Southwest Wisconsin Vacation Rentals

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Southwest Wisconsin Vacation Homes

Tamarack Wisconsin Dells a Ramada by Wyndham
Indoor pool, seasonal outdoor pool

Tamarack Wisconsin Dells a Ramada by Wyndham

3.0 star property
9.2 out of 10, Wonderful, (940)
"Pleasant stay and affordable "
Tamarack Wisconsin Dells a Ramada by Wyndham
A Pleasant Retreat- No Cleaning Fee & New Discounts
Exterior

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (215)
"We needed a place for a group of family members to stay to prepare food and decorations for a 60th birthday party at a nearby location. We had everything we needed and our hosts provided other prep items that aren’t commonly found in a rental home. The location was ideal (near a grocery store for forgotten items) and so comfortable!"
A Pleasant Retreat- No Cleaning Fee & New Discounts
Draper Vacation Home - Families & Friends Welcome
Fridge, microwave, oven, stovetop

Draper Vacation Home - Families & Friends Welcome

10.0 out of 10, Exceptional, (21)
"House had a nice few of the city! Very comfortable for all of us. Would recommend booking this gem for a stay in Baraboo. "
The price is CA $210
CA $623 total
includes taxes & fees
Dec 4 - Dec 5
Draper Vacation Home - Families & Friends Welcome
Ohio Street Retreat-hot tub, massage chair, pool
Interior

Ohio Street Retreat-hot tub, massage chair, pool

10.0 out of 10, Exceptional, (43)
"Loved this home. Had everything we needed to make our stay comfortable. The massage chair was icing on the cake! Would highly recommend this place for anyone coming to this area. "
The price is CA $166
CA $277 total
includes taxes & fees
Nov 24 - Nov 25
Ohio Street Retreat-hot tub, massage chair, pool
Gorgeous Log Home featuring 8-person outdoor HOT TUB-available year round.
Outdoor spa tub

Gorgeous Log Home featuring 8-person outdoor HOT TUB-available year round.

10.0 out of 10, Exceptional, (140)
"10/10"
Gorgeous Log Home featuring 8-person outdoor HOT TUB-available year round.
*Luxurious Turkey Run*
Terrace/patio

*Luxurious Turkey Run*

10.0 out of 10, Exceptional, (188)
"We came to town to meet up with our extended families for some horseback riding and bike riding. Great place, perfect for a large group. Great location to food and entertainment, beautiful country cabin. We will come back. "
*Luxurious Turkey Run*
Legendary Moose Lodge
Dining

Legendary Moose Lodge

10.0 out of 10, Exceptional, (250)
"Excellent property and would stay again if the opportunity presents itself."
Legendary Moose Lodge
Spacious Dog Friendly, Near UWL, Washer/Dryer, Fenced-In Yard, Firewood Included
Fridge, microwave, oven, stovetop

Spacious Dog Friendly, Near UWL, Washer/Dryer, Fenced-In Yard, Firewood Included

10.0 out of 10, Exceptional, (20)
"This was a great location to visit my son who attends UW La Crosse. The house had everything we needed and much more. "
The price is CA $222
CA $568 total
includes taxes & fees
Dec 4 - Dec 5
Spacious Dog Friendly, Near UWL, Washer/Dryer, Fenced-In Yard, Firewood Included
Spacious 6 Bedroom less than 10 min walk to Downtown WI Dells! Sleeps 20+!
Fridge, microwave, oven, stovetop

Spacious 6 Bedroom less than 10 min walk to Downtown WI Dells! Sleeps 20+!

2.0 star property
10.0 out of 10, Exceptional, (2)
"It was perfect for our large group, everyone was able to sleep comfortably and also find a space for themselves if they wanted! "
The price is CA $453
CA $1,209 total
includes taxes & fees
Dec 11 - Dec 12
Spacious 6 Bedroom less than 10 min walk to Downtown WI Dells! Sleeps 20+!
Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.
Property grounds

Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.

9.0 out of 10, Wonderful, (73)
"You’ll love it here. Close to many attractions. "
Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.
Great 1 Bedroom unit with easy access to everything
Beach

Great 1 Bedroom unit with easy access to everything

9.6 out of 10, Exceptional, (45)
"Nice small well-cared for and clean home. We enjoyed the new upgrades. Very nice bathroom. Kitchen was a little light on necessities, but we were not cooking too much, so it was not a problem. On-street parking right in front was convenient. Quiet neighbors. We enjoyed our stay."
The price is CA $119
CA $267 total
includes taxes & fees
Dec 21 - Dec 22
Great 1 Bedroom unit with easy access to everything
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Outdoor spa tub

Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

10.0 out of 10, Exceptional, (98)
"Beautiful space, very relaxing. We had a great stay!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Elegant country retreat near Spring Green w expansive views of Driftless Region
Smart TV, DVD player, books

