Holiday Homes in Southeast Wisconsin

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Featured Holiday Homes in Southeast Wisconsin

Private Country House near Lake Geneva, Como and Williams Bay

10.0 out of 10, Exceptional, (74)
"This was the fourth year in a row that we have stayed at house in the woods. Each year I take my children and grandchildren and this year my first great grandchild a way to Wisconsin for a few days to really bond. This is a perfect place for a large group. We are a group of 20 adults and one infant and there is plenty of room for everyone to sleep comfortably and to be able to get privacy if they want it or otherwise to bond together with game playing and just playing conversations. I can’t...
Private Country House near Lake Geneva, Como and Williams Bay

Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!

10.0 out of 10, Exceptional, (16)
"The property was a good place to stay at! I will say it was what we needed for everyone to stay and have a place to sleep. The only issue with was trying to fit a vehicle in the garage. We took my friends Tahoe and it was a tough spot to fit in the garage, which we can tell it’s meant for smaller vehicles. And there were a pair of eyelashes set out on the coffee table. But overall for anyone with a bigger family or group of friends that need somewhere to stay I would recommend this location!"
The price is AU$881
includes taxes & fees
29 Dec - 30 Dec
Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

10.0 out of 10, Exceptional, (232)
"I booked this property for a reunion with some old friends, with the intention that we would be spending a lot of time hanging out. This property was perfect for that -- lots of beds and bathrooms. A beautiful view of the lake from the main living area and two of the bedrooms. Lots of amenities/activities including a pool table, ping pong, a fire pit, etc. But perhaps the best feature was the openness of the kitchen/dining room/pool table/family room, which meant that you feel connected to...
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

Beach Theme Burlington Retreat

10.0 out of 10, Exceptional, (17)
"We came into town for a wedding and had a great stay! Our family of 4 was comfortable and pleased! "
The price is AU$566
includes taxes & fees
6 Jan - 7 Jan 2025
Beach Theme Burlington Retreat

Modern Home, Fire Pit, Golf Cart Included, Dog Friendly, Sleeps 6

10.0 out of 10, Exceptional, (16)
"Beautiful property and location. One block away from lake. Quiet and peaceful. Exactly what my family and I needed. Great kitchen with all utensils and appliances needed to make a great meal. Cute backyard. Close enough to Geneva for last second shopping for supplies. Nice decor and furnishings. Comfortable beds. Immaculate bathrooms. Will definitely rent this property again. Easy check in process and no long list of restrictions on proper usage. Thank you for letting us stay at your...
Modern Home, Fire Pit, Golf Cart Included, Dog Friendly, Sleeps 6

Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find

9.6 out of 10, Exceptional, (54)
"Home was large and well appointed. Great central location for all the Milwaukee activities we did. "
The price is AU$622
includes taxes & fees
1 Jan - 2 Jan 2025
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find

White House on Wisconsin-Entire Property |Renovated Colonial Revival |Horticultural Hall |Sleeps 20

10.0 out of 10, Exceptional, (5)
"We had a wonderful time at this beautiful home. The location was perfect and within walking distance to the town of Lake Geneva, the lake and steps from a fantastic farmer’s market on Thursday mornings. The thing that stands out is their responsiveness. If we needed to reach out with a question, it was responded to almost immediately. We highly recommend this beautiful home!"
The price is AU$2,409
includes taxes & fees
1 Jan - 2 Jan 2025
White House on Wisconsin-Entire Property |Renovated Colonial Revival |Horticultural Hall |Sleeps 20

Spacious Home Perfect for Families & Groups: Near Fiserv Forum & Brady Street!

10.0 out of 10, Exceptional, (5)
"Property was as described. Clean. Easy check in. Would stay there again."
Spacious Home Perfect for Families & Groups: Near Fiserv Forum & Brady Street!

Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!

9.8 out of 10, Exceptional, (74)
"AMAZING PROPERTY!!!"
The price is AU$879
includes taxes & fees
6 Jan - 7 Jan 2025
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!

𖤓The Blue Store 2000sqft 5BD/2BT Arcade, Pool Table, Foosball, BBQ State Fair𖤓

9.4 out of 10, Exceptional, (25)
"We've stayed here before and then again. Will be back if we need to get back to Wauwatosa. Thank you."
𖤓The Blue Store 2000sqft 5BD/2BT Arcade, Pool Table, Foosball, BBQ State Fair𖤓

Spacious 4 BDR Home in Desirable Abbey Springs! Pool, Beach, Golf, & More

10.0 out of 10, Exceptional, (2)
Spacious 4 BDR Home in Desirable Abbey Springs! Pool, Beach, Golf, & More

#1 - Magnolia · LARGE 5 Bed Lake Geneva Home 4 Blocks from Lake!

