The 30 Best Holiday Rentals in Wisconsin

Ranked 1 out of 545 in the Wisconsin region, as well as being 5 of 83 for holiday rentals in Milwaukee.

• “It was clean.”
• “Location was great”
• “The scene, location, and peace.”
• See more reviews of Flexhome Skywalk to Fiserv 1BR Apt U5 - READ INFO

Ranked 2 out of 545 in the Wisconsin region, as well as being 9 of 83 for holiday rentals in Milwaukee.

• “Fantastic place!”
• “This place was immaculate.”
• “This was a great place to stay!”
• See more reviews of The Bentley Condotel, Heart of Walkers Point with Garage, Yard

Ranked 3 out of 545 in the Wisconsin region, as well as being 3 of 11 for holiday rentals in Fish Creek.

• “Great place to stay. Would stay again.”
• “Will rent again”
• “Perfect for all families walking distance to state park,...”
• See more reviews of Evergreen Hill Condominiums

Ranked 4 out of 545 in the Wisconsin region, as well as being 13 of 83 for holiday rentals in Milwaukee.

• “It was good overall”
• “Great accommodations and location, but loud.”
• “Never again, poor property management”
• See more reviews of Kasa Westown Milwaukee

Ranked 5 out of 545 in the Wisconsin region, as well as being 4 of 19 for holiday rentals in La Crosse.

• “The home was very cute and comfortable!”
• “We loved every minute. We wanted to move in! :-)”
• “Was very clean and inviting and our dog loved the enclosed...”
• See more reviews of Charming, 1-bedroom, open concept house

Ranked 6 out of 545 in the Wisconsin region, as well as being 15 of 83 for holiday rentals in Milwaukee.

• “I had a decent experience.”
• “It was the perfect spot to stay while we caught a Bucks game.”
• “Very happy!”
• See more reviews of Flexhome Skywalk to Fiserv 1BR Apt U3 - READ INFO

Ranked 7 out of 545 in the Wisconsin region, as well as being 2 of 9 for holiday rentals in Hayward.

• “Cozy and comfortable.”
• “We loved the coziness and accommodations.”
• “Were glad we got the place just prior to Birkie, but disappointed in too many items not working or in bad condition”
• See more reviews of Honeybear Hideaway Cabin

Ranked 8 out of 545 in the Wisconsin region, as well as being 3 of 4 for holiday rentals in Egg Harbor.

• “I would stay again, just bring my own towels. I will mention I left an expensive Item behind and they did return it to m”
• “The fall colors in the wooded campground”
• “Great place to glamp !”
• See more reviews of HTR Door County

Ranked 9 out of 545 in the Wisconsin region, as well as being 3 of 9 for holiday rentals in Hayward.

• “Very nice! We will hopefully be renting it again in the future!”
• “Cute little cabin with everything you need.”
• “We cannot wait to book again everything was amazing”
• See more reviews of Lakeshore Lily Pad

Ranked 10 out of 545 in the Wisconsin region, as well as being 5 of 8 for holiday rentals in Baileys Harbor.

• “This place was cleaner than my house!”
• “Pleasant other than shoddy wifi or internet and very uncomfortable beds”
• “It was worth it!”
• See more reviews of Baileys Sunset Cottages

Ranked 11 out of 545 in the Wisconsin region, as well as being 25 of 83 for holiday rentals in Milwaukee.

• “Beautiful apartment, great price, even better location. Loved it!”
• “Over all we had a wonderful time, the apartment lived up to our expectations.”
• “it was nice and small”
• See more reviews of Flexhome Brewery District 2BR Apt M11 - READ INFO

Ranked 12 out of 545 in the Wisconsin region, as well as being 28 of 83 for holiday rentals in Milwaukee.

• “Perfect home for our family of 7 who came Into town to spend time with family for thanksgiving. We loved the home it was”
• “Great location! Cozy home.”
• “Our stay was very pleasant, the house was comfortable and quite well equipt.”
• See more reviews of Comfortable 3 BR Craftsman Bungalow in Milwaukee's Bay View Neighborhood

Ranked 13 out of 545 in the Wisconsin region, as well as being 1 of 1 for holiday rentals in Campbellsport.

• “This was a second stay at this property.”
• “Great condo, great stay!”
• “Very comfortable stay, exceeded our expectations.”
• See more reviews of McJuggers Loft Walk to Lake, Park, Restaurants

Ranked 14 out of 545 in the Wisconsin region, as well as being 1 of 1 for holiday rentals in Fountain City.

• “Sunset on the Mississippi”
• “Nice getaway”
• “Very clean, close to Winona.”
• See more reviews of Riverview Apartment - River Road Historic Home

Ranked 15 out of 545 in the Wisconsin region, as well as being 23 of 67 for holiday rentals in Wisconsin Dells.

• “The beautiful view”
• “I would stay here again.”
• “Overall, very nice property. Will definitely return!”
• See more reviews of Delton Grand Resort

Ranked 16 out of 545 in the Wisconsin region, as well as being 15 of 31 for holiday rentals in Lake Geneva.