Elegant country retreat near Spring Green w expansive views of Driftless Region

10.0 out of 10, Exceptional, (27)
"Spring Green was a great halfway point for meeting up with friends. Three couples shared this beautiful house for a low key weekend. This unique property had everything we were looking for. The house is well-maintained, was fully stocked (especially the kitchen), and offers a spacious layout. The setting is beautiful. Barbara was a wonderful host."
Elegant country retreat near Spring Green w expansive views of Driftless Region
Hideout Haven
Interior

Hideout Haven

9.8 out of 10, Exceptional, (57)
"House was clean and very close to Baraboo. Perfect for a quick weekend trip."
Hideout Haven
Family friendly house in forest,3min from Castle Rock Lake.25 min from Wis Dells
Property grounds

Family friendly house in forest,3min from Castle Rock Lake.25 min from Wis Dells

10.0 out of 10, Exceptional, (131)
"Great place to stay. Our family consists of my husband & I, plus our 2 sons (33 & 36). We love coming up here, we’re surrounded by trees, so it’s like we’re in the woods. Love seeing the wildlife walk by! Very clean & well maintained. "
Family friendly house in forest,3min from Castle Rock Lake.25 min from Wis Dells
Wooded Bliss @ Spring Brook Resort
Exterior

Wooded Bliss @ Spring Brook Resort

10.0 out of 10, Exceptional, (2)
"We liked the many different spaces we could hang out in. Kitchen layout is great for a large group."
The price is CA $530
CA $1,025 total
includes taxes & fees
Nov 24 - Nov 25
Wooded Bliss @ Spring Brook Resort
The Manor on Green Lake
Property grounds

The Manor on Green Lake

10.0 out of 10, Exceptional, (3)
"The historic home is in a great location in a beautiful lakefront neighborhood and worked perfectly for our family reunion on the lake. The house is classically beautiful inside with a comfortable, relaxed feel. The hosts were very easy to work with and extremely accommodating."
The Manor on Green Lake
Badgerado on Castle Rock Lake Buy 2 get 1 Free
Exterior

Badgerado on Castle Rock Lake Buy 2 get 1 Free

9.2 out of 10, Wonderful, (25)
"We enjoyed our stay at Badgerado. The house had plenty of space for our family. We enjoyed the double oven, and we made full use of the oversize refrigerator. The setting was very nice - semi-private due to all of the trees, and we could easily get to the dock to look out over Castle Rock Lake. It would have been helpful if the list of amenities had been more detailed. We asked the management company if expanded seating, a high chair, and a coffee grinder were available, We were told none of...
Badgerado on Castle Rock Lake Buy 2 get 1 Free
Superior Queen Room With Two Queen Beds Non-Smoking
1 bedroom, iron/ironing board, WiFi, bed sheets

Superior Queen Room With Two Queen Beds Non-Smoking

2.0 out of 10, (1)
The price is CA $110
CA $153 total
includes taxes & fees
Nov 23 - Nov 24
Superior Queen Room With Two Queen Beds Non-Smoking
Lakefront Paradise: New Home in New Lisbon with Endless Activities & Views
Exterior

Lakefront Paradise: New Home in New Lisbon with Endless Activities & Views

8.6 out of 10, Excellent, (8)
Lakefront Paradise: New Home in New Lisbon with Endless Activities & Views
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.
Don't see what you're looking for?
See all available properties in Southwest Wisconsin
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Southwest Wisconsin

Bluegreen Vacations Odyssey Dells Resort
Water park

Bluegreen Vacations Odyssey Dells Resort

3.5 star property
9.2 out of 10, Wonderful, (89)
"Staff was very helpful and friendly. Room was in excellent condition."
Bluegreen Vacations Odyssey Dells Resort
Caribbean Club Resort
Exterior

Caribbean Club Resort

3.0 star property
8.0 out of 10, Very good, (331)
"The condo was very nice and location was very good by the pool "
Caribbean Club Resort
*Pool/Hot Tub| Cozy 2 BR Condo | Waterfront | Downtown | Riverwalk Retreat
Property grounds

*Pool/Hot Tub| Cozy 2 BR Condo | Waterfront | Downtown | Riverwalk Retreat

9.8 out of 10, Exceptional, (135)
"Condo on ground level so a few steps down. Clean and pleasant. Location along river very good. Next to public boat ramp so watched boats come and go. Woderful host!!!! Very quick response and pleasant."
The price is CA $138
CA $403 total
includes taxes & fees
Nov 25 - Nov 26
*Pool/Hot Tub| Cozy 2 BR Condo | Waterfront | Downtown | Riverwalk Retreat
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.
Unlock Black Friday deals