9.8 out of 10, Exceptional, (19)
"Large space for 4 guys on golf weekend. Very well organized and communication with the host was great."
The price is AU$856
includes taxes & fees
20 Jan - 21 Jan 2025
#1 - Magnolia · LARGE 5 Bed Lake Geneva Home 4 Blocks from Lake!

Charming Vintage Farmhouse 1 bedroom Garden Oasis

9.2 out of 10, Wonderful, (31)
"First time using VRBO, and everything went well. Excellent communication from property manager including prompt replies when we had some small trouble getting in to the property. Location is great—two blocks to lake. Safe neighborhood. Abundant on-street parking. Unit was clean and comfortable. "
Charming Vintage Farmhouse 1 bedroom Garden Oasis

Sunny 3 BR Craftsman Bungalow | Bay View

10.0 out of 10, Exceptional, (25)
"We had a great time! The house is everything the picture show! Beautiful home with everything you need to stay in!"
Sunny 3 BR Craftsman Bungalow | Bay View

Cozy Lakehouse Views on a hill, Hot tub, water activities, pier, & optional boat

10.0 out of 10, Exceptional, (9)
"Mario and Katie have a beautiful home with all the bells and whistles. We enjoyed the home, the hot tub, multiple patios, the lake and the low key vibe. The introduction to Luke at Luke's Float and Boat for our pontoon was a great add! Enjoy your time at the lake!"
Cozy Lakehouse Views on a hill, Hot tub, water activities, pier, & optional boat

MKE Riverwest Retreat - Newly Renovated

10.0 out of 10, Exceptional, (2)
"Firstly the host made this stay a breeze! Host communicated with me for the booking process, gave plenty of information regarding the area and the house, and had the listing for a fair price. The house itself is awesome! Selection of games was great especially for our group (we play a lot of board and card games), the TV in the living room was quality, the entire house was spotless when we arrived. Everything in the house was too notch condition, great kitchen, everything was well labeled and...
MKE Riverwest Retreat - Newly Renovated

Historic Retreat - steps from the Lake and Downtown

10.0 out of 10, Exceptional, (24)
"We had a very nice weekend staying at the Maxwell House! The renovations in the home are beautiful, there is a lot of space, and the location is perfect! We were blessed with good weather, so we walked all over town. We hope to come back again. "
Historic Retreat - steps from the Lake and Downtown

Cottage walking distance to Lake Geneva!

10.0 out of 10, Exceptional, (32)
"The cottage was very nice. We enjoyed the stay well worth it."
Cottage walking distance to Lake Geneva!

Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

9.6 out of 10, Exceptional, (78)
"It was a very nice place. Clean and cute. It would have helped to have the porch light on since arrived at night. We were a little unsure of where to go but figured it out because of the pictures. "
The price is AU$163
includes taxes & fees
29 Dec - 30 Dec
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

Quaint Sleep 8 In Downtown Walk to Lake Pets OK

9.6 out of 10, Exceptional, (49)
"My family and I went for a quick weekend getaway for my birthday. The location was perfect for us to have easy access to downtown Lake Geneva. The price was right. And we really like the Calamari Cafe down the street."
Quaint Sleep 8 In Downtown Walk to Lake Pets OK
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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Other property types in Southeast Wisconsin

Timber Ridge Lodge and Waterpark

3.5 star property
8.6 out of 10, Excellent, (2605)
"Amazing place "
The price is AU$278
includes taxes & fees
9 Jan - 10 Jan 2025
Timber Ridge Lodge and Waterpark

The Plaza Hotel

3.0 star property
8.6 out of 10, Excellent, (1053)
"Great for kitchenettes and proximity to Milwaukee Museum of Art."
The price is AU$302
includes taxes & fees
29 Dec - 30 Dec
The Plaza Hotel

Kasa Westown Milwaukee

4.0 star property
9.0 out of 10, Wonderful, (66)
"Would've preferred a tv in the bedroom too and an additional comforter for the sofa bed. Other than that, it was pretty good. "
The price is AU$198
includes taxes & fees
6 Jan - 7 Jan 2025
Kasa Westown Milwaukee
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.