• “Great location!”
• “Highly Recommend”
• “It was a home away from home very comfortable didn't...”
• See more reviews of Williams Bay Retreat Walk to Lake Geneva and Town!

Ranked 17 out of 545 in the Wisconsin region, as well as being 18 of 41 for holiday rentals in Green Bay.

• “Great location, clean and great host”
• “Very clean, and very comfortable plush bedding.”
• “Highly recommend and will return!”
• See more reviews of Green Bay Stay

Ranked 18 out of 545 in the Wisconsin region, as well as being 35 of 83 for holiday rentals in Milwaukee.

• “Modern roomy apartment close to Brady street.”
• “We went out for breakfast around the corner and it was...”
• “nice place to live”
• See more reviews of Flexhome Brady District 1BR Apt E1 - READ INFO

Ranked 19 out of 545 in the Wisconsin region, as well as being 26 of 67 for holiday rentals in Wisconsin Dells.

• “We had the best time! There is so much to do: basketball court, pool table, games, fire pit & more!”
• “It is a perfect house to relax in and spent time with family.”
• “Family Fun Home”
• See more reviews of Large Home with Indoor Basketball Court and Game Room!

Ranked 20 out of 545 in the Wisconsin region, as well as being 1 of 1 for holiday rentals in Ontario.

• “We arrived and it was very easy to find the entrance and the key. The room was spacious!”
• “We will definitely be back!”
• “It was enjoyable”
• See more reviews of Hansen House

Ranked 21 out of 545 in the Wisconsin region, as well as being 17 of 31 for holiday rentals in Lake Geneva.

• “We had an amazing time”
• “We would stay again!! :)”
• “Very comfortable,”
• See more reviews of LARGE 5 Bed Lake Geneva Home 4 Blocks from Lake!

Ranked 22 out of 545 in the Wisconsin region, as well as being 46 of 83 for holiday rentals in Milwaukee.

• “Unit has potential but needs several updates.”
• “the apartment was very clean and comfortable”
• “Location and quality amenities”
• See more reviews of Flexhome Economy Studio Apt F1 - READ INFO

Ranked 23 out of 545 in the Wisconsin region, as well as being 30 of 67 for holiday rentals in Wisconsin Dells.

• “The place was very clean and comfortable”
• “Nice getaway”
• “Nice and cozy 1 bedroom unit with all the comforts of home.”
• See more reviews of Light House 603

Ranked 24 out of 545 in the Wisconsin region, as well as being 47 of 83 for holiday rentals in Milwaukee.

• “Best affordable stay in Milwaukee”
• “Everything”
• “Location Cleanliness”
• See more reviews of McKinley Beach Sunrise Studio - Pet Friendly

Ranked 25 out of 545 in the Wisconsin region, as well as being 18 of 31 for holiday rentals in Lake Geneva.

• “Perfect 10/10”
• “Pleasantly surprised!”
• “Our condo was very clean and well equipped. The host was available when needed! We enjoyed our stay”
• See more reviews of Modern Lake Geneva Condo with Year-Round Views

Ranked 26 out of 545 in the Wisconsin region, as well as being 48 of 83 for holiday rentals in Milwaukee.

• “Great little porch and peaceful neighborhood.”
• “Quiet, nice neighborhood, cozy, and clean.”
• “After nearly three weeks in Illinois and Wisconsin (and a testing schedule to boot), this place was perfect to unwind an”
• See more reviews of Cute yellow 2-BR bungalow w/free garage, free WiFi

Ranked 27 out of 545 in the Wisconsin region, as well as being 1 of 1 for holiday rentals in Pound.

• “We saw a gaggle of turkeys, 1 momma deer with 2 babies every...”
• “too short”
• “It was a very peaceful, stress free, enjoyable place.”
• See more reviews of Cabin Near to Lakes, ATVing, Skiing and Natl Forest

Ranked 28 out of 545 in the Wisconsin region, as well as being 1 of 1 for holiday rentals in Ferryville.

• “Loved the cabin, we will be back.”
• “Very clean, nice atmosphere.”
• See more reviews of Cabin by the River Visited by Treehouse Masters!

Ranked 29 out of 545 in the Wisconsin region, as well as being 9 of 13 for holiday rentals in Sheboygan.

• “Perfection! Everything we could have wanted and more!”
• “very comfortable stay”
• “First time at a Airbnb and the best!”
• See more reviews of Riverfront Sheboygan Townhome with Grill!

Ranked 30 out of 545 in the Wisconsin region, as well as being 7 of 9 for holiday rentals in Sister Bay.

• “Excellent location and home! It was super clean and just a great vacation home in a great location!”
• “I definitely would recommend the rental of this home. Great yard and outdoor area!”
• “Location, privacy, space, the welcome basket, everything else”
• See more reviews of Updated Home with Deck 2 Mi to Sister Bay Beach!