standing in front of a stone building with a wooden porch and a number '816' above the entrance.

16. 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
6 Oct - 7 Oct
Hamilton Goebel House 816 E Louisa St Darlington Wi
A wooden deck with a bench, a white door, and hanging flower baskets.

17. 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)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is AED 511
AED 645 total
includes taxes & fees
19 Oct - 20 Oct
The Bungaleau 1 Bedroom House In Cute Rivertown
A hallway with a wooden door leading to a kitchen area.

18. 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 869
AED 2,933 total
includes taxes & fees
12 Oct - 13 Oct
Cozy Luxe Retreat| High-End Design w/outdoor fire pit WI Dells, Cascade MT, Devils Lake
A serene lakeside setting with a wooden dock extending into the water, surrounded by lush greenery and trees.

19. Lake Cottage 30 minutes from Wisconsin Dells.

Lake Cottage 30 minutes from Wisconsin Dells.
Friendship
9.8 out of 10, Exceptional, (62 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
7 Oct - 8 Oct
Lake Cottage 30 minutes from Wisconsin Dells.
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, (177 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
6 Oct - 7 Oct
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

Amber's Inn & Suites

Amber's Inn & Suites

10/10 Excellent
"Very nice quiet area but close enough to walk to downtown entertainment if you wish to. Have stayed here several times and is always a pleasant experience."
Julia 2-night trip
Posted less than an hour ago
Amber's Inn & Suites

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